Recent advances in visible-light photoredox-catalyzed nitrogen radical cyclization

被引:97
作者
Wang, Pengzi [1 ]
Zhao, Quanqing [1 ]
Xiao, Wenjing [1 ,2 ]
Chen, Jiarong [1 ]
机构
[1] Cent China Normal Univ, Coll Chem, CCNU uOttawa Joint Res Ctr, Key Lab Pesticides & Chem Biol,Minist Educ, Wuhan 430079, Peoples R China
[2] Shanghai Inst Organ Chem, State Key Lab Organomet Chem, Shanghai 200032, Peoples R China
来源
GREEN SYNTHESIS AND CATALYSIS | 2020年 / 1卷 / 01期
基金
中国国家自然科学基金;
关键词
Photoredox catalysis; Nitrogen radicals; Radical cyclization reactions; Nitrogen-containing compounds; Nitrogen heterocycles; INTERMOLECULAR 3+2 ANNULATION; IMINYL RADICALS; CENTERED RADICALS; ELECTRON-TRANSFER; RECENT PROGRESS; CASCADE; AMINATION; BOND; HYDROAMINATION; GENERATION;
D O I
10.1016/j.gresc.2020.05.003
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Visible-light photoredox catalysis is a powerful and attractive strategy for organic molecule activation and new reaction design owing to its environmental-friendly characteristics and unique catalytic mechanisms, and has found wide applications in organic synthesis. This catalytic strategy enables controllable generation of diverse nitrogen-centered radicals (NCRs) under mild conditions, providing access to construction of diverse nitrogencontaining compounds. In this review, we critically illustrate the recent advances in the field of visible-light photoredox-catalyzed cyclization of nitrogen-centered radicals, based on the different radical precursors and activation modes. Wherever possible, particular emphasis is also put on working models and synthetic applications.
引用
收藏
页码:42 / 51
页数:10
相关论文
共 86 条
[1]   Visible-Light-Promoted and One-Pot Synthesis of Phenanthridines and Quinolines from Aldehydes and O-Acyl Hydroxylamine [J].
An, Xiao-De ;
Yu, Shouyun .
ORGANIC LETTERS, 2015, 17 (11) :2692-2695
[2]   Cooperative Light-Activated Iodine and Photoredox Catalysis for the Amination of Csp3-H Bonds [J].
Becker, Peter ;
Duhamel, Thomas ;
Stein, Christopher J. ;
Reiher, Markus ;
Muniz, Kilian .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2017, 56 (27) :8004-8008
[3]   Thermolyses of O-phenyl oxime ethers.: A new source of iminyl radicals and a new source of aryloxyl radicals [J].
Blake, JA ;
Pratt, DA ;
Lin, SQ ;
Walton, JC ;
Mulder, P ;
Ingold, KU .
JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (09) :3112-3120
[4]   IMINYL RADICALS .2. RING-OPENING OF CYCLOBUTYL- AND CYCLOPENTYLIMINYL RADICALS [J].
BOIVIN, J ;
FOUQUET, E ;
ZARD, SZ .
TETRAHEDRON, 1994, 50 (06) :1757-1768
[5]   RING-OPENING INDUCED BY IMINYL RADICALS DERIVED FROM CYCLOBUTANONES - NEW ASPECTS OF TIN HYDRIDE CLEAVAGE OF S-PHENYL SULFENYLIMINES [J].
BOIVIN, J ;
FOUQUET, E ;
ZARD, SZ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1991, 113 (03) :1055-1057
[6]   Visible light amination/Smiles cascade: access to phthalazine derivatives [J].
Brachet, Etienne ;
Marzo, Leyre ;
Selkti, Mohamed ;
Koenig, Burkhard ;
Belmont, Philippe .
CHEMICAL SCIENCE, 2016, 7 (08) :5002-5006
[7]   Constructing Heterocycles by Visible Light Photocatalysis [J].
Buden, Maria E. ;
Bardagi, Javier I. ;
Rossi, Roberto A. .
CURRENT ORGANIC SYNTHESIS, 2017, 14 (03) :398-429
[8]   Visible-Light-Promoted Carboimination of Unactivated Alkenes for the Synthesis of Densely Functionalized Pyrroline Derivatives [J].
Cai, Sai-Hu ;
Xie, Jia-Hao ;
Song, Shengjin ;
Ye, Lu ;
Feng, Chao ;
Loh, Teck-Peng .
ACS CATALYSIS, 2016, 6 (08) :5571-5574
[9]   Detection of Fleeting Amine Radical Cations and Elucidation of Chain Processes in Visible-Light-Mediated [3+2] Annulation by Online Mass Spectrometric Techniques [J].
Cai, Yi ;
Wang, Jiang ;
Zhang, Yuexiang ;
Li, Zhi ;
Hu, David ;
Zheng, Nan ;
Chen, Hao .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (35) :12259-12266
[10]   Exploration of Visible-Light Photocatalysis in Heterocycle Synthesis and Functionalization: Reaction Design and Beyond [J].
Chen, Jia-Rong ;
Hu, Xiao-Qiang ;
Lu, Liang-Qiu ;
Xiao, Wen-Jing .
ACCOUNTS OF CHEMICAL RESEARCH, 2016, 49 (09) :1911-1923