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
[1]   The Role of Intermolecular Hydrogen Bonding and Proton Transfer in Proton-Coupled Electron Transfer [J].
Alligrant, Timothy M. ;
Alvarez, Julio C. .
JOURNAL OF PHYSICAL CHEMISTRY C, 2011, 115 (21) :10797-10805
[2]   Rh(I)-catalyzed coupling cyclization of N-aryl trifluoroacetimidoyl chlorides with alkynes:: One-pot synthesis of fluorinated quinolines [J].
Amii, H ;
Kishikawa, Y ;
Uneyama, K .
ORGANIC LETTERS, 2001, 3 (08) :1109-1112
[3]  
Andrews R.S., 2010, ANGEW CHEM, V122, P7432
[4]   Intermolecular Addition of Glycosyl Halides to Alkenes Mediated by Visible Light [J].
Andrews, R. Stephen ;
Becker, Jennifer J. ;
Gagne, Michel R. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2010, 49 (40) :7274-7276
[5]  
[Anonymous], 2012, ANGEW CHEM-GER EDIT, DOI DOI 10.1021/acs.orglett.5b00684
[6]  
[Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1135/CCCC2011078
[7]  
Baraznenok IL, 1999, EUR J ORG CHEM, V1999, P937
[8]   Pharmacology of N-(3,5-dichloro-1-oxido-4-pyridinyl)-8-methoxy-2-(trifluoromethyl)-5-quinoline carboxamide (SCH 351591), a novel, orally active phosphodiesterase 4 inhibitor [J].
Billah, MM ;
Cooper, N ;
Minnicozzi, M ;
Warneck, J ;
Wang, P ;
Hey, JA ;
Kreutner, W ;
Rizzo, CA ;
Smith, SR ;
Young, S ;
Chapman, RW ;
Dyke, H ;
Shih, NY ;
Piwinski, JJ ;
Cuss, FM ;
Montana, J ;
Ganguly, AK ;
Egan, RW .
JOURNAL OF PHARMACOLOGY AND EXPERIMENTAL THERAPEUTICS, 2002, 302 (01) :127-137
[9]   Proton and electron transfer in the excited state quenching of phenosafranine by aliphatic amines [J].
Broglia, Martin F. ;
Bertolotti, Sonia G. ;
Previtali, Carlos M. .
PHOTOCHEMISTRY AND PHOTOBIOLOGY, 2007, 83 (03) :535-541
[10]   Palladium catalyzed synthesis of 2-trifluoromethylquinolines through a domino Sonogashira-alkyne carbocyclization process [J].
Chen, Zixian ;
Zhu, Jiangtao ;
Xie, Haibo ;
Li, Shan ;
Wu, Yongming ;
Gong, Yuefa .
CHEMICAL COMMUNICATIONS, 2010, 46 (12) :2145-2147