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  Subjects -> ENGINEERING (Total: 2266 journals)
    - CHEMICAL ENGINEERING (190 journals)
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    - ENGINEERING (1197 journals)
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ENGINEERING (1197 journals)                  1 2 3 4 5 6 | Last

Showing 1 - 200 of 1205 Journals sorted alphabetically
3 Biotech     Open Access   (Followers: 7)
3D Research     Hybrid Journal   (Followers: 19)
AAPG Bulletin     Full-text available via subscription   (Followers: 5)
AASRI Procedia     Open Access   (Followers: 14)
Abstract and Applied Analysis     Open Access   (Followers: 3)
Aceh International Journal of Science and Technology     Open Access   (Followers: 2)
ACS Nano     Full-text available via subscription   (Followers: 207)
Acta Geotechnica     Hybrid Journal   (Followers: 6)
Acta Metallurgica Sinica (English Letters)     Hybrid Journal   (Followers: 5)
Acta Polytechnica : Journal of Advanced Engineering     Open Access   (Followers: 1)
Acta Scientiarum. Technology     Open Access   (Followers: 3)
Acta Universitatis Cibiniensis. Technical Series     Open Access  
Active and Passive Electronic Components     Open Access   (Followers: 7)
Adaptive Behavior     Hybrid Journal   (Followers: 10)
Adıyaman Üniversitesi Mühendislik Bilimleri Dergisi     Open Access  
Adsorption     Hybrid Journal   (Followers: 4)
Advanced Engineering Forum     Full-text available via subscription   (Followers: 4)
Advanced Science     Open Access   (Followers: 4)
Advanced Science Focus     Free   (Followers: 3)
Advanced Science Letters     Full-text available via subscription   (Followers: 4)
Advanced Science, Engineering and Medicine     Partially Free   (Followers: 6)
Advanced Synthesis & Catalysis     Hybrid Journal   (Followers: 17)
Advances in Artificial Neural Systems     Open Access   (Followers: 3)
Advances in Calculus of Variations     Hybrid Journal   (Followers: 2)
Advances in Catalysis     Full-text available via subscription   (Followers: 5)
Advances in Complex Systems     Hybrid Journal   (Followers: 7)
Advances in Engineering Software     Hybrid Journal   (Followers: 25)
Advances in Fuel Cells     Full-text available via subscription   (Followers: 14)
Advances in Fuzzy Systems     Open Access   (Followers: 5)
Advances in Geosciences (ADGEO)     Open Access   (Followers: 9)
Advances in Heat Transfer     Full-text available via subscription   (Followers: 18)
Advances in Human Factors/Ergonomics     Full-text available via subscription   (Followers: 22)
Advances in Magnetic and Optical Resonance     Full-text available via subscription   (Followers: 7)
Advances in Natural Sciences: Nanoscience and Nanotechnology     Open Access   (Followers: 28)
Advances in Operations Research     Open Access   (Followers: 11)
Advances in OptoElectronics     Open Access   (Followers: 5)
Advances in Physics Theories and Applications     Open Access   (Followers: 13)
Advances in Polymer Science     Hybrid Journal   (Followers: 40)
Advances in Porous Media     Full-text available via subscription   (Followers: 4)
Advances in Remote Sensing     Open Access   (Followers: 34)
Advances in Science and Research (ASR)     Open Access   (Followers: 6)
Aerobiologia     Hybrid Journal   (Followers: 1)
African Journal of Science, Technology, Innovation and Development     Hybrid Journal   (Followers: 4)
AIChE Journal     Hybrid Journal   (Followers: 28)
Ain Shams Engineering Journal     Open Access   (Followers: 5)
Akademik Platform Mühendislik ve Fen Bilimleri Dergisi     Open Access  
Alexandria Engineering Journal     Open Access  
AMB Express     Open Access   (Followers: 1)
American Journal of Applied Sciences     Open Access   (Followers: 28)
American Journal of Engineering and Applied Sciences     Open Access   (Followers: 11)
American Journal of Engineering Education     Open Access   (Followers: 9)
American Journal of Environmental Engineering     Open Access   (Followers: 16)
American Journal of Industrial and Business Management     Open Access   (Followers: 23)
Analele Universitatii Ovidius Constanta - Seria Chimie     Open Access  
Annals of Combinatorics     Hybrid Journal   (Followers: 3)
Annals of Pure and Applied Logic     Open Access   (Followers: 2)
Annals of Regional Science     Hybrid Journal   (Followers: 7)
Annals of Science     Hybrid Journal   (Followers: 7)
Applicable Algebra in Engineering, Communication and Computing     Hybrid Journal   (Followers: 2)
Applicable Analysis: An International Journal     Hybrid Journal   (Followers: 1)
Applied Catalysis A: General     Hybrid Journal   (Followers: 5)
Applied Catalysis B: Environmental     Hybrid Journal   (Followers: 6)
Applied Clay Science     Hybrid Journal   (Followers: 4)
Applied Computational Intelligence and Soft Computing     Open Access   (Followers: 12)
Applied Magnetic Resonance     Hybrid Journal   (Followers: 3)
Applied Nanoscience     Open Access   (Followers: 8)
Applied Numerical Mathematics     Hybrid Journal   (Followers: 5)
Applied Physics Research     Open Access   (Followers: 4)
Applied Sciences     Open Access   (Followers: 3)
Applied Spatial Analysis and Policy     Hybrid Journal   (Followers: 4)
Arabian Journal for Science and Engineering     Hybrid Journal   (Followers: 5)
Archives of Computational Methods in Engineering     Hybrid Journal   (Followers: 4)
Archives of Foundry Engineering     Open Access  
Archives of Thermodynamics     Open Access   (Followers: 8)
Arkiv för Matematik     Hybrid Journal   (Followers: 1)
ASEE Prism     Full-text available via subscription   (Followers: 2)
Asian Engineering Review     Open Access  
Asian Journal of Applied Science and Engineering     Open Access   (Followers: 1)
Asian Journal of Applied Sciences     Open Access   (Followers: 2)
Asian Journal of Biotechnology     Open Access   (Followers: 7)
Asian Journal of Control     Hybrid Journal  
Asian Journal of Current Engineering & Maths     Open Access  
Asian Journal of Technology Innovation     Hybrid Journal   (Followers: 9)
Assembly Automation     Hybrid Journal   (Followers: 2)
at - Automatisierungstechnik     Hybrid Journal   (Followers: 1)
ATZagenda     Hybrid Journal  
ATZextra worldwide     Hybrid Journal  
Australasian Physical & Engineering Sciences in Medicine     Hybrid Journal   (Followers: 1)
Australian Journal of Multi-Disciplinary Engineering     Full-text available via subscription   (Followers: 2)
Autonomous Mental Development, IEEE Transactions on     Hybrid Journal   (Followers: 7)
Avances en Ciencias e Ingeniería     Open Access  
Balkan Region Conference on Engineering and Business Education     Open Access   (Followers: 1)
Bangladesh Journal of Scientific and Industrial Research     Open Access  
Basin Research     Hybrid Journal   (Followers: 3)
Batteries     Open Access   (Followers: 3)
Bautechnik     Hybrid Journal   (Followers: 1)
Bell Labs Technical Journal     Hybrid Journal   (Followers: 24)
Beni-Suef University Journal of Basic and Applied Sciences     Open Access   (Followers: 3)
BER : Manufacturing Survey : Full Survey     Full-text available via subscription   (Followers: 2)
BER : Motor Trade Survey     Full-text available via subscription   (Followers: 1)
BER : Retail Sector Survey     Full-text available via subscription   (Followers: 2)
BER : Retail Survey : Full Survey     Full-text available via subscription   (Followers: 2)
BER : Survey of Business Conditions in Manufacturing : An Executive Summary     Full-text available via subscription   (Followers: 3)
BER : Survey of Business Conditions in Retail : An Executive Summary     Full-text available via subscription   (Followers: 3)
Bharatiya Vaigyanik evam Audyogik Anusandhan Patrika (BVAAP)     Open Access   (Followers: 1)
Biofuels Engineering     Open Access  
Biointerphases     Open Access   (Followers: 1)
Biomaterials Science     Full-text available via subscription   (Followers: 8)
Biomedical Engineering     Hybrid Journal   (Followers: 16)
Biomedical Engineering and Computational Biology     Open Access   (Followers: 13)
Biomedical Engineering Letters     Hybrid Journal   (Followers: 5)
Biomedical Engineering, IEEE Reviews in     Full-text available via subscription   (Followers: 16)
Biomedical Engineering, IEEE Transactions on     Hybrid Journal   (Followers: 31)
Biomedical Engineering: Applications, Basis and Communications     Hybrid Journal   (Followers: 5)
Biomedical Microdevices     Hybrid Journal   (Followers: 8)
Biomedical Science and Engineering     Open Access   (Followers: 4)
Biomedizinische Technik - Biomedical Engineering     Hybrid Journal  
Biomicrofluidics     Open Access   (Followers: 4)
BioNanoMaterials     Hybrid Journal   (Followers: 1)
Biotechnology Progress     Hybrid Journal   (Followers: 39)
Boletin Cientifico Tecnico INIMET     Open Access  
Botswana Journal of Technology     Full-text available via subscription  
Boundary Value Problems     Open Access   (Followers: 1)
Brazilian Journal of Science and Technology     Open Access   (Followers: 2)
Broadcasting, IEEE Transactions on     Hybrid Journal   (Followers: 10)
Bulletin of Canadian Petroleum Geology     Full-text available via subscription   (Followers: 14)
Bulletin of Engineering Geology and the Environment     Hybrid Journal   (Followers: 3)
Bulletin of the Crimean Astrophysical Observatory     Hybrid Journal  
Cahiers, Droit, Sciences et Technologies     Open Access  
Calphad     Hybrid Journal  
Canadian Geotechnical Journal     Full-text available via subscription   (Followers: 14)
Canadian Journal of Remote Sensing     Full-text available via subscription   (Followers: 40)
Case Studies in Engineering Failure Analysis     Open Access   (Followers: 7)
Case Studies in Thermal Engineering     Open Access   (Followers: 4)
Catalysis Communications     Hybrid Journal   (Followers: 6)
Catalysis Letters     Hybrid Journal   (Followers: 3)
Catalysis Reviews: Science and Engineering     Hybrid Journal   (Followers: 8)
Catalysis Science and Technology     Free   (Followers: 6)
Catalysis Surveys from Asia     Hybrid Journal   (Followers: 3)
Catalysis Today     Hybrid Journal   (Followers: 5)
CEAS Space Journal     Hybrid Journal  
Cellular and Molecular Neurobiology     Hybrid Journal   (Followers: 4)
Central European Journal of Engineering     Hybrid Journal   (Followers: 1)
CFD Letters     Open Access   (Followers: 6)
Chaos : An Interdisciplinary Journal of Nonlinear Science     Hybrid Journal   (Followers: 2)
Chaos, Solitons & Fractals     Hybrid Journal   (Followers: 3)
Chinese Journal of Catalysis     Full-text available via subscription   (Followers: 2)
Chinese Journal of Engineering     Open Access   (Followers: 2)
Chinese Science Bulletin     Open Access   (Followers: 1)
Ciencia e Ingenieria Neogranadina     Open Access  
Ciencia en su PC     Open Access   (Followers: 1)
Ciencias Holguin     Open Access   (Followers: 1)
CienciaUAT     Open Access  
Cientifica     Open Access  
CIRP Annals - Manufacturing Technology     Full-text available via subscription   (Followers: 10)
CIRP Journal of Manufacturing Science and Technology     Full-text available via subscription   (Followers: 13)
City, Culture and Society     Hybrid Journal   (Followers: 20)
Clay Minerals     Full-text available via subscription   (Followers: 9)
Clean Air Journal     Full-text available via subscription   (Followers: 2)
