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Science China Chemistry
Journal Prestige (SJR): 0.85  Citation Impact (citeScore): 3 Number of Followers: 2  Hybrid journal (It can contain Open Access articles)ISSN (Print) 1674-7291 - ISSN (Online) 1869-1870 Published by Springer-Verlag  [2468 journals]
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- Preparing lipid nanoparticles with tunable drug loading capacity and
morphology via improved sequential nanoprecipitation-
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PubDate: 2023-11-23
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- Chiral coating-mediated interactions of bacteria with diverse
biointerfaces-
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Abstract: Abstract Bacteria, as living agents, have been widely used for microbial therapy due to their inherent ability to colonize different in vivo microenvironments, particularly in the gut and tumor. The interaction with diverse biointerfaces plays a critical role in bacterial colonization, and thereby determine the ultimate efficacy of microbial therapy. Although surface modification of bacteria with exogenous functional motifs can vary their interaction with surroundings, the effects of surface chirality of modified bacteria on mucous adhesion, tumor cell binding, and bacterial competition remain unknown. Here, we describe surface chirality-dependent selective interactions of bacteria to mucins, tumor cells, and pathogens. By coating bacteria with cationic polyethyleneimine modified with different chiral amino acids through electrostatic interaction, we find that bacteria coated with a D-chiral surface structure exhibit greatly increased adhesion to both mucins and tumor cells compared with those of L- and DL-structures. In addition, by adjusting the chirality of the coating, wrapped probiotic bacteria can selectively resist pathogenic bacteria, showing great potential to enhance colonization and positively modulate the gut and tumor microbiota. This work discloses surface chirality-dependent interaction of bacteria with different biointerfaces, showing a potential to tune the colonization and therapeutic effect of living bacterial agents for disease treatment.
PubDate: 2023-11-22
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- An anthraquinone-based Cu(I) cyclic trinuclear complex for
photo-catalyzing C-C coupling reactions-
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Abstract: Abstract Development of transition metal-based photocatalysts with low cost, strong visible light absorption, and high efficiency is a long-stand pursuit for advanced organic synthesis, yet remains highly challenging. In this article, an anthraquinone-based copper(I) cyclic trinuclear complex (1) was designed and it featured strong visible light absorption, high charge separation efficiency and photochemical properties. Complex 1 as a heterogeneous photocatalyst can efficiently catalyze homo-coupling of terminal alkynes and denitrification-oxidative coupling reaction between hydrazinopyridine and terminal alkynes with excellent yield (up to 99%), broad substrate tolerance (27 examples) and superior reusability (up to 10 cycles without loss of performance) under mild conditions.
PubDate: 2023-11-22
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- Photosensitizing metal-organic layers for photocatalysis, artificial
photosynthesis and fluorescence imaging-
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Abstract: Abstract In recent years, metal-organic layers (MOLs) with high-density and accessible open sites have emerged as a two-dimensional version of metal-organic frameworks (MOFs) with various potential applications. Particularly, MOLs represent a promising platform for photocatalysis, artificial photosynthesis, and fluorescence imaging through the hierarchical assembly of photo-sensitizers and catalysts or other functional groups into MOLs. This review provides an overview of the structural design and synthesis strategies of MOLs with a particular emphasis on the applications of photosensitizing MOLs, illustrating the advantages of the MOLs-based material. The final part discusses perspectives on the challenges encountered in this field and the emerging developments that can be expected.
PubDate: 2023-11-22
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- (Parallel) kinetic resolution of 3,3-disubstituted indolines via
organocatalyzed reactions with azodicarboxylates-
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Abstract: Abstract A novel kinetic resolution (KR) method has been developed for 3,3-disubstituted indolines, whose catalytic asymmetric synthesis remains a significant challenge in organic synthesis. The key to the success of this KR protocol lies in the utilization of chiral phosphoric acid-catalyzed triazane formation reaction with azodicarboxylates, which enables the enantioselective synthesis of various substituted indolines bearing C3-quaternary stereocenters with good to high enantioselectivities (with s-factors up to 70). Moreover, an intriguing parallel kinetic resolution (PKR) has been developed by combining triazane formation and dehydrogenation reactions using different azodicarboxylates. Experimental studies have provided insight into the mechanism of this PKR reaction, demonstrating stereoselectivity in both triazane formation and dehydrogenation steps, favoring the opposite enantiomers. The large-scale synthesis and diverse derivatizations of the products, particularly the imine group-containing 3H-indoles, demonstrate the value of these (P)KR methods.
