Recent Advances in Photocatalytic C-N Bond Coupling Reactions

被引:38
作者
Chan, Chun-Ming [1 ]
Chow, Yip-Chi [1 ]
Yu, Wing-Yiu [1 ]
机构
[1] Hong Kong Polytech Univ, State Key Lab Chem Biol & Drug Discovery, Dept Appl Biol & Chem Technol, Hung Hom,Kowloon, Hong Kong, Peoples R China
来源
SYNTHESIS-STUTTGART | 2020年 / 52卷 / 20期
关键词
photochemistry; C-N cross-coupling; amination; radicals; visible light; VISIBLE-LIGHT PHOTOREDOX; H AMINATION; REDUCTIVE AMINATION; CATALYZED SYNTHESIS; ELECTRON-TRANSFER; AMIDATION; ARENES; FUNCTIONALIZATION; RADICALS; COPPER;
D O I
10.1055/s-0040-1707136
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Catalytic C-N bond formation is one of the major research topics in synthetic chemistry owing to the ubiquity of amino groups in natural products, synthetic intermediates and pharmaceutical agents. In parallel with well-established metal-catalyzed C-N bond coupling protocols, photocatalytic reactions have recently emerged as efficient and selective alternatives for the construction of C-N bonds. In this review, the progress made on photocatalytic C-N bond coupling reactions between 2012 and February 2020 is summarized.
引用
收藏
页码:2899 / 2921
页数:23
相关论文
共 148 条
[61]   Formation of Amidinyl Radicals via Visible-Light-Promoted Reduction of N-Phenyl Amidoxime Esters and Application to the Synthesis of 2-Substituted Benzimidazoles [J].
Li, Gang ;
He, Ru ;
Liu, Qiang ;
Wang, Ziwen ;
Liu, Yuxiu ;
Wang, Qingmin .
JOURNAL OF ORGANIC CHEMISTRY, 2019, 84 (13) :8646-8660
[62]   Visible-light-induced condensation cyclization to synthesize benzimidazoles using fluorescein as a photocatalyst [J].
Li, Zhuofei ;
Song, He ;
Guo, Rui ;
Zuo, Minghui ;
Hou, Chuanfu ;
Sun, Shouneng ;
He, Xin ;
Sun, Zhizhong ;
Chu, Wenyi .
GREEN CHEMISTRY, 2019, 21 (13) :3602-3605
[63]   Inverse-electron-demand [4+2] cycloaddition of photogenerated aza-ortho-quinone methides with 1,3,5-triazinanes: access to perfluoroalkylated tetrahydroquinazolines [J].
Liang, Dong ;
Tan, Li-Ping ;
Xiao, Wen-Jing ;
Chen, Jia-Rong .
CHEMICAL COMMUNICATIONS, 2020, 56 (26) :3777-3780
[64]   Visible-Light-Mediated Decarboxylation/Oxidative Amidation of α-Keto Acids with Amines under Mild Reaction Conditions Using O2 [J].
Liu, Jie ;
Liu, Qiang ;
Yi, Hong ;
Qin, Chu ;
Bai, Ruopeng ;
Qi, Xiaotian ;
Lan, Yu ;
Lei, Aiwen .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2014, 53 (02) :502-506
[65]   Transition-Metal-Free C-C, C-O, and C-N Cross-Couplings Enabled by Light [J].
Liu, Wenbo ;
Li, Jianbin ;
Querard, Pierre ;
Li, Chao-Jun .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2019, 141 (16) :6755-6764
[66]   Recent Advances in the Construction of C-N Bonds Through Coupling Reactions between Carbon Radicals and Nitrogen Radicals [J].
Luo, Junfei ;
Wei, Wen-Ting .
ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (11) :2076-2086
[67]   A Visible-Light-Mediated Oxidative C-N Bond Formation/Aromatization Cascade: Photocatalytic Preparation of N-Arylindoles [J].
Maity, Soumitra ;
Zheng, Nan .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (38) :9562-9566
[68]   Decarboxylative C(sp3)-N cross-coupling via synergetic photoredox and copper catalysis [J].
Mao, Runze ;
Frey, Adrian ;
Balon, Jonathan ;
Hu, Xile .
NATURE CATALYSIS, 2018, 1 (02) :120-126
[69]   Direct Aryl C-H Amination with Primary Amines Using Organic Photoredox Catalysis [J].
Margrey, Kaila A. ;
Levens, Alison ;
Nicewicz, David A. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (49) :15644-15648
[70]   Predictive Model for Site-Selective Aryl and Heteroaryl C-H Functionalization via Organic Photoredox Catalysis [J].
Margrey, Kaila A. ;
McManus, Joshua B. ;
Bonazzi, Simone ;
Zecri, Frederic ;
Nicewicz, David A. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (32) :11288-11299