Simple and Clean Photoinduced Aromatic Trifluoromethylation Reaction

被引:282
作者
Li, Lu [1 ,2 ]
Mu, Xiaoyue [1 ]
Liu, Wenbo [1 ]
Wang, Yichen [2 ]
Mi, Zetian [2 ]
Li, Chao-Jun [1 ]
机构
[1] McGill Univ, Dept Chem, 801 Sherbrooke St W, Montreal, PQ H3A 0B8, Canada
[2] McGill Univ, Dept Elect & Comp Engn, 3480 Univ St, Montreal, PQ H3A 0E9, Canada
基金
加拿大自然科学与工程研究理事会; 加拿大创新基金会;
关键词
PALLADIUM-CATALYZED TRIFLUOROMETHYLATION; MEDIATED TRIFLUOROMETHYLATION; ADDITIVE-FREE; ARENES; LIGHT; FLUORINE; ARYL; PERFLUOROALKYLATION; PHARMACEUTICALS; HETEROARENES;
D O I
10.1021/jacs.6b02782
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
We describe a simple, metal- and oxidant free photochemical strategy for the direct trifluoromethylation of unactivated arenes and heteroarenes under either ultraviolet or visible light irradiation. We demonstrated that photoexcited aliphatic ketones, such as acetone and diacetyl, can be used as promising low-cost radical initiators to generate CF3 radicals from sodium triflinate efficiently. The broad utility of this strategy and its benefit to medicinal chemistry are demonstrated by the direct trifluoromethylation of unprotected bidentate chelating ligand, xanthine alkaloids, nucleosides, and related antiviral drug molecules.
引用
收藏
页码:5809 / 5812
页数:4
相关论文
共 41 条
[1]   Carbon Trifluoromethylation Reactions of Hydrocarbon Derivatives and Heteroarenes [J].
Alonso, Concepcion ;
Martinez de Marigorta, Eduardo ;
Rubiales, Gloria ;
Palacios, Francisco .
CHEMICAL REVIEWS, 2015, 115 (04) :1847-1935
[2]   A scalable and operationally simple radical trifluoromethylation [J].
Beatty, Joel W. ;
Douglas, James J. ;
Cole, Kevin P. ;
Stephenson, Corey R. J. .
NATURE COMMUNICATIONS, 2015, 6
[3]   Tamed Arene and Heteroarene Trifluoromethylation [J].
Besset, Tatiana ;
Schneider, Cedric ;
Cahard, Dominique .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) :5048-5050
[4]   LIGHT-CATALYZED ORGANIC REACTIONS .1. THE REACTION OF CARBONYL COMPOUNDS WITH 2-METHYL-2-BUTENE IN THE PRESENCE OF ULTRAVIOLET LIGHT [J].
BUCHI, G ;
INMAN, CG ;
LIPINSKY, ES .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1954, 76 (17) :4327-4331
[5]   FLUORINATED ORGANOMETALLICS - PERFLUOROALKYL AND FUNCTIONALIZED PERFLUOROALKYL ORGANOMETALLIC REAGENTS IN ORGANIC-SYNTHESIS [J].
BURTON, DJ ;
YANG, ZY .
TETRAHEDRON, 1992, 48 (02) :189-275
[6]   Chemistry of acyl radicals [J].
Chatgilialoglu, C ;
Crich, D ;
Komatsu, M ;
Ryu, I .
CHEMICAL REVIEWS, 1999, 99 (08) :1991-2069
[7]   Rapid and Efficient Trifluoromethylation of Aromatic and Heteroaromatic Compounds Using Potassium Trifluoroacetate Enabled by a Flow System [J].
Chen, Mao ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (44) :11628-11631
[8]   The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides [J].
Cho, Eun Jin ;
Senecal, Todd D. ;
Kinzel, Tom ;
Zhang, Yong ;
Watson, Donald A. ;
Buchwald, Stephen L. .
SCIENCE, 2010, 328 (5986) :1679-1681
[9]   Copper-Catalyzed Direct C-H Oxidative Trifluoromethylation of Heteroarenes [J].
Chu, Lingling ;
Qing, Feng-Ling .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (02) :1298-1304
[10]   SELECTED ASPECTS OF PHOTOCHEMISTRY .1. PHOTOCHEMISTRY OF CARBONYL-COMPOUNDS [J].
COYLE, JD ;
CARLESS, HAJ .
CHEMICAL SOCIETY REVIEWS, 1972, 1 (04) :465-480