PubDate: 2023-11-21
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- Lighting up nonbenzenoid acepleiadylene with ultra-narrowband emission
through aromaticity modulation-
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Abstract: Abstract Nonbenzenoid polycyclic arenes have attracted great attention because of their unique topological structures and appealing properties; however, they are generally considered as poor luminescent materials due to the ring puckering behavior of the nonhexagons. Acepleiadylene (APD), a nonbenzenoid isomer of pyrene, has been demonstrated as an excellent building block for optoelectronic applications, but its poor photoluminescence quantum yield (PLQY) has hampered its application in luminescent materials. Considering that the ring puckering character can be suppressed by increasing the rigidity of the nonhexagon rings, herein, we propose a novel strategy for enhancing the aromaticity of the nonhexagons to improve the PLQYs of APD derivatives. Electron-withdrawing cyano groups are introduced on the five-membered ring of APD to enhance the charge-separated character and thus the aromaticity of the nonhexagons, endowing the cyano-substituted APDs (CNAPD and 2CNAPD) with better rigidity. Therefore, the cyano substitution successfully suppresses the nonradiative energy dissipation caused by the ring puckering, improving the PLQY from 2.4% for APD to 14% for CNAPD, and to 63% for 2CNAPD. In addition, the enhanced rigidity also suppresses the vibration sideband of the photoluminescence spectra, leading to an ultra-narrowband emission from 2CNAPD with a full-width at half-maximum (FWHM) of 13 nm (47 meV), which is a new record in organic molecules. These results demonstrate that APD derivatives have great potential in highly efficient luminescent materials with high color purity via the aromaticity regulation strategy, which provides a novel concept for designing nonbenzenoid luminescent materials.
PubDate: 2023-11-21
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- Organoboron chemistry towards controlled and precise polymer synthesis
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Abstract: Abstract Organoboron reagents have garnered considerable attention due to their distinct properties. In recent years, boronic acids and boronate esters have been important intermediates for cross-coupling reactions and other functional group construction and are often used to synthesize small organic molecules, drugs, and bioactive substances. In this feature article, we encapsulate the strategy of harnessing the unique properties of organoboron reagents to overcome challenges encountered in conventional polymer synthesis. We delve into the synthesis of boron-containing monomers and polymer materials, unraveling the unique attributes of these newfound polymers while offering innovative insights into their application within recyclable or reprocessable materials. We develop organoboron-based photocatalysts, employing their inner-sphere electron transfer (ISET) mechanisms to initiate controlled radical polymerization. We utilize alkylborane to initiate controlled radical polymerization and further designed B-alkylcatecholboranes to prepare ultra-high molecular weight polymers. Notably, we also propose a liquid-phase synthesis method based on organoboron tags and apply it to the precise synthesis of sequence-controlled conjugated polymers. These advancements open up new frontiers in the realm of polymer science, and the versatility and potential of organoboron reagents in polymer synthesis continue to inspire exciting research endeavors.
PubDate: 2023-11-21
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- Polymer-based synthetic oncolytic virus-like nanoparticles for cancer
immunotherapy-
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Abstract: Abstract Oncolytic viruses have emerged as new powerful therapeutic agents for cancer therapy by specifically lysing cancer cells while activating innate immune responses at the same time. However, due to the thorny issues of safety concerns and host immune reaction, the clinical application of oncolytic viruses is still limited. Herein, we report a rationally designed oncolytic virus-like nanoparticles (OV-NPs) composed of stimulator of interferon genes (STING)-stimulating polymer loaded with therapeutic genes for cancer immunotherapy. After injection into tumor, the OV-NPs carrying OX40L plasmid could reprogram tumor cells to express OX40L immune checkpoint molecules and activate the STING pathway for cooperatively enhancing antitumor immunity, with a tumor suppression rate of 92.3% in B16F10 tumor model and 78.7% in MC38 tumor model without causing any toxicity. The OV-NPs could be further applied in carrying other plasmids (IL-12) and utilization in gene combination therapy. This study should inspire designing synthetic OV-NPs as alternative strategies for extending oncolytic virus application in cancer immunotherapy.
