Visible Light Promoted C-H Functionalization Reactions of Tertiary Amines

被引:22
作者
Liu, Wei [1 ]
Zheng, Xinyu [1 ]
Zeng, Jianguo [1 ,2 ]
Cheng, Pi [1 ,2 ]
机构
[1] Hunan Agr Univ, Natl & Prov Union Engn Res Ctr, Coll Hort & Landscape Architecture, Vet Herbal Med Resources & Initiat, Changsha 410128, Peoples R China
[2] Hunan Agr Univ, Hunan Co Innovat Ctr, Utilizat Botan Funct Ingredients, Changsha 410128, Peoples R China
基金
中国国家自然科学基金;
关键词
tertiary amines; visible light; photoredox catalysis; C-H functionalization; N-ARYL-TETRAHYDROISOQUINOLINES; MERGING PHOTOREDOX CATALYSIS; ELECTRON-DEFICIENT ALKENES; TRANSITION-METAL; ENANTIOSELECTIVE SYNTHESIS; AMINOALKYL RADICALS; GLYCINE DERIVATIVES; CARBONYL-COMPOUNDS; COUPLING REACTION; ACID CATALYSIS;
D O I
10.6023/cjoc201607040
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The tertiary amine motif is an important structure component of multitudinous natural products and drug molecules. Visible light promoted C-H functionalization of tertiary amines has recently received much attention and facilitated the synthesis of alkaloids and drug molecules. Based on photoredox catalysis, visible light is able to induce the formation of iminium cations or alpha-amino carbon radicals through single electron transfer process which can participate in multitudinous type of organic reactions and complete C-H functionalization of tertiary amines. In this review, the research progress of photoredox catalytic C-H functionalization was categorized and summarized.
引用
收藏
页码:1 / 19
页数:19
相关论文
共 73 条
[1]   A Chiral Metal Photocatalyst Architecture for Highly Enantioselective Photoreactions [J].
Amador, Adrian G. ;
Yoon, Tehshik P. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (07) :2304-2306
[2]   Amine Functionalization via Oxidative Photoredox Catalysis: Methodology Development and Complex Molecule Synthesis [J].
Beatty, Joel W. ;
Stephenson, Corey R. J. .
ACCOUNTS OF CHEMICAL RESEARCH, 2015, 48 (05) :1474-1484
[3]   Synthesis of (-)-Pseudotabersonine, (-)-Pseudovincadifformine, and (+)-Coronaridine Enabled by Photoredox Catalysis in Flow [J].
Beatty, Joel W. ;
Stephenson, Corey R. J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (29) :10270-10273
[4]  
Bergonzini G, 2014, CHEM SCI, V5, P112, DOI [10.1039/c3sc52265b, 10.1039/C3SC52265B]
[5]  
Bertrand S, 2000, EUR J ORG CHEM, V2000, P2227
[6]   Visible-Light-Promoted C-C Bond Cleavage: Photocatalytic Generation of Iminium Ions and Amino Radicals [J].
Cai, Shunyou ;
Zhao, Xinyang ;
Wang, Xinbo ;
Liu, Qisong ;
Li, Zigang ;
Wang, David Zhigang .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (32) :8050-8053
[7]   Visible light photoredox-controlled reactions of N-radicals and radical ions [J].
Chen, Jia-Rong ;
Hu, Xiao-Qiang ;
Lu, Liang-Qiu ;
Xiao, Wen-Jing .
CHEMICAL SOCIETY REVIEWS, 2016, 45 (08) :2044-2056
[8]   Visible-Light Photoredox Catalysis: Aza-Henry Reactions via C-H Functionalization [J].
Condie, Allison G. ;
Gonzalez-Gomez, Jose C. ;
Stephenson, Corey R. J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (05) :1464-+
[9]   Visible light photoredox catalysis: regioselective radical addition of aminoalkyl radicals to 2,3-allenoates [J].
Dai, Xiaojun ;
Mao, Renjie ;
Guan, Baochuan ;
Xu, Xiaoliang ;
Li, Xiaonian .
RSC ADVANCES, 2015, 5 (68) :55290-55294
[10]   The Coupling of Tertiary Amines with Acrylate Derivatives via Visible-Light Photoredox Catalysis [J].
Dai, Xiaojun ;
Cheng, Dongping ;
Guan, Baochuan ;
Mao, Wenjuan ;
Xu, Xiaoliang ;
Li, Xiaonian .
JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (15) :7212-7219