Coal Science and Technology     Full-text available via subscription   (Followers: 4)
Coastal Engineering     Hybrid Journal   (Followers: 10)
Coastal Engineering Journal     Hybrid Journal   (Followers: 3)
Coatings     Open Access   (Followers: 2)
Cogent Engineering     Open Access   (Followers: 2)
Cognitive Computation     Hybrid Journal   (Followers: 4)
Color Research & Application     Hybrid Journal   (Followers: 1)
COMBINATORICA     Hybrid Journal  
Combustion Theory and Modelling     Hybrid Journal   (Followers: 13)
Combustion, Explosion, and Shock Waves     Hybrid Journal   (Followers: 13)
Communications Engineer     Hybrid Journal   (Followers: 1)
Communications in Numerical Methods in Engineering     Hybrid Journal   (Followers: 2)
Components, Packaging and Manufacturing Technology, IEEE Transactions on     Hybrid Journal   (Followers: 23)
Composite Interfaces     Hybrid Journal   (Followers: 5)
Composite Structures     Hybrid Journal   (Followers: 241)
Composites Part A : Applied Science and Manufacturing     Hybrid Journal   (Followers: 174)
Composites Part B : Engineering     Hybrid Journal   (Followers: 215)
Composites Science and Technology     Hybrid Journal   (Followers: 160)
Comptes Rendus Mécanique     Full-text available via subscription   (Followers: 2)
Computation     Open Access  
Computational Geosciences     Hybrid Journal   (Followers: 12)
Computational Optimization and Applications     Hybrid Journal   (Followers: 7)
Computational Science and Discovery     Full-text available via subscription   (Followers: 2)
Computer Applications in Engineering Education     Hybrid Journal   (Followers: 6)
Computer Science and Engineering     Open Access   (Followers: 17)
Computers & Geosciences     Hybrid Journal   (Followers: 25)
Computers & Mathematics with Applications     Full-text available via subscription   (Followers: 5)
Computers and Electronics in Agriculture     Hybrid Journal   (Followers: 4)
Computers and Geotechnics     Hybrid Journal   (Followers: 8)
Computing and Visualization in Science     Hybrid Journal   (Followers: 6)
Computing in Science & Engineering     Full-text available via subscription   (Followers: 25)
Conciencia Tecnologica     Open Access  
Concurrent Engineering     Hybrid Journal   (Followers: 3)
Continuum Mechanics and Thermodynamics     Hybrid Journal   (Followers: 6)
Control and Dynamic Systems     Full-text available via subscription   (Followers: 7)
Control Engineering Practice     Hybrid Journal   (Followers: 40)
Control Theory and Informatics     Open Access   (Followers: 7)
Corrosion Science     Hybrid Journal   (Followers: 24)
CT&F Ciencia, Tecnologia y Futuro     Open Access  
CTheory     Open Access  
Current Applied Physics     Full-text available via subscription   (Followers: 4)

        1 2 3 4 5 6 | Last

Journal Cover Advanced Synthesis & Catalysis
  [SJR: 2.729]   [H-I: 121]   [17 followers]  Follow
   Hybrid Journal Hybrid journal (It can contain Open Access articles)
   ISSN (Print) 1615-4150 - ISSN (Online) 1615-4169
   Published by John Wiley and Sons Homepage  [1616 journals]
  • Auto-Tandem Catalysis-Induced Synthesis of Trisubstituted Furans through
           Domino Acid-Acid-Catalyzed Reaction of Aliphatic Aldehydes and
           1,3-Dicarbonyl Compounds by using N-Bromosuccinimide as Oxidant
    • Authors: Wenbo Huang; Changhui Liu, Yanlong Gu
      Abstract: The front cover picture, provided by Yanlong Gu and co-workers, illustrates the development of a method to synthesize 2,3,5-trisubstituted furans from two readily available precursors, aliphatic aldehydes and 1,3-dicarbonyl compounds. This method was established on the basis of using N-bromosuccinimide as an oxidizing reagent and aluminum(III) chloride as a catalyst. An acid-acid-catalyzed tandem reaction with auto-tandem catalysis was involved in the reaction mechanism. Details can be found in the communication on pages XXXX–XXXX (W. Huang, C. Liu, Y. Gu, Adv. Synth. Catal. 2017, 359, XXXX–XXXX;
      DOI : 10.1002/adsc.201700074).
      PubDate: 2017-03-21T08:01:07.011365-05:
  • Treasure-Hunting under Cp*Co Catalysis
    • Authors: Tatsuhiko Yoshino; Shigeki Matsunaga
      Abstract: The front cover image, provided by Tatsuhiko Yoshino and Shigeki Matsunaga, illustrates the concept that Cp*Co catalysts are much less expensive than Cp*Rh catalysts (= difference in toll), produce not only the same products (= known treasures), but also different unique new products (= closed unknown treasure boxes), which were never available with previous Cp*Rh catalysts. Details can be found in the review on pages XXXX–XXXX (T. Yoshino, S. Matsunaga, Adv. Synth. Catal. 2017, 359, XXXX–XXXX;
      DOI 10.1002/adsc.201700042).
      PubDate: 2017-03-21T08:01:04.442044-05:
  • Rapid access to indeno[1,2-c]quinolines via Brønsted-Acid Catalyzed
           Cascade Reaction
    • Authors: Sivasenthilkumar Boominathan
      Abstract: A Brønsted acid catalyzed annulation strategy has been developed to construct indeno[1,2-c]quinolines. This tandem synthetic method proceeds through a sequential electrophilic addition followed by a Friedel-Crafts type reaction. A variety of tetracyclic compounds were obtained in moderate to high yields under mild reaction conditions in a short time.
      PubDate: 2017-03-21T03:20:32.696652-05:
      DOI: 10.1002/adsc.201700190
  • Chiral squaramide catalyzed enantioselective decarboxylative addition of
           β-ketoacids to isatin imine
    • Authors: Jasneet Kaur; Anita Kumari, Vimal Bhardwaj, Swapandeep Chimni
      Abstract: An efficient chiral squaramide catalyzed enantioselective decarboxylative addition reaction of β-ketoacids to isatin imines has been developed. The reaction proceeds smoothly using 20 mol% of organocatalyst to afford the chiral 3-aminooxindoles in high yield and excellent enantioselectivity.
      PubDate: 2017-03-21T02:20:29.791669-05:
      DOI: 10.1002/adsc.201700011
  • Chiral N-Heterocyclic Carbene-Catalyzed Asymmetric
           Michael–Intramolecular Aldol-Lactonization Cascade for Enantioselective
           Construction of β-Propiolactone-Fused Spiro[cyclopentane-oxindoles]
    • Authors: Jun-Qi Zhang; Nai-Kai Li, Shao-Jie Yin, Bing-Bing Sun, Wei-Tai Fan, Xing-Wang Wang
      Abstract: A cascade asymmetric Michael–intramolecular aldol-lactonization of enals with oxindolyl β,γ-unsaturated α-keto esters was developed. An optically pure aminoindanol-derived triazolium-based N-heterocyclic carbene was used as the catalyst. The corresponding desired β-propiolactone-fused spiro[cyclopentane-oxindoles] were obtained in moderate yields with excellent diastereoselectivities and enantioselectivities. Notably, the obtained enantio-enriched highly functionalized complex molecules contain four contiguous stereocenters, including a spiro all-carbon center and a quaternary carbon center.
      PubDate: 2017-03-20T08:00:30.660874-05:
      DOI: 10.1002/adsc.201601259
  • Photosensitizer-Free, Gold-Catalyzed C–C Cross-Coupling of Boronic Acids
           and Diazonium Salts Enabled by Visible Light
    • Authors: Sina Witzel; Jin Xie, Matthias Rudolph, A. Stephen K. Hashmi
      Abstract: The first photosensitizer-free visible light-driven, gold-catalyzed C–C cross-couplings of arylboronic acids and aryldiazonium salts are reported. The reactions can be conducted under very mild conditions, using a catalytic amount of tris(4-trifluoromethyl)phosphinegold(I) chloride [(4-CF3-C6H4)3PAuCl] with methanol as the solvent allowing an alternative access to a variety of substituted biaryls in moderate to excellent yields with broad functional group tolerance.
      PubDate: 2017-03-20T07:55:54.417099-05:
      DOI: 10.1002/adsc.201700121
  • One-Pot Sequential N-Heterocyclic Carbene/Rhodium(III) Catalysis:
           Synthesis of Fused Polycyclic Isocoumarins
    • Authors: So Won Youn; Huen Ji Yoo
      Abstract: A one-pot sequential N-heterocyclic carbene–rhodium (NHC-Rh) catalysis is described, demonstrating the compatibility of NHC and Rh catalysts. N-Heterocyclic carbene-catalyzed aerobic oxidation of benzaldehydes and subsequent rhodium(III)-catalyzed oxidative coupling/annulation with multiple bonds enabled the formation of two C–O bonds and one C–C bond in a single pot. This operationally easy, one-pot protocol under air provides access to a diverse array of valuable fused polycyclic isocoumarins.
      PubDate: 2017-03-20T07:55:50.69146-05:0
      DOI: 10.1002/adsc.201700072
  • Intramolecular Direct Arylation of 1,3-Diketone-Derived Enol Ethers in a
           Synthesis of Tricyclic Oxoisochromene Derivatives
    • Authors: Eoin Ó Muimhneacháin; Leticia M. Pardo, Lorraine M. Bateman, U. B. Rao Khandavilli, Simon E. Lawrence, Gerard P. McGlacken
      Abstract: A synthesis of tricyclic oxoisochromene derivatives via an intramolecular direct arylation of cycloalkyl-1,3-diketone-derived α,β-unsaturated ketone substrates is described. Interesting mechanistic insight has been gathered, based on deuterium migration studies, induced by palladium (Pd).
      PubDate: 2017-03-20T07:55:46.211583-05:
      DOI: 10.1002/adsc.201700062
  • Selective Palladium-Catalyzed Domino Heck/Buchwald–Hartwig Arylations of
           N-Glycosylcinnamamides: An Efficient Route to
    • Authors: Thi Thanh Huyen Luong; Sabrina Touchet, Mouad Alami, Samir Messaoudi
      Abstract: An efficient and selective domino Heck/Buchwald–Hartwig arylations of readily available N-glycosylcinnamamides with aryl iodides have been established. Using palladium(II) acetate as a catalyst, potassium acetate as the base and tetrabutylamonium bromide as an additive in dioxane, the protocol proved to be general, and a variety of 4-aryl-N-glycosylquinolin-2-ones has been prepared in good yields with exclusive α- or β-selectivity.
      PubDate: 2017-03-20T07:55:41.956991-05:
      DOI: 10.1002/adsc.201601382
  • Vinylogous Nucleophilic Substitution of the Hydroxy Group in
           Diarylmethanols with 3-Propenyl-2-silyloxyindoles: Towards the Synthesis
           of α-Alkylidene-δ-diaryl-2-oxindoles
    • Authors: Amol P. Jadhav; Amjad Ali, Ravi P. Singh
      Abstract: We report herein a highly stereoselective method for the indium triflate-catalyzed vinylogous substitution of the hydroxy group of diarylmethyl alcohols with 3-alkenyl-2-silyloxyindoles, which affords broadly substituted α-alkylidene-δ-diaryl-2-oxindole products with high efficiency and complete γ-site and Z-selectivity. The reaction displays very wide substrate scopes for both the reactants, benzhydryl alcohols and 3-alkenyl-2-silyloxyindoles. The utility of the substituted adducts is shown by their conversion to other useful derivatives.
      PubDate: 2017-03-20T07:55:34.771368-05:
      DOI: 10.1002/adsc.201601265
  • Amine-Triggered 6π-Electrocyclization–Aromatization Cascade of
    • Authors: Xijian Li; Huidong Yu, Yong Huang
      Abstract: An unprecedented 6π-electrocyclization–aromatization cascade reaction of ynedienamines is described. The electron-rich ynedienamine is converted by γ-protonation to an electrophilic allenyl iminium species which is susceptible to amine addition generating a highly electron-rich triene intermediate. The 6π-electrocyclization is accelerated by three electron-donating substituents in a captodative manner. Subsequent redox-neutral aromatization allows the direct synthesis of 1,3-diaminobenzenes from readily available ynedienamines.
