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学者姓名:曾程初
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GB/T 7714 | Tan, Zhoumei , Xu, Kun , Zeng, Chengchu . Copper-catalyzed C-H bond functionalization enabled by programmed alternating current [J]. | SCIENCE CHINA-CHEMISTRY , 2024 . |
MLA | Tan, Zhoumei 等. "Copper-catalyzed C-H bond functionalization enabled by programmed alternating current" . | SCIENCE CHINA-CHEMISTRY (2024) . |
APA | Tan, Zhoumei , Xu, Kun , Zeng, Chengchu . Copper-catalyzed C-H bond functionalization enabled by programmed alternating current . | SCIENCE CHINA-CHEMISTRY , 2024 . |
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Abstract :
The electro-generation of acyl radicals from both aromatic and aliphatic aldehydes remains an unmet challenge. We provide a solution to this challenge by merging electro-oxidation and a quinuclidine-mediated hydrogen atom transfer strategy. The generation of acyl radicals at decreased applied potentials compared to that of formyl oxidation exhibits excellent functional group compatibility. The electro-generation of acyl radicals from both aromatic and aliphatic aldehydes is a synthetic challenge. We addressed this challenge by merging electro-oxidation and a quinuclidine-mediated HAT strategy.
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GB/T 7714 | Li, Yongmei , Sun, Liangbo , Huang, Shengyang et al. Electrochemical quinuclidine-mediated Minisci-type acylation of N-heterocycles with aldehydes [J]. | CHEMICAL COMMUNICATIONS , 2024 , 60 (48) : 6174-6177 . |
MLA | Li, Yongmei et al. "Electrochemical quinuclidine-mediated Minisci-type acylation of N-heterocycles with aldehydes" . | CHEMICAL COMMUNICATIONS 60 . 48 (2024) : 6174-6177 . |
APA | Li, Yongmei , Sun, Liangbo , Huang, Shengyang , Xu, Kun , Zeng, Cheng-Chu . Electrochemical quinuclidine-mediated Minisci-type acylation of N-heterocycles with aldehydes . | CHEMICAL COMMUNICATIONS , 2024 , 60 (48) , 6174-6177 . |
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Abstract :
An electrochemical approach for the Minisci-type acylation of quinoxalines with a-keto acids as the acyl radical precursors is reported. With the assistance of TFA as the key additive, acylated quinoxalines were constructed in synthetically useful yields. The distinguishable features of this electrochemical protocol include catalyst-and external oxidant-free conditions, and operational simplicity.
Keyword :
acyl radical acyl radical anodic oxidation anodic oxidation Minisci reaction Minisci reaction & alpha;-keto acids & alpha;-keto acids electrosynthesis electrosynthesis
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GB/T 7714 | Li, Yongmei , Liang, Sen , Wang, Dehui et al. Electrochemical Decarboxylative Minisci-Type Acylation of Quinoxalines under Catalyst- and External-Oxidant-Free Conditions [J]. | SYNTHESIS-STUTTGART , 2023 , 55 (18) : 3026-3032 . |
MLA | Li, Yongmei et al. "Electrochemical Decarboxylative Minisci-Type Acylation of Quinoxalines under Catalyst- and External-Oxidant-Free Conditions" . | SYNTHESIS-STUTTGART 55 . 18 (2023) : 3026-3032 . |
APA | Li, Yongmei , Liang, Sen , Wang, Dehui , Xu, Kun , Zeng, Chengchu . Electrochemical Decarboxylative Minisci-Type Acylation of Quinoxalines under Catalyst- and External-Oxidant-Free Conditions . | SYNTHESIS-STUTTGART , 2023 , 55 (18) , 3026-3032 . |
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Abstract :
Radical-polar crossover (RPC) reaction bridges the gap between one- and two-electron reactivities, thus providing an ideal solution to overcome the limitations of both radical and polar chemistry. In this manifold, organic electrochemistry provides a uniquely facile strategy to access a diverse array of radical intermediates, thus broadening the chemical space of the RPC concept. This review highlights the synthetic advances in the field of electrochemical RPC reactions since 2020, with an emphasis on the substrate scope, reaction limitation and mechanistic aspect. The related RPC reactions are categorized as net-oxidative, net-reductive, or redox neutral transformations.
Keyword :
alkene functionalization alkene functionalization polar chemistry polar chemistry radical chemistry radical chemistry electrosynthesis electrosynthesis radical-polar crossover radical-polar crossover
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GB/T 7714 | Tan, Zhoumei , Zhang, Haonan , Xu, Kun et al. Electrochemical radical-polar crossover: a radical approach to polar chemistry [J]. | SCIENCE CHINA-CHEMISTRY , 2023 , 67 (2) : 450-470 . |
MLA | Tan, Zhoumei et al. "Electrochemical radical-polar crossover: a radical approach to polar chemistry" . | SCIENCE CHINA-CHEMISTRY 67 . 2 (2023) : 450-470 . |
APA | Tan, Zhoumei , Zhang, Haonan , Xu, Kun , Zeng, Chengchu . Electrochemical radical-polar crossover: a radical approach to polar chemistry . | SCIENCE CHINA-CHEMISTRY , 2023 , 67 (2) , 450-470 . |
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Abstract :
The external oxidant-free exploitation of abundant alkane feedstocks as alkyl radical precursors remains a topic of high interest in synthetic communities. Here, we report a Ce-catalyzed electrophotoredox radical addition/cyclization cascade for the incorporation of unactivated alkanes to produce alkylated benzimidazo-fused isoquinolinones and other N-containing polycycles. Compared with previous works employing prefunctionalized alkyl radical precursors, this electrophotocatalytic protocol features high step-economy. The external oxidant-free conditions accompanied by the generation of H2 as the only byproduct further highlight the high redox- and atom-economy of this catalytic protocol. (c) 2022 Elsevier Inc. All rights reserved.
