Visible-Light-Induced Radical Cyclization of Trifluoroacetimidoyl Chlorides with Alkynes: Catalytic Synthesis of 2-Trifluoromethyl Quinolines

被引:51
作者
Dong, Xichang [1 ]
Xu, Youwei [1 ]
Liu, Jing Jing [1 ]
Hu, Yumin [1 ]
Xiao, Tiebo [1 ]
Zhou, Lei [1 ]
机构
[1] Sun Yat Sen Univ, Sch Chem & Chem Engn, Guangzhou 510275, Guangdong, Peoples R China
基金
中国国家自然科学基金;
关键词
cyclization; photocatalysis; quinolines; radicals; visible light; C-H FUNCTIONALIZATION; ALPHA-AMINOALKYL RADICALS; PHOTOREDOX CATALYSIS; EFFICIENT SYNTHESIS; ELECTRON-TRANSFER; ORGANIC-REACTIONS; IMIDOYL RADICALS; BOND FORMATIONS; AQUEOUS-MEDIA; TRIPLE BOND;
D O I
10.1002/chem.201303149
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple and efficient method for the synthesis of 2-trifluoromethyl quinolines by means of visible-light-induced radical cyclization of trifluoroacetimidoyl chlorides with alkynes has been developed. This protocol allows the generation of imidoyl radicals by activation of C(sp 2)Cl bonds using a photoredox catalyst under mild and environmentally friendly conditions (see scheme). © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:16928 / 16933
页数:6
相关论文
共 95 条
[51]   Discovery of an α-Amino C-H Arylation Reaction Using the Strategy of Accelerated Serendipity [J].
McNally, Andrew ;
Prier, Christopher K. ;
MacMillan, David W. C. .
SCIENCE, 2011, 334 (6059) :1114-1117
[52]   Imidoyl radicals in organic synthesis [J].
Minozzi, Matteo ;
Nanni, Daniele ;
Spagnolo, Piero .
CURRENT ORGANIC CHEMISTRY, 2007, 11 (15) :1366-1384
[53]   Visible-light-mediated addition of α-aminoalkyl radicals generated from α-silylamines to α,β-unsaturated carbonyl compounds [J].
Miyake, Yoshihiro ;
Ashida, Yuya ;
Nakajima, Kazunari ;
Nishibayashi, Yoshiaki .
CHEMICAL COMMUNICATIONS, 2012, 48 (55) :6966-6968
[54]   Visible-Light-Mediated Utilization of α-Aminoalkyl Radicals: Addition to Electron-Deficient Alkenes Using Photoredox Catalysts [J].
Miyake, Yoshihiro ;
Nakajima, Kazunari ;
Nishibayashi, Yoshiaki .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (07) :3338-3341
[55]   Catalytic Hydrotrifluoromethylation of Unactivated Alkenes [J].
Mizuta, Satoshi ;
Verhoog, Stefan ;
Engle, Keary M. ;
Khotavivattana, Tanatorn ;
O'Duill, Miriam ;
Wheelhouse, Katherine ;
Rassias, Gerasimos ;
Medebielle, Maurice ;
Gouverneur, Veronique .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (07) :2505-2508
[56]   The acidifying effects of chlorine and bromine: Little difference [J].
Mongin, F ;
Schlosser, M .
TETRAHEDRON LETTERS, 1997, 38 (09) :1559-1562
[57]   Trifluoromethylation of arenes and heteroarenes by means of photoredox catalysis [J].
Nagib, David A. ;
MacMillan, David W. C. .
NATURE, 2011, 480 (7376) :224-228
[58]   Enantioselective α-Trifluoromethylation of Aldehydes via Photoredox Organocatalysis [J].
Nagib, David A. ;
Scott, Mark E. ;
MacMillan, David W. C. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (31) :10875-+
[59]   Isonitriles as source and fate of imidoyl radicals: A novel homolytic alpha-fragmentation. [J].
Nanni, D ;
Pareschi, P ;
Tundo, A .
TETRAHEDRON LETTERS, 1996, 37 (52) :9337-9340
[60]   Visible light photoredox catalysis: applications in organic synthesis [J].
Narayanam, Jagan M. R. ;
Stephenson, Corey R. J. .
CHEMICAL SOCIETY REVIEWS, 2011, 40 (01) :102-113