      PubDate: 2017-03-20T07:55:29.782462-05:
      DOI: 10.1002/adsc.201601146
  • Nickel Catalysis Enables Hetero [2+2+1] Cycloaddition between
           Yne-Isothiocyanates and Isonitriles with Low Catalyst Loading
    • Authors: Rui-Juan Liu; Peng-Fei Wang, Wen-Kui Yuan, Li-Rong Wen, Ming Li
      Abstract: Nickel(II) can be used to catalyze the hetero [2+2+1] cycloaddition of 2-alkynylaryl isothiocyanates and isonitriles in 2-methyltetrahydrofuran (2-MeTHF) to give a wide array of thieno[2,3-b]indoles in excellent yields. The reaction is featured by employing as little as 0.3 mol% nickel(II) acetylacetonate [Ni(acac)2] under air conditions in the absence of any additives (additional reducing agents and external ligands). This is the first successful example to apply nickel(II) directly in hetero [2+2+1] cycloadditions.
      PubDate: 2017-03-20T07:55:25.495341-05:
      DOI: 10.1002/adsc.201601271
  • Formation of Spirooxindoles Iodonium from N-Substituted
           3-Oxopentanediamides via Phenyliodine Bis(trifluoroacetate)-Mediated
           Oxidative Cascade Reactions
    • Authors: Yunfei Du; Bei Hu, Yang Cao, Bobo Zhang, Daisy Zhang-Negrerie
      Abstract: The reaction of N-substituted 3-oxopentanediamides with phenyliodine bis(trifluoroacetate) (PIFA) was found to give a novel class of spirooxindole iodonium compounds under metal-free conditions. The reaction is postulated to undergo a cascade process involving an oxidative C-O bond formation, an oxidative C-C bond formation and a final iodination step.
      PubDate: 2017-03-20T02:15:25.318286-05:
      DOI: 10.1002/adsc.201700075
  • N,N’-Dioxide–Lanthanum(III)-Catalyzed Asymmetric Cyclopropanation of
           2-Cyano-3-arylacrylates with 2-Bromomalonates
    • Authors: Yuheng Zhang; Lili Lin, yushuang Chen, Xiaohua Liu
      Abstract: An efficient N,N’-dioxide–lanthanum(III) complex catalytic system has been developed for the diastereo- and enantioselective Michael-initiated ring-closure (MIRC) reaction of 2-cyano-3-arylacrylates with 2-bromomalonates. Various chiral cyclopropanes with multi-substitutions were obtained in high yields (up to 93%) with excellent diastereoselectivities (> 95:5 d.r.) and good enantioselectivities (up to 91% ee). The catalytic system also works for the synthesis of chiral cyclopropane through tandem halogenation/asymmetric MIRC reaction of α,β-unsaturated nitrile with malonate and NBS. Besides, a potential catalytic model was proposed to explain the origin of stereoselectivity.
      PubDate: 2017-03-20T02:00:32.249598-05:
      DOI: 10.1002/adsc.201700212
  • Mild Base-Promoted Indole Annulation–Oxidative Cross- Coupling of
           2-Nitrocinnamaldehydes with β-Tetralones for 3-Naphthylindole and
           3-Naphthylbenzo[g]indole Fluorophores
    • Authors: Tej Narayan Poudel; Yong Rok Lee
      Abstract: This paper describes the transition metal-free indole annulation–oxidative cross-coupling of 2-nitrocinnamaldehydes or (E)-3-(1-nitronaphthalen-2-yl)acrylaldehyde with β-tetralones for the construction of diverse 3-naphthylindole and 3-naphthylbenzo[g]indole fluorophores in moderate to good yields. This unique annulation reaction proceeds via the domino Michael addition/hemiacetalization/intramolecular addition of an enolate to a nitro group/decarbonylation/oxidative aromatization sequence under transition metal-free conditions without the use of an external reductant and oxidant. The synthetic utility of this protocol has been also demonstrated by evaluating the photophysical properties of the synthesized 3-naphthylindole and 3-naphthylbenzo[g]indole derivatives.
      PubDate: 2017-03-16T06:01:18.498425-05:
      DOI: 10.1002/adsc.201601327
  • Transition Metal-Free Iodosobenzene-Promoted Direct Oxidative 3-Arylation
           of Quinoxalin-2(H)-ones with Arylhydrazines
    • Authors: Sanjay Paul; Ji Hyeon Ha, Ga Eul Park, Yong Rok Lee
      Abstract: A transition metal-free iodosobenzene-promoted direct oxidative 3-arylation of quinoxalin-2(H)-ones was developed using various arylhydrazines under air. The protocol affords a variety of 3-arylquinoxalin-2(H)-one derivatives in moderate to good yields. This method provides a rapid access to biologically interesting benzo[g]quinoxalinones and pyrido[3,4-b]pyrazinones. The present methodology features high functional group tolerance including base-sensitive groups as well as allyl- and benzyl-substituted quinoxalin-2(H)-ones under mild reaction conditions.
      PubDate: 2017-03-16T06:01:01.234973-05:
      DOI: 10.1002/adsc.201700070
  • Synthesis of Fluoromethyl-Substituted Isoxazolines via Transition
           Metal-Free Oxyfluorination of Alkenyl Oximes
    • Authors: Juan Zhao; Min Jiang, Jin-Tao Liu
      Abstract: A mild and efficient transition metal-free intramolecular oxyfluorination of alkenyl oximes is demonstrated. The reaction tolerates a range of substrates to give a series of monofluoromethylated isoxazoline derivatives with good yields. The possible pathways are proposed based on the reaction results and control experiments.
      PubDate: 2017-03-16T06:00:44.001145-05:
      DOI: 10.1002/adsc.201601405
  • (Pentamethylcyclopentadienyl)cobalt(III)-Catalyzed C–H Bond
           Functionalization: From Discovery to Unique Reactivity and Selectivity
    • Authors: Tatsuhiko Yoshino; Shigeki Matsunaga
      Abstract: High-valent (pentamethylcyclopentadienyl)cobalt(III) [Cp*Co(III)] catalysts were found as inexpensive alternatives to (pentamethylcyclopentadienyl)rhodium(III) [Cp*Rh(III)] catalysts in the field of C—H bond functionalization, and applied to a variety of transformations. In this review, after the discovery and early examples of Cp*Co(III)-catalyzed C—H bond functionalization are summarized, the unique reactivity and selectivity of Cp*Co(III) and the differences between the cobalt and rhodium catalysis are intensively discussed. Such differences are assumed to be caused by the lower electronegativity, hard nature, and smaller ionic radius of cobalt.
      PubDate: 2017-03-16T05:41:16.300242-05:
      DOI: 10.1002/adsc.201700042
  • Access to Fluorescent Azines from N-Heterocyclic Carbene Precursors and
    • Authors: Siping Wei; Shuangxun Li, Changyou Chen, Zhonghong He, Xi Du, Li Wang, Chun Zhang, Qin Wang
      Abstract: A efficient synthesis of azines from the reaction of N-heterocyclic carbene precursors with N-tosylhydrazones has been developed. This method avoids the direct use of diazo compounds and allows the synthesis of structurally diverse azines. An azine is further found to exhibit strong yellow fluorescence and shows promise as a reagent for biological imaging.
      PubDate: 2017-03-16T03:55:55.552991-05:
      DOI: 10.1002/adsc.201700241
  • Palladium-Catalyzed Dearomatizing Alkoxydiarylation of Furan Rings by
           Coupling with Arylboronic Acids: Access to Polysubstituted Oxabicyclic
    • Authors: Jiuyi Li; Lin Lu, Qi Pan, Bo Liu, Yanwei Ren, Biaolin Yin
      Abstract: We report a protocol for palladium-catalyzed dearomatizing alkoxydiarylation of furan rings via aerobic oxidative coupling between arylboronic acids and 5-aryl-2-hydroxyalkylfurans. This green protocol starting from furan derivatives, which can be sustainably sourced, provides rapid access to polysubstituted 2,3,3a,6a-tetrahydrofuro[3,2-b]furans and hexahydrofuro[3,2-b]furans, oxabicyclic frameworks that are shared by various natural products and synthetic molecules with important biological activities.
      PubDate: 2017-03-16T03:55:47.64298-05:0
      DOI: 10.1002/adsc.201601437
  • (Pentamethylcyclopentadienyl)cobalt(III)-Catalyzed Direct
           Trifluoromethylthiolation of Arenes via C−H Activation
    • Authors: Xu-Ge Liu; Qingjiang Li, Honggen Wang
      Abstract: The direct trifluoromethylthiolation of arenes was realized via (pentamethylcyclopentadienyl)cobalt(III)-catalyzed C(sp2)-H activation and coupling with AgSCF3 under the assistance of a directing group. The reaction features redox-neutrality, mild conditions, broad substrate scope, and good functional group tolerance. Preliminary mechanistic studies have been conducted.
      PubDate: 2017-03-15T09:41:26.326567-05:
      DOI: 10.1002/adsc.201700066
  • Synthesis and properties of 5,7-disubstituted
    • Authors: Lars Ohlendorf; John E. Diaz Velandia, Krisztina Kónya, Peter Ehlers, Alexander Villinger, Peter Langer
      Abstract: A new and efficient two-step procedure for the preparation of 5,7-disubstituted 5,7-dihydropyrido[2,3-b:6,5-b′]diindoles, containing aryl-, benzyl- as well as alkyl-substituents has been developed. This methodology consists of a chemo-selective double Suzuki-Miyaura cross-coupling reaction followed by a fourfold Buchwald-Hartwig amination reaction. UV/VIS absorption and fluorescence measurements have been carried out for a selected series of compounds. The results are summarized and compared with those of the isomeric 5,7-disubstituted 5-7-dihydropyrido[3,2-b:5,6-b′]diindoles.
      PubDate: 2017-03-15T09:35:30.755641-05:
      DOI: 10.1002/adsc.201601390
  • Biocatalytic Approaches towards the Synthesis of Chiral Amino Alcohols
           from Lysine: Cascade Reactions Combining alpha-Keto Acid Oxygenase
           Hydroxylation with Pyridoxal Phosphate- Dependent Decarboxylation
    • Authors: Damien Baud; Olivier Peruch, Pierre-Loïc Saaidi, Aurélie Fossey, Aline Mariage, Jean-Louis Petit, Marcel Salanoubat, Carine Vergne-Vaxelaire, Véronique de Berardinis, Anne Zaparucha
      Abstract: Amino alcohols are a very common structural motif in natural and synthetic molecules. Starting from l-lysine and hydroxy-l-lysine, a straightforward biocatalytic synthesis of beta- and gamma-amino alcohols is presented. Diastereoselective C–H oxidation catalyzed by an alpha-keto acid-dependent oxygenase followed by cleavage of the carboxylic acid moiety of the corresponding chiral hydroxy amino acid by a pyridoxal phosphate-dependent decarboxylase enabled the formation of the target amino alcohols with moderate to complete conversions. Four beta- and gamma-amino alcohols were obtained on a small scale in excellent yields and stereoselectivities.
      PubDate: 2017-03-15T07:50:35.642912-05:
      DOI: 10.1002/adsc.201600934
  • Controlled Reactivity of 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU) in the
           Selective Synthesis of 1-(Bromoethynyl)arenes
    • Authors: Shiva Krishna Moodapelly; Gangavaram V. M. Sharma, Venkata Ramana Doddi
      Abstract: The nucleophilic reactivity of 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) was completely controlled by the formation of monohydrate (DBU⋅H2O) in the synthesis of 1-(bromoethynyl)arenes from 1,1-dibromoalkenes. Differential reactivity of DBU in protic solvents as compared to aprotic solvents has been explored to prevent the formation of mixtures of products in this reaction. Hydrated DBU is found to be superior to dry DBU, both for the selective synthesis and ease of isolation. In addition, use of DBU⋅H2O as a non-nucleophilic mild base allowed us to synthesise 1-(bromoethynyl)arenes via a reaction under solvent-free conditions. Utilization of DBU⋅H2O as sole reagent also allowed us to isolate the products without column chromatographic purifications.
