Copper-Promoted Sandmeyer Trifluoromethylation Reaction

被引:255
作者
Dai, Jian-Jun [1 ]
Fang, Chi [1 ]
Xiao, Bin [2 ,3 ]
Yi, Jun [1 ]
Xu, Jun [1 ]
Liu, Zhao-Jing [1 ]
Lu, Xi [1 ]
Liu, Lei [2 ,3 ]
Fu, Yao [1 ]
机构
[1] Univ Sci & Technol China, Dept Chem, Hefei 230026, Peoples R China
[2] Tsinghua Univ, Dept Chem, Beijing 100084, Peoples R China
[3] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Oxo Synth & Select Oxidat, Lanzhou 730000, Peoples R China
基金
中国博士后科学基金;
关键词
PALLADIUM-CATALYZED TRIFLUOROMETHYLATION; METAL-FREE BORYLATION; OXIDATIVE TRIFLUOROMETHYLATION; MEDIATED TRIFLUOROMETHYLATION; MEDICINAL CHEMISTRY; BORONIC ACIDS; ARYLBORONIC ACIDS; SULFONIUM SALTS; ARYL RADICALS; ARENES;
D O I
10.1021/ja404217t
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A copper-promoted trifluoromethylation reaction of aromatic amines is described. This transformation proceeds smoothly under mild conditions and exhibits good tolerance of many synthetically relevant functional groups. It provides an alternative approach for the synthesis of trifluoromethylated arenes and heteroarenes. It also constitutes a new example of the Sandmeyer reaction.
引用
收藏
页码:8436 / 8439
页数:4
相关论文
共 73 条
[1]  
Annunziata A, 2001, EUR J ORG CHEM, V2001, P1323
[2]   Aryl-CF3 Bond-Forming Reductive Elimination from Palladium(IV) [J].
Ball, Nicholas D. ;
Kampf, Jeff W. ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) :2878-+
[3]   Catalytic Sandmeyer bromination [J].
Beletskaya, Irina P. ;
Sigeev, Alexander S. ;
Peregudov, Alexander S. ;
Petrovskii, Pavel V. .
SYNTHESIS-STUTTGART, 2007, 16 (16) :2534-2538
[4]   A new rational hypothesis for the pharmacophore of the active metabolite of leflunomide, a potent immunosuppressive drug [J].
Bertolini, G ;
Aquino, M ;
Biffi, M ;
dAtri, G ;
DiPierro, F ;
Ferrario, F ;
Mascagni, P ;
Somenzi, F ;
Zaliani, A ;
Leoni, F .
JOURNAL OF MEDICINAL CHEMISTRY, 1997, 40 (13) :2011-2016
[5]  
Boswell G.A., 1974, ORG REACT, V21, P1
[6]   The Palladium-Catalyzed Trifluoromethylation of Vinyl Sulfonates [J].
Cho, Eun Jin ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2011, 13 (24) :6552-6555
[7]   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
[8]   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
[9]   Copper-Mediated Oxidative Trifluoromethylation of Boronic Acids [J].
Chu, Lingling ;
Qing, Feng-Ling .
ORGANIC LETTERS, 2010, 12 (21) :5060-5063
[10]  
Clarke H.T., 1941, Organic Syntheses, Collective Volume, V1, P514, DOI [10.15227/orgsyn.004.0069, DOI 10.15227/ORGSYN.004.0069]