Copper-Catalyzed Intermolecular Cyanotrifluoromethylation of Alkenes

被引:128
作者
He, Yu-Tao [1 ]
Li, Lian-Hua [1 ]
Yang, Yan-Fang [1 ]
Zhou, Zhao-Zhao [1 ]
Hua, Hui-Liang [1 ]
Liu, Xue-Yuan [1 ]
Liang, Yong-Min [1 ,2 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
[2] Chinese Acad Sci, Lanzhou Inst Chem Phys, State Key Lab Solid Lubricat, Lanzhou 730000, Peoples R China
关键词
ARYL BORONIC ACIDS; BOND-FORMATION; OXIDATIVE TRIFLUOROMETHYLATION; TERMINAL ALKYNES; REDUCTIVE ELIMINATION; FLUORINE; EFFICIENT; OXYTRIFLUOROMETHYLATION; HYDROXYTRIFLUOROMETHYLATION; HYDROTRIFLUOROMETHYLATION;
D O I
10.1021/ol403263c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A novel and highly practical reaction for the copper-catalyzed intermolecular cyanotrifluoromethylation of alkenes is presented here. This methodology provides a general and straightforward way to synthesize a variety of useful CF3-containing nitriles, which can be used for further preparation of pharmaceutically and agrochemically important compounds in synthetic organic chemistry.
引用
收藏
页码:270 / 273
页数:4
相关论文
共 76 条
[1]   Mechanistic and Computational Studies of Oxidatively-Induced Aryl-CF3 Bond-Formation at Pd: Rational Design of Room Temperature Aryl Trifluoromethylation [J].
Ball, Nicholas D. ;
Gary, J. Brannon ;
Ye, Yingda ;
Sanford, Melanie S. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (19) :7577-7584
[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]   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
[4]   Copper-Catalyzed Oxidative Trifluoromethylation of Terminal Alkenes Using Nucleophilic CF3SiMe3: Efficient C(sp3)-CF3 Bond Formation [J].
Chu, Lingling ;
Qing, Feng-Ling .
ORGANIC LETTERS, 2012, 14 (08) :2106-2109
[5]   Copper-Mediated Oxidative Trifluoromethylation of Boronic Acids [J].
Chu, Lingling ;
Qing, Feng-Ling .
ORGANIC LETTERS, 2010, 12 (21) :5060-5063
[6]   Copper-Mediated Aerobic Oxidative Trifluoromethylation of Terminal Alkynes with Me3SiCF3 [J].
Chu, Lingling ;
Qing, Feng-Ling .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) :7262-+
[7]   Sandmeyer Trifluoromethylation of Arenediazonium Tetrafluoroborates [J].
Danoun, Gregory ;
Bayarmagnai, Bilguun ;
Gruenberg, Matthias F. ;
Goossen, Lukas J. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (31) :7972-7975
[8]   Trifluoromethylation Reactions for the Synthesis of β-Trifluoromethylamines [J].
Egami, Hiromichi ;
Kawamura, Shintaro ;
Miyazaki, Ayako ;
Sodeoka, Mikiko .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (30) :7841-7844
[9]   Alkene Trifluoromethylation Coupled with CC Bond Formation: Construction of Trifluoromethylated Carbocycles and Heterocycles [J].
Egami, Hiromichi ;
Shimizu, Ryo ;
Kawamura, Shintaro ;
Sodeoka, Mikiko .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (14) :4000-4003
[10]   Oxytrifluoromethylation of multiple bonds using copper catalyst under mild conditions [J].
Egami, Hiromichi ;
Shimizu, Ryo ;
Sodeoka, Mikiko .
TETRAHEDRON LETTERS, 2012, 53 (41) :5503-5506