      PubDate: 2017-03-15T07:45:54.968017-05:
      DOI: 10.1002/adsc.201601279
  • Auto-Tandem Catalysis-Induced Synthesis of Trisubstituted Furans through
           Domino Acid-Acid-Catalyzed Reaction of Aliphatic Aldehydes and
           1,3-Dicarbonyl Compounds by using N-Bromosuccinimide as Oxidant
    • Authors: Wenbo Huang; Changhui Liu, Yanlong Gu
      Abstract: A simple aluminium(III) chloride-catalyzed synthesis of tri-substituted furans from aliphatic aldehydes and 1,3-dicarbonyl compounds was developed by using N-bromosuccinimide (NBS) as an oxidant. This method was effective for the synthesis of various furan derivatives. Some of the products were not accessible with the previously reported methods. Mechanically, this reaction involved an auto-tandem catalysis based on a newly reported acid-acid-catalyzed tandem reaction to ensure that furans were successfully synthesized.
      PubDate: 2017-03-15T07:35:40.592844-05:
      DOI: 10.1002/adsc.201700074
  • Synthesis of Chiral-Bridged Atropisomeric Monophosphine Ligands with
           Tunable Dihedral Angles and their Applications in Asymmetric
           Suzuki–Miyaura Coupling Reactions
    • Authors: Wang Xia; Yongsu Li, Zihong Zhou, Huixuan Chen, Hao Liang, Sifan Yu, Xuefeng He, Yaqi Zhang, Jiyan Pang, Zhongyuan Zhou, Liqin Qiu
      Abstract: Precise chiral recognition was firstly realized in the construction of diastereomeric biaryl monophosphines by means of the substrate-directed asymmetric annulation reactions. A series of new chiral-bridged atropisomeric biphenyl monophosphine ligands with tunable dihedral angles was accordingly synthesized successfully without a resolution step being needed. Using these ligands, different kinds of axially chiral 1,1′-biaryl-2-phosphonates including the first reported quinolyl biaryl phosphonates were prepared in 42–97% yields with up to 96% ee via palladium-catalyzed asymmetric Suzuki coupling reactions.
      PubDate: 2017-03-15T07:35:36.670896-05:
      DOI: 10.1002/adsc.201700020
  • Copper(II) Acetate-Catalyzed Hydroxysulfenylation-Initiated Lactonization
           of Unsaturated Carboxylic Acids with Oxygen as Oxidant and Oxygenation
    • Authors: Bingnan Du; Yang Wang, Haibo Mei, Jianlin Han, Yi Pan
      Abstract: A copper(II) acetate-catalyzed aerobic thiolation of C=C double bonds, oxygenation, and intramolecular cyclization reactions of unsaturated carboxylic acids with thiols has been explored. The reaction proceeds through a new hydroxysulfenylation-initiated lactonization pathway with carboxyl as electrophilic group, which provides an efficient access to assembly highly valuable thio-substituted lactone derivatives with good yields under mild conditions. Several control experiments, as well as an isotope labelling experiment disclose that oxygen acts as both oxidant and reactant being transferred into the final product. The mechanistic studies support the discovery of a new strategy through difunctionalization of alkenes based on unsaturated carboxylic acids to construct the diversely substituted lactones.
      PubDate: 2017-03-15T07:35:32.550375-05:
      DOI: 10.1002/adsc.201700036
  • Green and Practical Oxidative Deoximation of Oximes to Ketones or
           Aldehydes with Hydrogen Peroxide/Air by Organoselenium Catalysis
    • Authors: Xiaobi Jing; Dandan Yuan, Lei Yu
      Abstract: Organoselenium-catalyzed oxidative deoximations afforded ketones and aldehydes under mild conditions. The reactions employ hydrogen peroxide and air as clean oxidants and lead to a waste-free and metal-free deprotection protocol for carbonyl protection strategies as well as the green synthesis of ketones and aldehydes. The mechanisms of this interesting organoselenium-catalyzed reaction have been investigated by control experiments as well as the selenium 77 nuclear magnetic resonance (77Se NMR) tests. This novel reaction largely expands the application scope of organoselenium catalysis.
      PubDate: 2017-03-15T07:35:28.273292-05:
      DOI: 10.1002/adsc.201601353
  • Iridium-Catalyzed Enantioselective Hydrogenation of Vinylsilanes
    • Authors: Aie Wang; Maurizio Bernasconi, Andreas Pfaltz
      Abstract: We have screened a diverse array of iridium complexes derived from chiral N,P ligands as catalysts for the asymmetric hydrogenation of vinylsilanes, a transformation for which generally applicable catalysts were lacking. Several catalysts emerged from this study that enabled the highly enantioselective hydrogenation of a wide range of vinylsilanes with trisubstituted or disubstituted terminal C=C bonds bearing aryl, alkyl, ethoxycarbonyl, or hydroxymethyl substituents. In addition to trimethylsilyl and dimethyl(phenyl)silyl derivatives, trialkoxysilyl- and silacyclobutyl-substituted alkenes were used as substrates.
      PubDate: 2017-03-15T07:30:37.736451-05:
      DOI: 10.1002/adsc.201700162
  • On the Gold-Catalyzed Generation of Phenyl Cations from 1,5-Diynes
    • Authors: Thomas Wurm; Janina Bucher, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi
      Abstract: cis-Enediyne systems bearing two non-terminal alkyne functionalities were transformed in the presence of a gold catalyst. A selective 6-endo-dig-cyclization generates mono-aurated phenyl cation intermediates, high energy species that are able to activate even primary sp3-C–H-bonds. Via insertion into intramolecularly offered, unactivated C–H-bonds, penta-substituted benzene derivatives are obtained as final products. In most cases selective insertions into the γ-sp3-C—H bonds of the offered tethers were observed.
      PubDate: 2017-03-15T07:30:31.549125-05:
      DOI: 10.1002/adsc.201700231
  • Asymmetric Strecker reactions catalyzed by thiourea phosphonium and
           ammonium salts
    • Authors: Hongyu Wang; Kaiye Wang, Yanfei Ren, Na Li, Bo Tang, Gang Zhao
      Abstract: The application of asymmetric phase-transfer catalysis to the Strecker reaction of ketimines was realized utilizing bifunctional thiourea-phosphonium salts. The asymmetric Strecker reaction of aldimines was also realized utilizing quaternary ammonium salts derived from amino acids.
      PubDate: 2017-03-13T03:36:55.489765-05:
      DOI: 10.1002/adsc.201700029
  • A Polystyrene-Supported Phase-Transfer Catalyst for Asymmetric Michael
           Addition of Glycine-Derived Imines to α,β-Unsaturated Ketones
    • Authors: Javier Miguélez; Hiroyuki Miyamura, Shū Kobayashi
      Abstract: A 2-oxopyrimidinium salt was immobilized onto a polystyrene-derived polymer to generate a heterogeneous catalyst that effectively promoted the asymmetric Michael addition of glycine-derived imines to α,β-unsaturated ketones. The reactions proceeded smoothly to afford the desired adducts, (S)-tert-butyl 2-[(diarylmethylidene)amino]-5-oxoalkanoates, in high yields and with high enantioselectivities (up to 92% ee). The polymer catalyst could be recovered and reused at least five times without significant loss of activity or selectivity.
      PubDate: 2017-03-13T03:36:50.620841-05:
      DOI: 10.1002/adsc.201700155
  • Diastereoselective Synthesis of Functionalized Angularly-Fused Tetracycles
           via an Organocatalytic Quadruple Reaction Sequence
    • Authors: Fu-Jie Chang; Ramani Gurubrahamam, Kwunmin Chen
      Abstract: An efficient diastereoselective strategy to access complex structural tetracycles was described through an organocascade quadruple reaction sequence between (E)-2-(3-arylallylidene)-1H-indene-1,3(2H)-diones and β-keto esters. The reaction proceeded through remote 1,6-addition followed by sequential 1,4-addition and aldol/aldol reactions to generate angularly-fused carbocyclic motifs with favourable to excellent yields (up to 94%) and diastereoselectivities (up to >20:1 dr). An enantioselective organocascade approach was attempted to yield densely functionalized tetracycles containing seven chiral centres including a quaternary centre.
      PubDate: 2017-03-13T03:36:33.445097-05:
      DOI: 10.1002/adsc.201700023
  • Synthesis of 2-Substituted Quinolines via Rhodium(III)-Catalyzed C−H
           Activation of Imidamides and Coupling with Cyclopropanols
    • Authors: Xukai Zhou; Zisong Qi, Songjie Yu, Lingheng Kong, Yang Li, Wan-Fa Tian, Xingwei Li
      Abstract: The front cover picture, provided by Xingwei Li and co-workers, illustrates an efficient synthesis of 2-substituted quinolines from readily available cyclopropanols and imidamides, which has been developed with the cyclopropanol acting as a C3 synthon. With the assistance of a bifunctional imidamide directing group, the reaction occurred via sequential C−H/C−C cleavage and C−C/C−N bond formation. Details can be found in the communication on pages XXXX–XXXX (X. Zhou, Z. Qi, S. Yu, L. Kong, Y. Li, W.-F. Tian, X. Li, Adv. Synth. Catal. 2017, 359, XXXX–XXXX;
      DOI : 10.1002/adsc.201601278).
      PubDate: 2017-03-08T08:20:30.380455-05:
  • Silver-Based Radical Reactions: Development and Insights
    • Authors: Guichun Fang; Xuefeng Cong, Giuseppe Zanoni, Liu Qun, Xihe Bi
      Abstract: The front cover image, provided by Xihe Bi, illustrates the comprehensive and critical review of silver-based radical reactions, which especially emphasizes reactivity, selectivity and mechanism. The material is organized according to the type of radicals generated in situ, including carbon-centered radicals and heteroatom-centered radicals, such as nitrogen, oxygen, phosphorus, and sulfur radicals. In each section the authors present the radical generation and their use in organic synthesis through oxidation, addition, coupling, radical cascades, etc. The detailed comparison and analysis allow an understanding of the role and catalytic cycle of silver salts in triggering and promoting the radical reactions, which should stimulate further research interest in the field. Details can be found in the review on pages xxxx–xxxx (G. Fang, X. Cong, G. Zanoni, Q. Liu, X. Bi, Adv. Synth. Catal. 2017, 359, xxxx–xxxx;
      DOI 10.1002/adsc.201601179).
      PubDate: 2017-03-07T09:26:01.038556-05:
  • Synthesis of Quinoline N-Oxides by Cobalt-Catalyzed Annulation of
           Arylnitrones and Alkynes
    • Authors: Yue Liu; Chen Wang, Ningning Lv, Zhanxiang Liu, Yuhong Zhang
      Abstract: A new and straightforward protocol for the synthesis of quinoline N-oxides from the annulation of arylnitrones and alkynes is described. For the first time, a [4+2] cyclization of nitrone and alkynes has been achieved by cobalt catalysis via a nitrone-assisted dual C–H cleavage under relatively mild conditions.
      PubDate: 2017-03-07T07:30:55.509602-05:
      DOI: 10.1002/adsc.201600834
  • Tunable Cinchona-Based Thioureas-Catalysed Asymmetric Epoxidation to
           Synthetically Important Glycidic Ester Derivatives
    • Authors: Sara Meninno; Luca Zullo, Jacob Overgaard, Alessandra Lattanzi
      Abstract: A novel class of synthetically important glycidic esters has been obtained via an asymmetric epoxidation of trans-α-cyano-α,β-unsaturated esters catalysed by a multifunctional Cinchona alkaloid-derived thiourea/tert-butyl hydroperoxide (TBHP) system. The glycidic esters, isolated in excellent yield with complete trans-diastereocontrol and high enantioselectivity, proved to be versatile building blocks to access challenging small targets bearing a quaternary stereocenter.
