Electrochemical radical-polar crossover: a radical approach to polar chemistry

被引:64
作者
Tan, Zhoumei [1 ]
Zhang, Haonan [1 ]
Xu, Kun [1 ]
Zeng, Chengchu [1 ]
机构
[1] Beijing Univ Technol, Fac Environm & Life, Beijing 100124, Peoples R China
基金
中国国家自然科学基金; 北京市自然科学基金;
关键词
electrosynthesis; radical-polar crossover; radical chemistry; polar chemistry; alkene functionalization; ENOL ACETATES; ALKENES; OXYGENATION; ACTIVATION; AMINATION; ALKYNES;
D O I
10.1007/s11426-023-1735-x
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
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.
引用
收藏
页码:450 / 470
页数:21
相关论文
共 103 条
[1]   Electrochemical Synthesis of gem-Difluoro- and γ-Fluoro-Allyl Boronates and Silanes [J].
Aelterman, Maude ;
Biremond, Tony ;
Jubault, Philippe ;
Poisson, Thomas .
CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (66)
[2]   C-F bond activation under transition-metal-free conditions [J].
Ai, Han-Jun ;
Ma, Xingxing ;
Song, Qiuling ;
Wu, Xiao-Feng .
SCIENCE CHINA-CHEMISTRY, 2021, 64 (10) :1630-1659
[3]   Harnessing Applied Potential: Selective β-Hydrocarboxylation of Substituted Olefins [J].
Alkayal, Anas ;
Tabas, Volodymyr ;
Montanaro, Stephanie ;
Wright, Iain A. ;
Malkov, Andrei V. ;
Buckley, Benjamin R. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (04) :1780-1785
[4]   Electrochemical Benzylic C(sp3)-H Acyloxylation [J].
Atkins, Alexander P. ;
Rowett, Albert C. ;
Heard, David M. ;
Tate, Joseph A. ;
Lennox, Alastair J. J. .
ORGANIC LETTERS, 2022, :5105-5108
[5]   Regio- and Stereoselective Electrochemical Alkylation of Morita-Baylis-Hillman Adducts [J].
Bertuzzi, Giulio ;
Ombrosi, Giada ;
Bandini, Marco .
ORGANIC LETTERS, 2022, 24 (24) :4354-4359
[6]   Electrochemical cascade reactions for electro-organic synthesis [J].
Blank, Skylar ;
Nguyen, Zach ;
Boucher, Dylan G. ;
Minteer, Shelley D. .
CURRENT OPINION IN ELECTROCHEMISTRY, 2022, 35
[7]   Synthesis of gem-Difluoroalkenes through Nickel-Promoted Electrochemical Reductive Cross-Coupling [J].
Chang Zhe ;
Wang Jiaxin ;
Lu Xi ;
Fu Yao .
CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2022, 42 (01) :147-159
[8]   Recent Applications of Homogeneous Catalysis in Electrochemical Organic Synthesis [J].
Cheng, Xu ;
Lei, Aiwen ;
Mei, Tian-Sheng ;
Xu, Hai-Chao ;
Xu, Kun ;
Zeng, Chengchu .
CCS CHEMISTRY, 2022, 4 (04) :1120-1152
[9]   A Broadly Applicable Method for Pd-Catalyzed Carboperfluoro-alkylation of Terminal and Internal Alkynes: A Convenient Route to Tri- and Tetrasubstituted Olefins [J].
Domanski, Sylwester ;
Chaladaj, Wojciech .
ACS CATALYSIS, 2016, 6 (06) :3452-3456
[10]   Regio- and stereoselective electrochemical synthesis of sulfonylated enethers from alkynes and sulfonyl hydrazides [J].
Du, Wu-Bo ;
Wang, Ning-Ning ;
Pan, Chao ;
Ni, Shao-Fei ;
Wen, Li-Rong ;
Li, Ming ;
Zhang, Lin-Bao .
GREEN CHEMISTRY, 2021, 23 (06) :2420-2426