Copper-catalyzed gem-difluoromethylenation of C(sp2)-H bonds of alkenes

被引:19
作者
Xu, Hui [1 ]
Wang, Dejing [1 ]
Chen, Yunrong [1 ]
Wan, Wen [1 ]
Deng, Hongmei [2 ]
Ma, Kesen [3 ]
Wu, Shaoxiong [4 ]
Hao, Jian [1 ,5 ]
Jiang, Haizhen [1 ,5 ]
机构
[1] Shanghai Univ, Innovat Drug Res Ctr, Dept Chem, Shanghai 200444, Peoples R China
[2] Shanghai Univ, Lab Microstruct, Shanghai 200444, Peoples R China
[3] Univ Waterloo, Dept Biol, 200 Univ Ave West, Waterloo, ON N2L 3G1, Canada
[4] Emory Univ, Emory NMR Res Ctr, 201 Dowman Dr, Atlanta, GA 30322 USA
[5] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
基金
中国国家自然科学基金;
关键词
C-H FUNCTIONALIZATION; TERMINAL ALKENES; RECENT PROGRESS; TRIFLUOROMETHYLATION; DIFLUOROACETYLATION; FLUOROALKYLATION; INHIBITORS; CHEMISTRY; ARYLATION; FLUORINE;
D O I
10.1039/c7qo00119c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper-catalyzed gem-difluoromethylenation of the C(sp(2))-H bonds of alkenes with high functional group tolerance has been developed. This protocol is the first to efficiently achieve gem-difluoromethylenation of C(sp(2))-H bonds of unactivated aliphatic terminal olefins and can be applied in a reaction cascade to achieve gem-difluoromethylenation/cyclization of alkenes.
引用
收藏
页码:1239 / 1243
页数:5
相关论文
共 62 条
[1]   Nanomolar Potency and Metabolically Stable Inhibitors of Kidney Urea Transporter UT-B [J].
Anderson, Marc O. ;
Zhang, Jicheng ;
Liu, Yan ;
Yao, Chenjuan ;
Phuan, Puay-Wah ;
Verkrnan, A. S. .
JOURNAL OF MEDICINAL CHEMISTRY, 2012, 55 (12) :5942-5950
[2]  
ANDO K, 1995, CHEM PHARM BULL, V43, P189
[3]   Copper in cross-coupling reactions - The post-Ullmann chemistry [J].
Beletskaya, IP ;
Cheprakov, AV .
COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) :2337-2364
[4]   Recent Progress toward the Introduction of Functionalized Difluoromethylated Building Blocks onto C(sp2) and C(sp) Centers [J].
Belhomme, Marie-Charlotte ;
Besset, Tatiana ;
Poisson, Thomas ;
Pannecoucke, Xavier .
CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (37) :12836-12865
[5]   Copper Catalyzed β-Difluoroacetylation of Dihydropyrans and Glycals by Means of Direct C-H Functionalization [J].
Belhomme, Marie-Charlotte ;
Poisson, Thomas ;
Pannecoucke, Xavier .
ORGANIC LETTERS, 2013, 15 (13) :3428-3431
[6]   Recent Progress in Direct Introduction of Fluorinated Groups on Alkenes and Alkynes by means of C-H Bond Functionalization [J].
Besset, Tatiana ;
Poisson, Thomas ;
Pannecoucke, Xavier .
CHEMISTRY-A EUROPEAN JOURNAL, 2014, 20 (51) :16830-16845
[7]   Tamed Arene and Heteroarene Trifluoromethylation [J].
Besset, Tatiana ;
Schneider, Cedric ;
Cahard, Dominique .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) :5048-5050
[8]  
Bgu J.-P., 2008, Bioorganic and Medicinal Chemistry of Fluorine
[9]   Solvent effect on intramolecular hydrogen bonds in push-pull conjugated molecules [J].
Bouchy, A ;
Rinaldi, D ;
Rivail, JL .
INTERNATIONAL JOURNAL OF QUANTUM CHEMISTRY, 2004, 96 (03) :273-281
[10]   C-H functionalization/C-N bond formation: Copper-catalyzed synthesis of benzimidazoles from amidines [J].
Brasche, Gordon ;
Buchwald, Stephen L. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2008, 47 (10) :1932-1934