      PubDate: 2017-03-07T07:30:52.696015-05:
      DOI: 10.1002/adsc.201700146
  • Palladium-Catalyzed Cyclization of Free Hydroxyalkenoic Acids: Regio- and
           Chemoselective Access to Methylene Lactones
    • Authors: Yelena Mostinski; Ramesh Kotikalapudi, Viviana Valerio, Riva Nataf, Dmitry Tsvelikhovsky
      Abstract: A general and collective synthesis of medium-sized methylene lactones via controlled cyclizations of easily accessible collective precursors is described. The rapid composition of key–hydroxyalkenoic acid scaffold yields an assembly of oxocanones, oxepanones, and pyranones in a regioselective and stereodirected fashion via palladium-catalyzed cyclization.
      PubDate: 2017-03-07T07:25:39.839697-05:
      DOI: 10.1002/adsc.201601346
  • Vicinal Difunctionalization of Alkenes under Iodine(III) Catalysis
           involving Lewis Base Adducts
    • Authors: Kristina Aertker; Raquel J. Rama, Julita Opalach, Kilian Muñiz
      Abstract: The influence of a 2-pyridinyl substituent on the catalytic performance of aryl iodides as catalyst in iodine(III) chemistry was explored. An efficient Lewis base adduct between the pyridine nitrogen and the electrophilic iodine(III) center was identified and confirmed by X-ray analysis. This arrangement was shown to generate a kinetically competent superior catalyst structure for the catalytic dioxygenation of alkenes. It introduces the concept of Lewis base adduct formation as a kinetic factor in iodine(I/III) catalysis.
      PubDate: 2017-03-07T07:25:36.669032-05:
      DOI: 10.1002/adsc.201601178
  • Direct Reductive Amination of Aldehydes via Environmentally Benign
           Bentonite-Gold Nanohybrid Catalysis
    • Authors: R. J. Maya; Susanna Poulose, Jubi John, R. Luxmi Varma
      Abstract: An efficient, green and reliable method for the direct reductive amination of aldehydes was developed using an environmentally benign bentonite-gold nanohybrid catalyst. Use of this heterogeneous catalyst affords a variety of secondary amines in excellent yield under ambient reaction conditions in the presence of phenyldimethylsilane as mild hydride donor. The catalyst is recyclable, selective and is well applicable for the gram-scale preparation of secondary amines.
      PubDate: 2017-03-07T07:25:33.779903-05:
      DOI: 10.1002/adsc.201601042
  • Chemoselective, Isomerization-Free Synthesis of N-Acylketimines from
           N–H Imines
    • Authors: Yearang Kwon; Young Ho Rhee, Jaiwook Park
      Abstract: N-Acylketimines were synthesized through a ruthenium-catalyzed generation of N–H ketimines from secondary azides and subsequent acylation with mixed anhydrides under mild conditions. The synthetic scope was broad to give N-acylimines having various functional groups, including those with aliphatic groups that are prone to tautomerization to the corresponding enamides. In addition, various acyl moieties were accommodated. The synthetic utility of this chemoselective imine generation was illustrated by a highly diastereoselective nucleophilic addition of a Grignard reagent to a cyclic N-acylimine.
      PubDate: 2017-03-07T07:25:31.024473-05:
      DOI: 10.1002/adsc.201601406
  • Hydroxynitrile Lyase Isozymes from Prunus communis: Identification,
           Characterization and Synthetic Applications
    • Authors: Yu-Cong Zheng; Jian-He Xu, Hui Wang, Guo-Qiang Lin, Ran Hong, Hui-Lei Yu
      Abstract: Biocatalysts originating from Badamu (Prunus communis) have been applied to catalyze the asymmetric synthesis of (R)-4-methylsulfanylmandelonitrile, a key building block of thiamphenicol and florfenicol. Here, four hydroxynitrile lyase (HNL) isozymes from Badamu were cloned and heterologously expressed in Pichia pastoris. The biochemical properties and catalytic performances of these isozymes were comprehensively explored to evaluate their efficiency and selectivity in asymmetric synthesis. Among then, PcHNL5 was identified with outstanding activity and enantioselectivity in asymmetric hydrocyanation. Under the optimized mild biphasic reaction conditions, seventeen prochiral aromatic aldehydes were converted to valuable chiral cyanohydrins with good yields (up to 94%) and excellent optical purities (up to >99.9% ee), which provide a facile access to numerous chiral amino alcohols, hypoglycemic agents, angiotension converting enzyme (ACE) inhibitors and β-blockers. This work therefore underlines the importance of discovering the most potent biocatalyst among a group of isozymes for converting unnatural substrates into value-added products.
      PubDate: 2017-03-07T07:25:28.898114-05:
      DOI: 10.1002/adsc.201601332
  • Biocatalytic Approach to Enantioenriched β-Hydroxydioxinones using
    • Authors: Rick C. Betori; Eric R. Miller, Karl A. Scheidt
      Abstract: The front cover picture, provided by Karl Scheidt and co-workers, illustrates the development of a biocatalytic reduction of β-ketodioxinones to form highly enantioenriched β-hydroxydioxinones. This practical system provides a high yielding solution to access a broad class of β-hydroxydioxinones that are of great interest due to their diversification capabilities. Details can be found in the communication on pages XXXX–XXXX (R. C. Betori, E. R. Miller, K. A. Scheidt, Adv. Synth. Catal. 2017, 359, XXXX–XXXX;
      DOI : 10.1002/adsc.201700095).
      PubDate: 2017-03-03T04:10:26.544859-05:
  • Phosphine-Mediated Dimerization of Conjugated Ene-Yne Ketones:
           Stereoselective Construction of Dihydrobenzofurans
    • Authors: Cheng-Zhi Zhu; Yao-Liang Sun, Yin Wei, Min Shi
      Abstract: A new strategy for the phosphine-mediated dimerization of conjugated ene-yne ketones to produce functionalized dihydrobenzofurans has been developed, affording diversified 4,5-dihydrobenzofurans in moderate to excellent yields with high diastereoselectivities under mild conditions. This new synthetic method can tolerate a variety of functional groups and can be performed on a gram scale and in an asymmetric variant using the chiral phosphine Xyl-BINAP to give the desired products with up to 94% ee.
      PubDate: 2017-03-02T07:50:37.494948-05:
      DOI: 10.1002/adsc.201700031
  • Recent Advances in Organic Reactions Involving Elemental Sulfur
    • Authors: Thanh Binh Nguyen
      Abstract: Elemental sulfur has been known since Antiquity and found widespread applications in the preparation of black gunpowder, the synthesis of sulfuric acid as well as other sulfur-containing compounds, and the vulcanization of rubber. Over the last several years, we have come to better understand its properties and discover more applications of elemental sulfur in synthetic organic chemistry. This review summarizes the advances from 2000 in the construction of organic molecules using elemental sulfur via sulfuration, oxidation, reduction and redox condensation processes.
      PubDate: 2017-03-02T07:41:24.943682-05:
      DOI: 10.1002/adsc.201601329
  • Enantioselective Chloro-O-cyclization of Unsaturated N-Tosylcarbamates
    • Authors: Hui Yang; Guo-Tao Fan, Ling Zhou, Jie Chen
      Abstract: An enantioselective chloro-O-cyclization of unsaturated N-tosylcarbamates has been developed for the first time using a Cinchona-derived quaternary ammonium salt as the catalyst, the desired enantioenriched chloromethyldioxolanimines were prepared with excellent regioselectivities and high enantioselectivities.
      PubDate: 2017-03-02T07:35:29.300673-05:
      DOI: 10.1002/adsc.201601328
  • A Biocatalytic Route to Highly Enantioenriched β-Hydroxydioxinones
    • Authors: Rick C. Betori; Eric R. Miller, Karl A. Scheidt
      Abstract: A novel biocatalytic system to access a wide variety of β-hydroxydioxinones from β-ketodioxinones employing commercial engineered ketoreductases has been developed. This practical system provides a remarkably straightforward solution to limitations in accessing certain chemical scaffolds common in β-hydroxydioxinones that are of great interest due to their diversification capabilities. A few highlights of this system are that it is high yielding, highly enantioselective, and chromatography-free. We have demonstrated both a wide substrate scope and a high degree of scalability.
      PubDate: 2017-03-02T04:40:31.358704-05:
      DOI: 10.1002/adsc.201700095
  • Synthesis of 3-Aryl-2-(trifluoromethyl)indoles via Copper-Catalyzed
           Hydroarylation and Subsequent Cadogan Cyclization
    • Authors: Yoshishiko Yamamoto; Erina Ohkubo, Masatoshi Shibuya
      Abstract: The copper-catalyzed hydroarylation of (trifluoromethyl)alkynes with (o-nitrophenyl)boronic acids selectively afforded trisubstituted (trifluoromethyl)alkenes bearing an o-nitrophenyl group. The obtained hydroarylation products were converted into 3-aryl-2-(trifluoromethyl)indoles in high yields via molybdenum-catalyzed Cadogan cyclization. Similarly, the hydroarylation product prepared from (o-nitrophenyl)(trifluoromethyl)alkyne and (p-anisyl)boronic acid also underwent Cadogan cyclization, albeit with a longer reaction time, affording the desired indole product in a high yield.
      PubDate: 2017-02-28T03:21:41.751027-05:
      DOI: 10.1002/adsc.201700122
  • Inter- and Intramolecular Cyclopropanations of Diazo Weinreb Amides
           Catalyzed by Ruthenium(II)-Amm-Pheox
    • Authors: Hamada S. A. Mandour; Soda Chanthamath, Kazutaka Shibatomi, Seiji Iwasa
      Abstract: Inter- and intramolecular cyclopropanations of a series of diazo Weinreb amides and trans-allylic diazo Weinreb amide derivatives have been achieved using chiral ruthenium(II)-Amm-Pheox catalyst to give the corresponding chiral cyclopropyl Weinreb amides in excellent yield (up to 99%) with excellent enantioselectivity (up to 99% ee). The chiral products could easily undergo useful synthetic transformations to give the corresponding aldehydes, alcohols and ketones in high yields and enantioselectivities.
      PubDate: 2017-02-28T03:21:21.579325-05:
      DOI: 10.1002/adsc.201601345
  • Copper-Catalyzed Asymmetric Allylic Alkylation of β-Keto Esters with
           Allylic Alcohols
    • Authors: Paz Trillo; Alejandro Baeza
      Abstract: The asymmetric allylic alkylation reaction of β-keto esters catalyzed by copper complex tBuBOX-Cu(OTf)2 employing allylic alcohols as environmentally friendly electrophilic partner, is herein described. This new protocol renders in general the corresponding allylic products with two consecutive all-carbon stereocenters in good both yields and enantioselectivities and with low to modest diastereoselection. The regioselectivity of the process seems to be governed by the formation of the most stable olefin according to the results obtained when non-symmetrically substituted alcohols were employed. The scope, limitations and mechanistic aspects of the process are also discussed.
      PubDate: 2017-02-24T02:55:28.282915-05:
      DOI: 10.1002/adsc.201601139
  • Chelation-Assisted Palladium-Catalyzed γ-Arylation of Aliphatic
           Carboxylic Acid Derivatives
    • Authors: Aniruddha Dey; Sandeep Pimparkar, Arghya Deb, Srimanta Guin, Debabrata Maiti
      Abstract: A palladium(II)-catalyzed protocol for the highly regioselective remote γ-C–H arylation of aliphatic carboxylic acid has been disclosed. The 8-aminoquinoline moiety as an intramolecular bidentate chelator was found to be suitable for this γ-C–H arylation. Various aryl iodides successfully produced the regioselectively mono-arylated products with negligible diarylation. Functional group tolerance and easy-to-handle reaction conditions make this method attractive.