PubDate: 2023-11-21
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- Material and device design for organic solar cells: towards efficiency and
stability-
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Abstract: Abstract Organic solar cells (OSCs) have garnered significant attention as a novel photovoltaic technology and have been extensively investigated. In recent years, OSCs have made rapid strides in power conversion efficiency (PCE), demonstrating their significant potential in practical applications. In addition to high PCE, the practical application of OSCs demands a prolonged operating lifespan. The rational design of materials and devices to achieve efficient and stable OSCs is pivotal. This feature article presents a thorough analysis of our group’s studies on enhancing efficiency and stability through material and device design. We introduce a range of exceptional chlorine-mediated organic photovoltaic materials and systematically summarize chlorine atom (Cl) induced effects on energy levels, molecular stacking, active layer film morphology and photovoltaic performance. Furthermore, the use of single-crystal diffraction technology allows for a comprehensive understanding of inter-molecular packing and interaction at the molecular level. A series of highly efficient non-fullerene acceptors (NFAs) with three-dimensional (3D) network packing structures are developed and discussed. Subsequently, based on efficient 3D network brominated NFAs, the studies on polymer and oligomer acceptor materials are carried out and achieve efficient and stable OSCs. In addition to materials design, the development of the “quasiplanar heterojunction” (Q-PHJ) based OSC device also plays an important role in achieving superior efficiency and stability. These design experiences of materials and devices hope to provide valuable guidance for the development of efficient and stable OSCs.
PubDate: 2023-11-21
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- Recent advances in fluorinated polymers: synthesis and diverse
applications-
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Abstract: Abstract Fluorinated polymers exhibit a unique combination of attributes, including chemical inertness, low surface energy, exceptional weather resistance, and intriguing electrical properties. This mini review provides an overview of recent advancements in the research of fluorinated polymers, highlighting the development of synthetic strategies for novel fluorinated polymers and their diverse applications in various fields. Traditional fluorinated polyolefins can be modified through chemical methods to produce functional materials. Copolymerization of fluorinated olefins with non-fluorinated monomers effectively addresses synthesis challenges, yielding main-chain fluoro-containing polymers with specific functional groups. Additionally, recent studies have revealed that free radical (co)polymerization of fluorinated (meth)acrylate monomers leads to new fluorinated polymers with enhanced solubility, processability, and structural diversity. Capitalizing on these new synthetic strategies, a range of fluorinated polymer materials has been developed for a multitude of applications, including flexible electrodes, alternating current (AC) electroluminescent devices, energy storage capacitors, triboelectric nanogenerators, and lithium batteries. With their customized structures and excellent properties, fluorinated polymers hold significant promise to uncover more potential applications in the era of flexible and wearable electronics.
PubDate: 2023-11-20
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- Efficient photothermal CO2 methanation over NiFe alloy nanoparticles with
enhanced localized surface plasmon resonance effect-
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Abstract: Abstract The methanation of CO2 using green hydrogen not only consumes CO2 as a carbon resource but also stores H2 with high density. However, the activation of CO2 molecules under mild conditions is challenging due to their inert nature. Herein, we report an efficient photothermal catalytic system using light irradiation which realizes the complete conversion of CO2 to methane without external heating. Over optimum bimetallic NiFe nanoparticles (NPs) with a Ni/Fe atomic ratio of 7, the CO2 conversion can reach up to 98% with a CH4 selectivity of 99%, and no catalyst deactivation was observed for more than 100 h, outperforming the reported catalysts. The catalytic performance is strongly dependent on the structure promoters, light absorption efficiency, NiFe particle sizes, and Ni/Fe ratio. The NiFe alloy NPs with an average size of ~21 nm dispersed on alumina nanosheets are evidenced to enhance the localized surface plasmon resonance (LSPR) effect, thus efficiently triggering the CO2 methanation. This work emphasizes and clarifies the important role of LSPR in CO2 hydrogenation, which may benefit the rational utilization of CO2 using solar power.
