Recent Advances in Metal-Catalyzed, Electrochemical Coupling Reactions of sp2 Halides/Boronic Acids and sp3 Centers

被引:9
作者
Gale-Day, Zachary J. [1 ]
机构
[1] Univ Calif San Francisco, Chem & Chem Biol, 675 Nelson Rising Ln, San Francisco, CA 94158 USA
来源
SYNTHESIS-STUTTGART | 2021年 / 53卷 / 05期
关键词
electrochemistry; nickel; copper; reduction; cross-coupling; sp(2)-sp(3); ALKYL-HALIDES; ARYL HALIDES; MECHANISTIC ASPECTS; NICKEL CATALYSIS; BROMIDES; REDUCTION; AMINATION; ZINC; DERIVATIVES; STRATEGIES;
D O I
10.1055/s-0040-1706085
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Traditionally, metal-catalyzed cross-coupling reactions rely on stable but expensive metals, such as palladium. However, the recent development of synthetic organic electrochemistry allows for in situ redox manipulations, expanding the use of cheaper, abundant and sustainable metals, such as nickel and copper as efficient cross-coupling catalysts. This short review covers the recent advances in metal-catalyzed electrochemical coupling reactions, with a focus on reactions of sp(2) electrophiles and nucleophiles with sp(3) coupling partners to form both C-C and C-heteroatom bonds. 1 Introduction 2 Nickel-Catalyzed C-C sp(2)-sp(3) Coupling Reactions 3 Coupling of Aryl Groups with Heteroatomic Nuclei 4 Conclusion
引用
收藏
页码:879 / 888
页数:10
相关论文
共 64 条
[31]   Electrochemically Enabled, Nickel-Catalyzed Amination [J].
Li, Chao ;
Kawamata, Yu ;
Nakamura, Hugh ;
Vantourout, Julien C. ;
Liu, Zhiqing ;
Hou, Qinglong ;
Bao, Denghui ;
Starr, Jeremy T. ;
Chen, Jinshan ;
Yan, Ming ;
Baran, Phil S. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (42) :13088-13093
[32]   Ni-Catalyzed Electrochemical Decarboxylative C-C Couplings in Batch and Continuous Flow [J].
Li, Hui ;
Breen, Christopher P. ;
Seo, Hyowon ;
Jamison, Timothy F. ;
Fang, Yuan-Qing ;
Bio, Matthew M. .
ORGANIC LETTERS, 2018, 20 (05) :1338-1341
[33]   Nickel-Catalyzed Thiolation of Aryl Halides and Heteroaryl Halides through Electrochemistry [J].
Liu, Dong ;
Ma, Hong-Xing ;
Fang, Ping ;
Mei, Tian-Sheng .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (15) :5033-5037
[34]   Using Physical Organic Chemistry To Shape the Course of Electrochemical Reactions [J].
Moeller, Kevin D. .
CHEMICAL REVIEWS, 2018, 118 (09) :4817-4833
[35]   Nickel-catalyzed reductive cyclizations and couplings [J].
Montgomery, J .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2004, 43 (30) :3890-3908
[36]   PREPARATION AND SYNTHETIC USE OF THE ZEROVALENT NICKEL-COMPLEX BY ELECTROCHEMICAL REDUCTION [J].
MORI, M ;
HASHIMOTO, Y ;
BAN, Y .
TETRAHEDRON LETTERS, 1980, 21 (07) :631-634
[37]   Synthetic applications and methodology development of Chan-Lam coupling: a review [J].
Munir, Iqra ;
Zahoor, Ameer Fawad ;
Rasool, Nasir ;
Naqvi, Syed Ali Raza ;
Zia, Khalid Mahmood ;
Ahmad, Raheel .
MOLECULAR DIVERSITY, 2019, 23 (01) :215-259
[38]  
Perichon J, 2006, CHEM ORGANOZINC COMP, P755
[39]   Metal-Reductant-Free Electrochemical Nickel-Catalyzed Couplings of Aryl and Alkyl Bromides in Acetonitrile [J].
Perkins, Robert J. ;
Hughes, Alexander J. ;
Weix, Daniel J. ;
Hansen, Eric C. .
ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2019, 23 (08) :1746-1751
[40]   Electrochemical Nickel Catalysis for Sp2-Sp3 Cross-Electrophile Coupling Reactions of Unactivated Alkyl Halides [J].
Perkins, Robert J. ;
Pedro, Dylan J. ;
Hansen, Eric C. .
ORGANIC LETTERS, 2017, 19 (14) :3755-3758