      PubDate: 2017-02-23T05:30:40.827925-05:
      DOI: 10.1002/adsc.201601121
  • Visible-Light Photoredox-Catalyzed Aminosulfonylation of Diaryliodonium
           Salts with Sulfur Dioxide and Hydrazines
    • Authors: Nai-Wei Liu; Shuai Liang, Georg Manolikakes
      Abstract: A photoredox-catalyzed three-component synthesis of N-aminosulfonamides starting from diaryliodonium salts, hydrazines and sulfur dioxide is reported. This reaction proceeds under mild conditions at room temperature and is driven by visible light. A simple bisulfite salt can be used as a readily available and easy-to-handle sulfur dioxide source. Mechanistic studies support a catalytic photoredox pathway with the diaryliodonium salt as convenient source for aryl radicals.
      PubDate: 2017-02-23T05:30:36.979458-05:
      DOI: 10.1002/adsc.201601341
  • Olefin-Migrative Cleavage of Cyclopropane Rings through the
           Nickel-Catalyzed Hydrocyanation of Allenes and Alkenes
    • Authors: Hiroto Hori; Shigeru Arai, Atsushi Nishida
      Abstract: A nickel-catalyzed hydrocyanation triggered by hydronickelation of the carbon-carbon double bonds of allenes followed by cyclopropane cleavage is described. The observed regio- and stereochemistries in the products are strongly influenced by the initial hydronickelation step, and allenyl- and methylenecyclopropanes reacted smoothly to promote the cleavage of cyclopropane. In contrast, this cleavage was not observed with vinylidenecyclopropanes, because the initial hydronickelation does not give a suitable intermediate for cleavage of the cyclopropanes.
      PubDate: 2017-02-23T05:30:27.139895-05:
      DOI: 10.1002/adsc.201601400
  • A Method to Access Symmetrical Tetrasubstituted Pyridines via Iodine and
           Ammonium Persulfate Mediated [2+2+1+1]-Cycloaddition Reaction
    • Authors: Weibing Liu; Hua Tan, Cui Chen, Yupeng Pan
      Abstract: A novel metal-free [2+2+1+1]-cycloaddition method for rapid and productive preparation of symmetrical 2,3,5,6-tetrasubstituted pyridines has been developed from α-substituted arones and N,N-dimethyl formamide (DMF) using iodine (I2) and ammonium persulfate ((NH4)2S2O8) as mediators. In this process, both DMF and (NH4)2S2O8 play a dual role for the formation of pyridines. DMF acts as the reaction medium and the C4 source (the methyl group of DMF), while (NH4)2S2O8 serves as the oxidant and nitrogen resource. Notably, this transformation exhibited a broad substrate scope towards a wide variety of different arones to give the corresponding tetrasubstituted pyridines in moderate to excellent yields.
      PubDate: 2017-02-22T08:50:27.583757-05:
      DOI: 10.1002/adsc.201601225
  • Intramolecular Carbonylative C–H Functionalization of 1,2,3- Triazoles
           for the Synthesis of Triazolo[1,5-a]indolones
    • Authors: Cedrick Veryser; Gert Steurs, Luc Van Meervelt, Wim M. De Borggraeve
      Abstract: This study presents a synthesis of 4H-[1,2,3]triazolo[1,5-a]indol-4-ones. The key step in the synthesis of this new heterocyclic scaffold is an intramolecular cyclization via an unprecedented carbonylative C–H functionalization of 1-(2-bromoaryl)-1,2,3-triazoles. Isotopic labelling of the carbonyl carbon atom is possible using near stoichiometric amounts of 13CO. Additionally, an alternative pathway via carbonylative Sonogashira coupling followed by a two-step, one-pot azidation/cycloaddition is also investigated, giving rise to the same scaffold.
      PubDate: 2017-02-21T06:56:24.825267-05:
      DOI: 10.1002/adsc.201601388
  • Direct Access to Isoindolin-1-one Scaffolds by Copper-Catalyzed Divergent
           Cyclizations of 2-Formylbenzonitrile and Diaryliodonium Salts
    • Authors: Li Liu; Jian Qiang, Shu-Hua Bai, Hui-Ling Sung, Chun-Bao Miao, Jian Li
      Abstract: Copper-catalyzed cascade transformations of 2-formylbenzonitrile and diaryliodonium salts were carried out to efficiently afford isoindolin-1-one scaffolds. The process proceeds through a copper-catalyzed tandem C–H/N–H arylation, producing two different isoindolin-1-one derivatives under different reaction conditions.
      PubDate: 2017-02-21T06:56:18.727409-05:
      DOI: 10.1002/adsc.201601403
  • Base-Promoted Addition of Arylacetonitriles to Terminal Alkynes: Regio-
           and Stereoselective Access to Disubstituted Acrylonitriles
    • Authors: Chaorong Qi; Youbin Peng, Lu Ouyang, Yanwei Ren, Huanfeng Jiang
      Abstract: A base-promoted nucleophilic addition of arylacetonitriles to terminal alkynes has been described for the first time, providing a simple and straightforward protocol for the synthesis of a range of structurally diverse (Z)-2,3-disubstituted acrylonitriles in moderate to excellent yields. Of particular note, the transition metal-free carbon-carbon double bond forming reaction is regio- and stereoselective under mild conditions. A variety of functional groups can be tolerated on both the arylacetonitrile substrate and the alkyne coupling partner. Moreover, the reaction is easily scalable and the products thus obtained can serve as versatile intermediates for the synthesis of a series of useful substances.
      PubDate: 2017-02-21T06:56:15.808545-05:
      DOI: 10.1002/adsc.201601024
  • Late-Stage Diversification of Non-Steroidal Anti-Inflammatory Drugs by
           Transition Metal-Catalyzed C–H Alkenylations, Thiolations and
    • Authors: Wenbo Ma; Hongbo Dong, Daoxin Wang, Lutz Ackermann
      Abstract: The front cover image provided by Wenbo Ma and Lutz Ackermann, illustrates the ruthenium- and silver-catalyzed selective C–H alkenylations, thiolations and selenylations of phenazones with alkenes, disulfides and diselenides. These transformations could be applied to a wide range of substrates and proceed with excellent levels of chemo- and site-selectivity as well as high functional group tolerance. The power of the C–H functionalization strategy was also reflected by late-stage diversification to access selectively substituted pyrazolones with diverse pharmacological activities. Further details can be found in the full paper on page xxxx–xxxx (W. Ma, H. Dong, D. Wang, L. Ackermann, Adv. Synth. Catal. 2017, 359, xxxx–xxxx (
      DOI : 10.1002/adsc.201600937)
      PubDate: 2017-02-21T06:55:58.726858-05:
  • Regio- and Stereospecific O-Glycosylation of Phenolic Compounds Catalyzed
           by a Fungal Glycosyltransferase from Mucor hiemalis
    • Authors: Jin Feng; Peng Zhang, Yinglu Cui, Kai Li, Xue Qiao, Ying-Tao Zhang, Shu-Ming Li, Russell J. Cox, Bian Wu, Min Ye, Wen-Bing Yin
      Abstract: Glycosylated small molecules are often bioactive and obtained mainly via microbial biotransformation especially by fungi. However, no responsible glycosylation gene/enzyme has yet been uncovered in a filamentous fungus. We report here the first identification of a phenolic glycosyltransferase MhGT1 from Mucor hiemalis. The substrate promiscuity of the new phenolic O-glycosyltransferase was explored by using phenols from Traditional Chinese Medicinal herbs as substrates. MhGT1 exhibited robust capabilities for the regio- and stereospecific O-glycosylation of 72 structurally diverse drug-like scaffolds and sterols with uridine diphosphate (UDP) glucose as a sugar donor. Unprecedentedly, MhGT1 showed higher regiospecificities and activities for prenylated phenols than for their non-prenylated analogues. Computational modelling of MhGT1 uncovered a truncated N-terminal domain of the enzyme consisting of hydrophobic and charged amino acid residues which contributed to the broad substrate scope and regiospecificity towards prenylated compounds. Our findings expand the ways to obtain new glycosyltransferases and also effectively apply the enzymatic approach to obtain glycosylated compounds in drug discovery.
      PubDate: 2017-02-16T09:25:37.895016-05:
      DOI: 10.1002/adsc.201601317
  • Efficient Oxidative Coupling of Arenes via Electrochemical Regeneration of
           2,3-Dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) under Mild Reaction
    • Authors: Philipp Röse; Steffen Emge, Christoph Alexander König, Gerhard Hilt
      Abstract: The intramolecular dehydrogenative carbon-carbon bond formation of aromatic rings in the presence of catalytic amounts of an oxidising agent is herein described. The oxidative coupling is realised under indirect anodic conditions, utilising 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ) as an efficient redox mediator under acidic conditions. In comparison, for the stoichiometric oxidative coupling reaction of hexakis(4-tert-butylphenyl)benzene on a 1.0 gram scale, 1.56 g of DDQ were applied, whereas in the present indirect electrochemical version, only 15 mg of DDQ were needed, resulting in significantly easier purifications of the products. The reaction proceeds smoothly using a variety of polyaromatics including terphenyl, quaterphenyl and heptaphenyl derivatives to give polyphenylenes in excellent yields and current efficiencies. A detailed optimisation study, investigations on the electrochemical behaviour of the redox mediator and synthetic applications of the method are discussed.
      PubDate: 2017-02-16T09:25:32.145275-05:
      DOI: 10.1002/adsc.201601331
  • Ferrocenylindium Reagents in Palladium-Catalyzed Cross-Coupling Reactions:
           Asymmetric Synthesis of Planar Chiral 2-Aryl Oxazolyl and Sulfinyl
    • Authors: Mauro Mato; Cristina Pérez-Caaveiro, Luis A. Sarandeses, José Pérez Sestelo
      Abstract: The preparation of ferrocenylindium species and palladium-catalyzed cross-coupling reactions for the synthesis of monosubstituted and planar chiral 1,2-disubstituted ferrocenes is described. Triferrocenylindium reagents (Fc3In) are efficiently prepared in a one-pot procedure from ferrocenes by lithiation and transmetallation to indium using InCl3. The palladium-catalyzed cross-coupling reactions of Fc3In (40 mol%) with a variety of organic electrophiles (aryl, heteroaryl, benzyl, alkenyl and acyl halides) in THF at 80 °C overnight provided a wide variety of monosubstituted ferrocenes in good to excellent yields. This methodology allowed the stereoselective synthesis of planar chiral 2-aryl-1-oxazolylferrocenes and 2-aryl-1-sulfinylferrocenes, which are of interest in asymmetric catalysis.
      PubDate: 2017-02-16T09:20:25.106009-05:
      DOI: 10.1002/adsc.201601397
  • Synthesis of 2-Alkylaminoquinolines and 1,8-Naphthyridines by Successive
    • Authors: Wan Lv; Biao Xiong, Huanfeng Jiang, Min Zhang
      Abstract: A new one-pot synthetic protocol, enabling the facile access to 2-alkylaminoquinolines and 1,8-naphthyridines by successive ruthenium-catalyzed dehydrogenative annulation and N-alkylation processes, has been demonstrated. A series of 2-aminoarylmethanols were efficiently converted in combination with different types of nitriles and alcohols into various desired products in moderate to excellent yields after isolation. Advantageously, the synthesis proceeds with high atom-efficiency, broad substrate scope, operational simplicity, no need for external hydrogen sources and less environmentally benign halogenated reagents, thus offering a practical approach to access these two types of compounds that are currently difficult to prepare with the conventional methods.