PubDate: 2023-11-20
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- Interplay between geometric and electronic structures of Pt entities over
TiO2 for CO oxidation-
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Abstract: Abstract Monodispersed Pt colloids with a mean size of 2 nm were deposited uniformly on the {110} facets of a rod-shaped rutile TiO2, forming a well-defined Pt/TiO2 system. Oxidative treatment of this precursor at elevated temperatures re-dispersed the Pt particles into clusters and single-atoms. Air-calcination at 673 K partially oxidized the Pt particle surface, while calcination at 773 K yielded PtOx clusters of 1.6 nm in 7–8 atomic layers. Further calcination at 873 K formed a mixture of raft-like PtOx clusters (1.6 nm, 1–2 atomic layers) and cationic single-atoms. When tested for CO oxidation at 373 K, the Pt particles showed a higher activity than the PtOx clusters, whereas the cationic single-atoms were much less active. Subsequent H2-reduction at 473 K converted the partially oxidized Pt particles into the metallic species, but they were encapsulated by TiO2−x overlayers because of the strong metal–support interactions, which decreased the activity dramatically. H2-reduction of the PtOx clusters at 473 K enhanced the fraction of metallic Pt species without changing the size and geometry, and promoted the activity substantially. H2-treatment of Pt single-atoms at 473 K increased the activity only moderately because most Pt species still kept at cationic species. These results straightforwardly differentiated the catalytic behavior of Pt particles, clusters and single-atoms at the same metal loading and over the same TiO2 support, and further demonstrated that the electronic structures of Pt entities played a decisive role in the catalytic oxidation, in addition to the specified sizes.
PubDate: 2023-11-20
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- Highly efficient ternary organic solar cells with excellent open-circuit
voltage and fill factor via precisely tuning molecular stacking and
morphology-
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Abstract: Abstract The micro-morphology and molecular stacking play a key role in determining the charge transport process and nonradiative energy loss, thus impacting the performances of organic solar cells (OSCs). To address this issue, a non-fullerene acceptor PhC6-IC-F with alkylbenzene side-chain, possessing optimized molecular stacking, complementary absorption spectra and forming a cascade energy level alignment in the PM6:BTP-eC9 blend, is introduced as guest acceptor to improve efficiency of ternary OSCs. The bulky phenyl in the side-chain can regulate crystallinity and optimizing phase separation between receptors in ternary blend films, resulting in the optimal phase separations in the ternary films. As a result, high efficiencies of 18.33% as photovoltaic layer are obtained for PhC6-IC-F-based ternary devices with excellent fill factor (FF) of 78.92%. Impressively, the ternary system produces a significantly improved open circuit voltage (Voc) of 0.857 V compared with the binary device, contributing to the reduced density of trap states and suppressed non-radiative recombination result in lower energy loss. This work demonstrates an effective approach for adjusting the aggregation, molecular packing and fine phase separation morphology to increase Voc and FF, paving the way toward high-efficiency OSCs.
PubDate: 2023-11-17
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- Regioselective and asymmetric allylic alkylation of vinyl epoxides for the
construction of allylic alcohols via synergistic catalysis-
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Abstract: Abstract A highly efficient asymmetric allylic alkylation of cyclic and acyclic carbon nucleophiles with vinyl epoxides has been developed, which exhibits good functional group compatibility, high atomic and step economy. This protocol utilizes a strategy of synergistic catalysis with a chiral N,N′-dioxide/NiII complex and an achiral Pd0 catalyst, generating a series of multi-substituted allylic alcohols with a quaternary carbon stereocenter in high yield and excellent regio-, Z/E- and enantioselectivity under mild conditions. Further transformations of the product demonstrate the potential utility of this protocol in the synthesis of allyl alcohol derivatives and natural product analogues. Experimental studies revealed that the N,N′-dioxide/metal complexes play an important role in controlling the Z/E- and enantioselectivity. The density functional theory (DFT) calculations further demonstrated that multiple C–H;·;·;·π interactions between the aromatic rings of the two substrates and the amide moiety in the ligand stabilized the dominant transition state.
PubDate: 2023-11-17
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- Photocatalyzed ditrifluoromethylthiolation of alkenes with CF3SO2Na
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Abstract: Abstract Since the first report of sodium trifluoromethanesulfinate (CF3SO2Na) as an electrophilic trifluoromethylthiolation reagent in 2015, there has been no breakthrough in research in this field. Herein, we disclose an unprecedented usage of CF3SO2Na as a radical trifluoromethylthiolation reagent. A photocatalyzed ditrifluoromethylthiolation of alkenes with CF3SO2Na in the presence of PPh3 and catalytic copper has been developed. Interestingly, either Ir[(p-Fppy)2(bpy)]PF6 or Ir(ppy)3 could facilitate this transformation. Mechanistic studies indicate that initiation of the radical chain proceeded via two different photocatalytic quenching mechanisms. This protocol provides a practical method for the construction of diverse vicinal ditrifluoromethylthiolated compounds.