Keyword :
Unactivated alkane Unactivated alkane Cerium catalysis Cerium catalysis Organic electrosynthesis Organic electrosynthesis LMCT LMCT Electrophotocatalysis Electrophotocatalysis
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GB/T 7714 | Tan, Zhoumei , Jiang, Yangye , Xu, Kun et al. Electrophotoredox/cerium-catalyzed unactivated alkanes activation for the sustainable synthesis of alkylated benzimidazo-fused isoquinolinones [J]. | JOURNAL OF CATALYSIS , 2023 , 417 : 473-480 . |
MLA | Tan, Zhoumei et al. "Electrophotoredox/cerium-catalyzed unactivated alkanes activation for the sustainable synthesis of alkylated benzimidazo-fused isoquinolinones" . | JOURNAL OF CATALYSIS 417 (2023) : 473-480 . |
APA | Tan, Zhoumei , Jiang, Yangye , Xu, Kun , Zeng, Chengchu . Electrophotoredox/cerium-catalyzed unactivated alkanes activation for the sustainable synthesis of alkylated benzimidazo-fused isoquinolinones . | JOURNAL OF CATALYSIS , 2023 , 417 , 473-480 . |
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Abstract :
We report a strategic exploitation of trifluoromethyl thianthrenium triflate (TT-CF3+OTf-) as both electromediator and CF3 radical precursors for paired electrolysis. Enabled by this strategy, the three-component trifluoromethylheteroaromatization of alkenes and alkynes was realized. The superiority of TT-CF3+OTf- to other electrophilic CF3 reagents is attributed to the cathodic generation of thianthrene (TT) as a mediator, which shifts the heterogeneous oxidation of interest to a homogeneous one.
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GB/T 7714 | Xiang, Fang , Wang, Dehui , Xu, Kun et al. Paired Electrolysis Enabled Trifluoromethylheteroaromatization of Alkenes and Alkyne with Trifluoromethyl Thianthrenium Triflate (TT-CF3 +OTf-) as a Bifunctional Reagent [J]. | ORGANIC LETTERS , 2023 , 26 (1) : 411-415 . |
MLA | Xiang, Fang et al. "Paired Electrolysis Enabled Trifluoromethylheteroaromatization of Alkenes and Alkyne with Trifluoromethyl Thianthrenium Triflate (TT-CF3 +OTf-) as a Bifunctional Reagent" . | ORGANIC LETTERS 26 . 1 (2023) : 411-415 . |
APA | Xiang, Fang , Wang, Dehui , Xu, Kun , Zeng, Cheng-Chu . Paired Electrolysis Enabled Trifluoromethylheteroaromatization of Alkenes and Alkyne with Trifluoromethyl Thianthrenium Triflate (TT-CF3 +OTf-) as a Bifunctional Reagent . | ORGANIC LETTERS , 2023 , 26 (1) , 411-415 . |
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Abstract :
The electrochemical utilization of electron-deficient methylarenes for radical-radical cross-couplings remains very rare. Enabled by an umpolung strategy, the unprecedented electrochemical cross-coupling of electron-deficient methylarenes with aldehydes was developed. The paired electrolysis simultaneously generated electron-deficient benzylic radicals and ketyl radicals at both electrodes, which then under-went radical recombination, governed by polarity matching and persistent-radical effect (PRE) to afford functionalized alcohols that are not easily accessible by other methods. This protocol features catalyst-and external redox agent-free conditions and a formal 100% atom economy. Mechanistic studies support the radical-radical cross-coupling pathway.