      PubDate: 2017-02-15T15:25:41.684891-05:
      DOI: 10.1002/adsc.201601287
  • Host-Catalyzed Cyclodehydration–Rearrangement Cascade Reaction of
           Unsaturated Tertiary Alcohols
    • Authors: Lorenzo Catti; Alexander Pöthig, Konrad Tiefenbacher
      Abstract: The Brønsted acidic resorcin[4]arene hexamer can be applied as an effective catalyst in the dehydrative cyclization and subsequent rearrangement of unsaturated tertiary alcohols. This is the first report on catalyzing such a reaction with a Brønsted acid. Scope and limitations of this cyclopentene-forming reaction sequence are presented. Furthermore, substrate-selective conversion as well as competitive inhibition are described and provide evidence that the reactions proceed within the cavity of the self-assembled structure. Additionally, a cyclobutanone-forming intramolecular hydride transfer of an encapsulated cyclopropyl acetate is reported.
      PubDate: 2017-02-15T15:25:33.213722-05:
      DOI: 10.1002/adsc.201601363
  • Rhodium(III)-Catalyzed Controllable C−H Bond Functionalization of
           Benzamides and Vinylidenecyclopropanes: A Directing Group Determined
           Reaction Pathway
    • Authors: Cheng Ji; Qin Xu, Min Shi
      Abstract: A controllable rhodium(III)-catalyzed C−H bond activation of benzamides and vinylidenecyclopropanes (VDCPs) by changing the directing group from C(O)NH–OPiv to C(O)NH–OBoc has been disclosed, affording two different major products in good yields under mild condition, respectively. The substrate scope has been investigated and a plausible reaction mechanism has been also proposed on the basis of previous literature.
      PubDate: 2017-02-15T15:25:27.978295-05:
      DOI: 10.1002/adsc.201601308
  • Asymmetric Dearomatizative Diels–Alder Reaction for the Construction of
           Hydrodibenzo[b,d]furan Frameworks with Tetrasubstituted Stereogenic
    • Authors: Ben-Xian Xiao; Wei Du, Ying-Chun Chen
      Abstract: Constructing fused hydrodibenzofuran architectures bearing a tetrasubstituted stereogenic center adjacent to an O atom is extremely difficult. Here we have developed an asymmetric dearomatizative Diels–Alder reaction using novel 2-(3-vinylbenzofuran-2-yl)ethan-1-one substrates and 3-olefinic 7-azaoxindoles. The reaction proceeds via in situ generation of a HOMO-raised formal trienamine species with a chiral primary amine catalyst, producing highly complex tetrahydrodibenzo[b,d]furan derivatives with vicinal tetrasubstituted stereogenic centers in moderate yields with excellent stereoselectivity (dr>19:1, up to 98% ee).
      PubDate: 2017-02-15T09:45:27.972491-05:
      DOI: 10.1002/adsc.201601207
  • Efficient Selenium-Catalyzed Selective C(sp3)−H Oxidation of
           Benzylpyridines with Molecular Oxygen
    • Authors: Weiwei Jin; Poonnapa Zheng, Wing-Tak Wong, Ga-Lai Law
      Abstract: An efficient selenium-catalyzed direct oxidation of benzylpyridines in aqueous DMSO has been successfully developed by using molecular oxygen as the oxidant. A variety of benzoylpyridines with broad functional group tolerance were obtained in modest to excellent yields and with exclusive chemoselectivity.
      PubDate: 2017-02-08T08:25:30.112717-05:
      DOI: 10.1002/adsc.201601065
  • Regioselective Direct C3-Phosphorylation of N-Sulfonylindoles under Mild
           Oxidative Conditions
    • Authors: Feng Su; Weidong Lin, Pengfei Zhu, Dezhi He, Jianbin Lin, Hui-Jun Zhang, Ting-Bin Wen
      Abstract: The reactions of N-sulfonylindoles with H-phosphine oxides under oxidative conditions give a wide range of C-3 phosphorylated free (NH)-indoles. Several mild oxidants, such as AgNO3, di-tert-butyl peroxide (DTBP), and K2S2O8, can be used to promote this transformation.
      PubDate: 2017-02-07T08:09:26.191277-05:
      DOI: 10.1002/adsc.201601204
  • Diarylprolinol as a Ligand for Enantioselective Alkynylation of Cyclic
    • Authors: Lode De Munck; Alicia Monleón, Carlos Vila, José R. Pedro
      Abstract: An easily accessible prolinol derived ligand, (S)-bis(3,5-bis(trifluoromethyl)phenyl)(pyrrolidin-2-yl)methanol, has been efficiently applied in the catalytic enantioselective addition of terminal alkynes to cyclic imines using dimethylzinc (Me2Zn) under mild reaction conditions. The developed catalytic system led to chiral propargylic sulfamidates with high yields (up to 97%) and excellent enantioselectivities (up to 97% ee).
      PubDate: 2017-02-07T07:15:29.232027-05:
      DOI: 10.1002/adsc.201601379
  • Green Organocatalytic Synthesis of Indolines and Pyrrolidines from Alkenes
    • Authors: Alexis Theodorou; Christoforos G. Kokotos
      Abstract: Employing a green and efficient 2,2,2-trifluoroacetophenone-catalyzed oxidation of alkenes, which utilizes H2O2 as the green oxidant, a novel and sustainable synthesis of indolines and pyrrolidines was developed. This constitutes a cheap, general and environmentally-friendly protocol for the synthesis of substituted nitrogen-containing heterocycles. A variety of substitution patterns, both aromatic and aliphatic moieties, are well tolerated leading to the desired nitrogen heterocycles in good to excellent yields.
      PubDate: 2017-02-07T07:15:24.545661-05:
      DOI: 10.1002/adsc.201601262
  • Visible Light-Mediated Copper(I)-Catalysed Aerobic Oxidation of
           Ynamides/Ynamines at Room Temperature: A Sustainable Approach to the
           Synthesis of α-Ketoimides/α-Ketoamides
    • Authors: Ayyakkannu Ragupathi; Vaibhav Pramod Charpe, Arunachalam Sagadevan, Kuo Chu Hwang
      Abstract: A novel visible light-mediated, copper-catalysed aerobic oxidation of the C≡C bond in ynamides/ynamines at room temperature by using molecular oxygen as an oxidant is described. Overall, 23 examples were demonstrated with substrates having a wide range of functional groups. The current protocol can be readily scaled up to a preparative (1–2 g) scale with high yields (78–92%), high atom efficiency, and reaction mass efficiency. The mechanistic study shows that in-situ formation of a copper(I)-coordinated π-complex (λmax=460 nm) is most probably the key light absorbing species responsible for the visible light-induced oxidation of ynamides and ynamines. This sustainable oxidation approach allows the direct synthesis of potentially important novel α-ketoimide/α-ketoamide skeletons without the need of external oxidants (organic/inorganic oxidants) and generation of stoichiometric amounts of wastes.
      PubDate: 2017-02-07T05:45:28.232893-05:
      DOI: 10.1002/adsc.201600925
  • One-Pot Assembly of Highly Functionalized Cyclopenta[b]pyrroles via a
           Calcium(II)- and Copper(II)-Catalyzed Reaction Sequence
    • Authors: Lucile Marin; Vincent Gandon, Emmanuelle Schulz, David Lebœuf
      Abstract: A user-friendly, calcium(II)- and copper(II)-catalyzed one-pot reaction sequence to furnish cyclopenta[b]pyrroles with a high level of complexity is depicted. The reaction involves the following sequential transformations: (i) an aza-Piancatelli cyclization, (ii) a hydroamination/isomerization process and (iii) a subsequent Friedel–Crafts-type reaction to afford the desired compounds from readily available 2-furylcarbinols, anilines and secondary alcohols with a minimum of precautions.
      PubDate: 2017-02-07T05:40:28.525516-05:
      DOI: 10.1002/adsc.201601301
  • Palladium-Catalyzed Addition of Arylboronic Acids to para- Quinone
           Methides for Preparation of Diarylacetates
    • Authors: Ruijing Zhuge; Liang Wu, Mao Quan, Nicholas Butt, Guoqiang Yang, Wanbin Zhang
      Abstract: A palladium-catalyzed addition of arylboronic acids to para-quinone methides has been developed. The catalytic system employing 4,4′-dimethoxy-2,2′-bipyridine (DMeO-BPy) as ligand and trifluoroethanol (TFE) as solvent provides diarylacetate products in high yields. A wide range of functionalized arylboronic acids can be used and the method tolerates some variation in the scope of the para-quinone methides.
      PubDate: 2017-02-06T08:35:35.772185-05:
      DOI: 10.1002/adsc.201601302
  • Synthesis of Fluorenes with an All-Carbon Quaternary Center via
           Palladium-Catalyzed Dual Arylation using Cyclic Diaryliodonium Triflates
    • Authors: Xiaopeng Peng; Hongwen Luo, Fuhai Wu, Daqian Zhu, A. Ganesan, Peng Huang, Shijun Wen
      Abstract: Catalyzed by palladium species, cyclic diaryliodonium salts underwent dual C-aryl functionalization smoothly with activated methylene sources. With this new finding, a series of diversified fluorenes with an all-carbon quaternary center was quickly constructed. Moreover, our approach also provided various novel spirofluorenes containing barburate acid or indane motifs which are featured in medicinal drugs and functional materials.
      PubDate: 2017-02-06T08:30:30.454189-05:
      DOI: 10.1002/adsc.201601260
  • Advances in Organocatalytic 1,6-Addition Reactions: Enantioselective
           Construction of Remote Stereogenic Centers
    • Authors: Pankaj Chauhan; Uğur Kaya, Dieter Enders
      Abstract: Due to the competing 1,4-addition reactions and the distance from the chirality information, the construction of a remote stereogenic center via 1,6-addition reactions is often regarded as a great challenge in asymmetric synthesis. Recently, the use of organocatalysts has provided new, excellent alternatives to activate the remote δ-position and facilitate the enantioselective 1,6-addition reactions. In this regard, different new activation modes have been devised and new types of substrates have been employed. This review describes all the recent developments in this area.
      PubDate: 2017-02-06T08:25:43.076429-05:
      DOI: 10.1002/adsc.201601342
  • Regioselective Hydroxylation of Stilbenes by Engineered Cytochrome P450
           from Thermobifida fusca YX
    • Authors: Ansgar Rühlmann; Dragutin Antovic, Thomas J. J. Müller, Vlada B. Urlacher
      Abstract: Since the past decades, the plant stilbenoid resveratrol has gained significant attention of the general public as well as the research community due to its versatile medicinal properties. Apart from resveratrol, there is also an increasing interest in other plant stilbenoids because of their different potential biological activities. In order to meet the increasing demand for stilbenoids, alternative and sustainable approaches for their production are needed. We identified the cytochrome P450 monooxygenase 154E1 from Thermobifida fusca YX (CYP154E1) which enables the synthesis of (E)-4,4′-dihydroxystilbene via direct double hydroxylation of (E)-stilbene. The construction of a triple mutant led to a more than six-fold increased catalytic efficiency compared to the wild type enzyme. CYP154E1 and variants thereof accepted not only (E)-stilbene but also possessed remarkable activity towards ortho- and meta-substituted hydroxystilbenes leading to resveratrol, (E)-2,4′-dihydroxystilbene, (E)-2,4′,5-trihydroxystilbene and (E)-3,4′-dihydroxystilbene. The combination of protein engineering and the use of methyl-β-cyclodextrin as substrate solubilizing agent resulted in product titers of up to 4.2 g L−1 and enzyme total turnover numbers (TTN) of up to 20,000.
      PubDate: 2017-02-06T07:00:26.681641-05:
      DOI: 10.1002/adsc.201601168
  • Cooperative Electrocatalytic and Chemoselective Alcohol Oxidation by
           Shvo's Catalyst
    • Authors: Jeroen Lybaert; Stanislav Trashin, Bert U. W. Maes, Karolien De Wael, Kourosch Abbaspour Tehrani
      Pages: 919 - 925
      Abstract: A new electrocatalytic conversion of alcohols to ketones and aldehydes was developed based on an electrochemical study of Shvo's complex. The oxidation of secondary alcohols was efficiently performed under mild conditions using a catalytic amount of Shvo's catalyst, in combination with a sub-stoichiometric amount of 2,6-dimethoxy-1,4-benzoquinone in N,N-dimethylformamide at 80 °C. The hydroquinone thus formed is continuously reoxidized with the aid of an electrochemical device. Excellent yields for different ketones, aromatic as well as aliphatic and α,β-unsaturated ketones, are obtained. In addition, chemoselectivity towards oxidation of the secondary alcohol is achieved when converting vicinal diols such as 1,2-octanediol and 1,2-decanediol.