PubDate: 2023-11-17
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- Design of stable covalent organic frameworks for transport regulation of
mass and energy-
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Abstract: Abstract This feature article discusses the design of stable covalent organic frameworks (COFs) for the transport regulation of protons, electrons, and radicals. Transporting these particles through materials is essential for many applications, and porous materials with high surface area and porosity have become powerful platforms for their development. However, the stability of the holes in the material is crucial for adjusting the transmission performance, which may change significantly when the material is not stable enough, and the structure changes when it is in service in the environment. Various strategies have been adopted to improve the stability of COFs, including introducing strong electron-donating groups into the COFs and introducing irreversible reactions into the COF synthesis process. The transport regulation in stable COFs has been explored, and the structure-function relationship has been established. The prospects and challenges of COFs for the transport regulation of protons, electrons, and radicals have also been discussed. Overall, the breakthroughs in COF field have opened new possibilities for developing advanced materials with improved transport properties. The stable COFs have potential applications in energy storage, catalysis, and sensing. However, further research is needed to understand the transport properties of COFs fully and to optimize their performance for specific applications.
PubDate: 2023-11-17
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- Catalytic asymmetric synthesis of sulfur-containing atropisomers by C-S
bond formations-
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Abstract: Abstract Chiral organosulfur compounds are not only widely distributed in bioactive natural products and pharmaceuticals, but also play a significant role in chiral ligands/catalysts. Throughout the history of synthetic organic chemistry, chemists have been absorbed in the construction of centrally chiral organosulfur compounds. Nevertheless, there are relatively few reports on installing sulfur functional groups into axially chiral compounds. Atropisomerism is one of the fundamental phenomena in nature, which ubiquitously exists in natural products. After more than a century of development, atropisomers have been designed and extensively applied to pharmaceuticals, functional materials and chiral ligands/catalysts. Due to the importance of chiral sulfur-containing atropisomers, there is an increasing demand for enantioselective synthesis of them. Recently, a diversity of approaches by C-S bond formations have been established for the construction of enantioenriched sulfur-containing atropisomers, however, there is no comprehensive review to summarize this great progress. In this mini-review, we summarize recent progress in catalytic asymmetric synthesis of sulfur-containing atropisomers by C-S bond formations, which includes sulfur nucleophilic reactions, sulfur electrophilic reactions and sulfur radical reactions. Furthermore, the reaction mechanisms are also discussed. We hope that this mini-review will enable more researchers to further explore this field.
PubDate: 2023-11-17
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- Confluence of asymmetric catalysis and electrosynthesis in sustainable
chemical transformations-
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PubDate: 2023-11-16
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- Reduction of unactivated alkyl chlorides enabled by light-induced single
electron transfer-
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Abstract: Abstract Alkyl chlorides are abundant and easily accessible starting materials. However, due to the high reduction potentials associated with unactivated alkyl chlorides, achieving their single electron reduction remains a persistent challenge. This challenge has spurred the exploration of efficient activation methods to overcome this issue. In recent years, photocatalysis has emerged as a mild and potent tool for the single electron reduction of unactivated alkyl chlorides, opening up new possibilities in this field. Considering the rapid advancements in this area, a comprehensive review that provides a conceptual understanding of this emerging field, with a specific focus on reaction design and catalytic mechanisms, would be timely and highly valuable. Hence, we present an overview of various synthetic techniques for photoinduced single electron reduction of unactivated alkyl chlorides. Furthermore, we also discuss the limitations of the present methods and future directions that lie ahead in this field.
PubDate: 2023-11-16
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- Selective control of secondary alcohols upgrading using Ir-catalyzed
cross-coupling strategy-
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Abstract: Abstract The selective coupling of alcohols is a fascinating yet challenging approach for upgrading alcohols. Herein, we accomplished the controlled production of β-disubstituted ketones or upgraded secondary alcohols via the Ir-catalyzed cross-coupling of secondary alcohols in excellent yields with broad substrate scopes. This selective control was achieved by using an in-situ generated mono-NHC-Ir or a tris-NHC-Ir complex as the catalysts, respectively. Mechanistic studies reavealed that the delicate balance between dehydrogenation and hydrogenation abilities of these bifunctional catalysts is crucial for achieving different selectivity. The tris-NHC-Ir complex effectively facilitated dehydrogenation of alcohols and hydrogenation of intermediates, leading to the desired upgraded secondary alcohols. Conversely, the high dehydrogenation ability of the mono-NHC-Ir complex promoted the conversion of formed secondary alcohols back to ketones.
PubDate: 2023-11-16
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