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GB/T 7714 | Lian, Fei , Xu, Kun , Zeng, Chengchu . Electrochemical Umpolung Enabled Radical-Radical Cross-Coupling Between Electron-Deficient Methylarenes and Aldehydes [J]. | CCS CHEMISTRY , 2023 , 5 (9) : 1973-1981 . |
MLA | Lian, Fei et al. "Electrochemical Umpolung Enabled Radical-Radical Cross-Coupling Between Electron-Deficient Methylarenes and Aldehydes" . | CCS CHEMISTRY 5 . 9 (2023) : 1973-1981 . |
APA | Lian, Fei , Xu, Kun , Zeng, Chengchu . Electrochemical Umpolung Enabled Radical-Radical Cross-Coupling Between Electron-Deficient Methylarenes and Aldehydes . | CCS CHEMISTRY , 2023 , 5 (9) , 1973-1981 . |
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Abstract :
Although the combination of electrochemistry and homogeneous catalysis has proven to be a powerful strategy for achieving a diverse array of novel transformations, some challenges such as controlling the diffusion of catalyst-related species and the instability of catalysts at electrodes remain to be overcome. Herein, we review recent advances in electrochemical homogeneous catalysis, focusing on electrochemical noble-transition-metal catalysis, photoelectrochemical catalysis, and electrochemical enantioselective catalysis. The topics discussed include: (1) how the noblemetal catalystworks in the presence of cathodic hydrogen evolution, (2) how the photocatalyst gets enhanced redox property, and (3) how the enantioselectivity is regulated in a catalytic electrochemical reaction.
Keyword :
transition-metal catalysis transition-metal catalysis electrophotocatalysis electrophotocatalysis enantioselective catalysis enantioselective catalysis homogeneous catalysis homogeneous catalysis electrochemistry electrochemistry
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GB/T 7714 | Cheng, Xu , Lei, Aiwen , Mei, Tian-Sheng et al. Recent Applications of Homogeneous Catalysis in Electrochemical Organic Synthesis [J]. | CCS CHEMISTRY , 2022 , 4 (4) : 1120-1152 . |
MLA | Cheng, Xu et al. "Recent Applications of Homogeneous Catalysis in Electrochemical Organic Synthesis" . | CCS CHEMISTRY 4 . 4 (2022) : 1120-1152 . |
APA | Cheng, Xu , Lei, Aiwen , Mei, Tian-Sheng , Xu, Hai-Chao , Xu, Kun , Zeng, Chengchu . Recent Applications of Homogeneous Catalysis in Electrochemical Organic Synthesis . | CCS CHEMISTRY , 2022 , 4 (4) , 1120-1152 . |
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Abstract :
The organoselenium-catalyzed amination of alkenes is a promising way to construct functionalized amines. However, the use of chemical oxidants and the unavoidable formation of allylic amine or enamine are the two main limitations of these methodologies. Against this background, we herein report an electro-selenocatalytic regime for the hydroazolylation of alkenes with azoles under external oxidant-free conditions with low catalyst loadings. Moreover, this protocol enables the generation of amines without vinyl substituents.
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GB/T 7714 | Tan, Zhoumei , Xiang, Fang , Xu, Kun et al. Electrochemical Organoselenium-Catalyzed Intermolecular Hydroazolylation of Alkenes with Low Catalyst Loadings [J]. | ORGANIC LETTERS , 2022 , 24 (29) : 5345-5350 . |
MLA | Tan, Zhoumei et al. "Electrochemical Organoselenium-Catalyzed Intermolecular Hydroazolylation of Alkenes with Low Catalyst Loadings" . | ORGANIC LETTERS 24 . 29 (2022) : 5345-5350 . |
APA | Tan, Zhoumei , Xiang, Fang , Xu, Kun , Zeng, Chengchu . Electrochemical Organoselenium-Catalyzed Intermolecular Hydroazolylation of Alkenes with Low Catalyst Loadings . | ORGANIC LETTERS , 2022 , 24 (29) , 5345-5350 . |
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Abstract :
Trialkylsilanes are important building blocks in organic synthesis; however, their widespread use in redox chemistry is limited by their high oxidation potentials and comparably high bond dissociation energies (BDEs) of Si-H and alpha-Si-C-H bonds (>92 kcal mol(-1)). Herein, we report a new strategy for Si-H bond homolysis enabled by the synergistic combination of electrooxidation, photoinduced ligand-to-metal charge transfer (LMCT), and radical-mediated hydrogen atom transfer (HAT). Governed by the polarity-matching effect, the HAT to electrophilic MeO. or [Cl-OHCH3] from the more hydridic Si-H instead of a C-H bond allows the selective generation of silyl radicals. This electrophotocatalytic protocol provides rapid access to Si-functionalized benzimidazo-fused isoquinolinones with broad functional-group compatibility. Mechanistic studies have shown that n-Bu4NCl is essential to the electrooxidation of CeCl3 to form the Ce(IV) species. [GRAPHICS] .
Keyword :
electrooxidation electrooxidation electrophotocatalysis electrophotocatalysis LMCT LMCT organic electrosynthesis organic electrosynthesis
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GB/T 7714 | Jiang, Yangye , Xu, Kun , Zeng, Chengchu . Electrophotocatalytic Si-H Activation Governed by Polarity-Matching Effects [J]. | CCS CHEMISTRY , 2022 , 4 (5) : 1796-1805 . |
MLA | Jiang, Yangye et al. "Electrophotocatalytic Si-H Activation Governed by Polarity-Matching Effects" . | CCS CHEMISTRY 4 . 5 (2022) : 1796-1805 . |
APA | Jiang, Yangye , Xu, Kun , Zeng, Chengchu . Electrophotocatalytic Si-H Activation Governed by Polarity-Matching Effects . | CCS CHEMISTRY , 2022 , 4 (5) , 1796-1805 . |
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