      PubDate: 2017-01-26T08:55:27.235987-05:
      DOI: 10.1002/adsc.201600783
  • An Atom-Economical Route to Substituted β-Arylethyl Ketones:
           Phosphomolybdic Acid-Catalyzed Carbohydroxylation of Terminal Alkynes in
           Organic Carbonate
    • Authors: Guo-Ping Yang; Nan Zhang, Nuan-Nuan Ma, Bing Yu, Chang-Wen Hu
      Pages: 926 - 932
      Abstract: A highly efficient and atom-economical route for the synthesis of substituted β-arylethyl ketones was developed by using cheap phosphomolybdic acid (H3PMo12O40) as catalyst and non-volatile propylene carbonate (PC) as green solvent via the carbohydroxylation of terminal alkynes with benzylic alcohols under mild conditions. Various functional groups on the benzylic alcohols and terminal alkynes were tolerated, giving the corresponding substituted β-arylethyl ketones as products in good to excellent yields (up to 95%). It is worth noting that a turnover number (TON) of up to 520 was achieved in the protocol. The mechanism investigation showed that PC might stabilize the heteropoly anion and the carbocation intermediate thus facilitating the carbohydroxylation reaction.
      PubDate: 2017-01-18T05:00:46.977616-05:
      DOI: 10.1002/adsc.201601231
  • “Naked” Iridium(IV) Oxide Nanoparticles as Expedient and Robust
           Catalysts for Hydrogenation of Nitrogen Heterocycles: Remarkable Vicinal
           Substitution Effect and Recyclability
    • Authors: Yi-Gang Ji; Kai Wei, Teng Liu, Lei Wu, Wei-Hua Zhang
      Pages: 933 - 940
      Abstract: Iridium(IV) oxide nanoparticles were facilely prepared from iridium trichloride hydrate and sodium hydroxide by a ball-milling reaction at room temperature. The “naked” iridium nanocatalyst showed high stability and activity for the hydrogenation of a series of nitrogen heterocycles, for the first time, under a hydrogen balloon at room temperature with a selectivity of higher than 99%. Besides, an unprecedented substitution-dependent effect was discovered, where substrates with vicinal substituents on 2-, 3-, or 8-positions exhibited distinctly higher reaction rates than unsubstituted or remote substituted ones. Extraordinary recyclability was discovered in the hydrogenation of 2-methylquinoline for 30 runs without loss of activity.
      PubDate: 2017-01-18T05:01:15.934078-05:
      DOI: 10.1002/adsc.201601370
  • Utilizing an Encapsulated Solution of Reagents to Achieve the
           Four-Component Synthesis of (Benzo)Thiophene Derivatives
    • Authors: Chaoren Shen; Anke Spannenberg, Matthias Auer, Xiao-Feng Wu
      Pages: 941 - 946
      Abstract: Reagent capsules can help to resolve the compatibility problem of reagents in multicomponent processes. Herein we demonstrate a facile method for encapsulating smelly liquid chemicals and its application in a modular palladium-catalyzed carbonylative synthesis of multi-substituted thiophenes from terminal alkynes and aryl iodides as well as a palladium-catalyzed carbonylative synthesis of benzothiophene derivatives from aryl iodides and arylboronic acids. Here, the capsule plays a pivotal role in solving the issues on reaction condition incompatibilities and selectivity of multicomponent reactions as well as avoiding deactivation of the catalyst by releasing the reagents when the reaction temperature is raised. It greatly facilitates the development of highly-efficient multicomponent reactions and demonstrates a modular pathway to obtain functionalized molecules.
      PubDate: 2017-02-06T01:41:00.855801-05:
      DOI: 10.1002/adsc.201601343
  • Lewis Acid-Mediated [3+3] Annulation for the Construction of Substituted
           Pyrimidine and Pyridine Derivatives
    • Authors: Yao Zhou; Zhonghe Tang, Qiuling Song
      Pages: 952 - 958
      Abstract: A direct and single-step procedure towards substituted pyrimidine and pyridine derivatives via Lewis acid-promoted [3+3] annulation between 3-ethoxycyclobutanones and enamines or amidines is presented. Diverse substituted pyrimidine and pyridine derivatives were obtained in good to high yields with a wide substrate scope.
      PubDate: 2017-01-27T03:31:11.076584-05:
      DOI: 10.1002/adsc.201601386
  • Regioselective Enzymatic Carboxylation of Bioactive (Poly)phenols
    • Authors: Katharina Plasch; Verena Resch, Julien Hitce, Jarosław Popłoński, Kurt Faber, Silvia M. Glueck
      Pages: 959 - 965
      Abstract: In order to extend the applicability of the regioselective enzymatic carboxylation of phenols, the substrate scope of o-benzoic acid (de)carboxylases has been investigated towards complex molecules with an emphasis on flavouring agents and polyphenols possessing antioxidant properties. o-Hydroxycarboxylic acid products were obtained with perfect regioselectivity, in moderate to excellent yields. The applicability of this method was proven by the regioselective bio-carboxylation of resveratrol on a preparative scale with 95% yield.
      PubDate: 2017-01-18T05:20:41.487919-05:
      DOI: 10.1002/adsc.201601046
  • Late-Stage Diversification of Non-Steroidal Anti-Inflammatory Drugs by
           Transition Metal-Catalyzed C–H Alkenylations, Thiolations and
    • Authors: Wenbo Ma; Hongbo Dong, Daoxin Wang, Lutz Ackermann
      Pages: 966 - 973
      Abstract: Ruthenium- and silver-catalyzed selective C–H alkenylations, thiolations and selenylations of phenazone (antipyrine) – a non-steroidal anti-inflammatory drug – have been developed. This method features ample substrate scope, affording typically the mono-ortho alkenylated, thiolated and selenylated products in good yields with complete site selectivity control. This strategy offers an efficient protocol for the modification of antipyrine derivatives.
      PubDate: 2017-01-26T09:05:28.630387-05:
      DOI: 10.1002/adsc.201600937
  • Iron-Catalyzed Isopropylation of Electron-Deficient Aryl and Heteroaryl
    • Authors: James N. Sanderson; Andrew P. Dominey, Jonathan M. Percy
      Pages: 1007 - 1017
      Abstract: Traditional methods for the preparation of secondary alkyl-substituted aryl and heteroaryl chlorides challenge both selectivity and functional group tolerance. This contribution describes the use of statistical design of experiments to develop an effective procedure for the preparation of isopropyl-substituted (hetero)arenes with minimal isopropyl to n-propyl isomerization. The reaction tolerates electronically diverse aryl chloride coupling partners, with excellent conversion observed for strongly electron-deficient aromatic rings, such as esters and amides. Electron-rich systems, including methyl- and methoxy-substituted aryl chlorides, were found to be less reactive. Furthermore, the reaction was found to be most successful when heteroaryl chlorides were submitted to the cross-coupling protocol. By mapping substituent effects on reaction selectivity, we were able to show that electron-deficient aryl chlorides are essential for efficient coupling, and use electronic structure calculations to predict the likelihood of successful coupling through the estimation of the electron affinity of each aryl chloride. Moderate isolated yields were achieved with selected aryl chlorides, and moderate to good isolated yields were obtained for all the heteroaryl chlorides coupled. Excellent selectivity was observed when a 2,6-dichloroquinoline was used, allowing mono-substitution on a challenging substrate.
      PubDate: 2017-01-24T03:25:29.378325-05:
      DOI: 10.1002/adsc.201601097
  • Synthesis of Highly Substituted Polyenes by Palladium-Catalyzed
           Cross–Couplings of Sterically Encumbered Alkenyl Bromides and
    • Authors: Miguel Paraja; Raquel Barroso, M. Paz Cabal, Carlos Valdés
      Pages: 1058 - 1062
      Abstract: A new method for the synthesis of polysubstituted conjugated dienes is described, through the palladium-catalyzed cross-coupling between N-tosylhydrazones and alkenyl bromides. The reaction proceeds efficiently when a combination of a highly substituted bromoalkene and a hydrazone derived from a ketone are employed, pointing to the convenience of a sterically encumbered environment. This unprecedented process allows for the stereocontrolled preparation of highly substituted dienes and polyenes.
      PubDate: 2017-01-19T10:06:07.813359-05:
      DOI: 10.1002/adsc.201601155
  • Corrigendum: Recent Advances in Multicomponent Synthesis of
           1,4,5-Trisubstituted 1,2,3-Triazoles
    • Authors: Zhengkai Chen; Zhubo Liu, Gangjian Cao, Hongli Li, Hongjun Ren
      Pages: 1063 - 1063
      PubDate: 2017-03-21T05:22:44.027086-05:
      DOI: 10.1002/adsc.201700150
  • Copper-Catalyzed Remote C−H Amination of Quinolines with
    • Authors: Yao Yin; Jian Xie, Feng-Qing Huang, Lian-Wen Qi, Bo Zhang
      Pages: 1037 - 1042
      Abstract: A copper-catalyzed remote C−H amination of 8-aminoquinoline scaffolds on the C5 position is described. The protocol employs commercially available N-fluorobenzenesulfonimide (NFSI) as the amination reagent and shows broad substrate scope, providing various 5-aminated quinolines in moderate to excellent yields under mild conditions. These reactions feature complete regioselectivity, operational simplicity, and high efficiency.
      PubDate: 2016-12-28T03:00:24.79157-05:0
      DOI: 10.1002/adsc.201600947
  • Nickel-Catalyzed Deoxygenative Deuteration of Aryl Sulfamates
    • Authors: Masami Kuriyama; Shota Kujirada, Kotaro Tsukuda, Osamu Onomura
      Pages: 1043 - 1048
      Abstract: The nickel-catalyzed deoxygenative deuteration of aryl/heteroaryl sulfamates has been developed, and the effective incorporation of deuterium into a variety of aromatic compounds was achieved with sufficient catalytic efficiency and high deuteration degree. This process tolerated reducible functional moieties and heterocyclic structures. Additionally, a double introduction of deuterium also successfully gave a desired product with a high yield and deuterium content.
      PubDate: 2016-12-29T10:55:27.135374-05:
      DOI: 10.1002/adsc.201601105
  • Unveiling the Hidden Performance of Whole Cells in the Asymmetric
    • Authors: Paola Vitale; Vincenzo Mirco Abbinante, Filippo Maria Perna, Antonio Salomone, Cosimo Cardellicchio, Vito Capriati
      Pages: 1049 - 1057
      Abstract: In this contribution, we report the first successful baker's yeast reduction of arylpropanones using deep eutectic solvents (DESs) as biodegradable and non-hazardous co-solvents. The nature of DES [e.g. choline chloride/glycerol (2:1)] and the percentage of water in the mixture proved to be critical for both the reversal of selectivity and to achieve high enantioselectivity on going from pure water (up to 98:2 er in favour of the S-enantiomer) to DES/aqueous mixtures (up to 98:2 er in favour of the R-enantiomer). As a result, both enantiomers of valuable chiral alcohols of pharmaceutical interest were prepared from the same biocatalyst by simply switching the solvent. The possible inhibition of some (S)-oxidoreductases making part of the genome of such a wild-type whole cell biocatalyst when DESs are used as co-solvents may pave the way for an anti-Prelog reduction. The scope and limitations of this kind of biotransformations for a range of aryl-containing ketones are also discussed.
      PubDate: 2016-12-29T10:55:24.220445-05:
      DOI: 10.1002/adsc.201601064
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