Copper-catalyzed synthesis of trifluoromethyl-substituted isoxazolines

被引:136
作者
He, Yu-Tao [1 ]
Li, Lian-Hua [1 ]
Yang, Yan-Fang [1 ]
Wang, Yu-Qi [1 ]
Luo, Jian-Yi [1 ]
Liu, Xue-Yuan [1 ]
Liang, Yong-Min [1 ]
机构
[1] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China
基金
美国国家科学基金会;
关键词
PD(II)-CATALYZED ORTHO-TRIFLUOROMETHYLATION; ARYL BORONIC ACIDS; OXIDATIVE TRIFLUOROMETHYLATION; BOND-FORMATION; NUCLEOPHILIC TRIFLUOROMETHYLATION; MEDIATED TRIFLUOROMETHYLATION; REDUCTIVE ELIMINATION; TRANSITION-METAL; ARENES; ALKENES;
D O I
10.1039/c3cc42588f
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A mild and efficient copper-catalyzed trifluoromethylation reaction which involves the cyclization of oximes has been developed. This method provides a convenient access to a variety of useful CF3-containing 4,5-dihydroisoxazoles by constructing a C-CF3 bond and a C-O bond in one step.
引用
收藏
页码:5687 / 5689
页数:3
相关论文
共 78 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 Vinyl Sulfonates [J].
Cho, Eun Jin ;
Buchwald, Stephen L. .
ORGANIC LETTERS, 2011, 13 (24) :6552-6555
[4]   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
[5]   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
[6]   Copper-Mediated Oxidative Trifluoromethylation of Boronic Acids [J].
Chu, Lingling ;
Qing, Feng-Ling .
ORGANIC LETTERS, 2010, 12 (21) :5060-5063
[7]   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
[8]   Novel 10-I-3 hypervalent iodine-based compounds for electrophilic trifluoromethylation [J].
Eisenberger, P ;
Gischig, S ;
Togni, A .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (09) :2579-2586
[9]   Facile Ar-CF3 bond formation at Pd.: Strikingly different outcomes of reductive elimination from [(Ph3P)2Pd(CF3)Ph] and [(Xantphos)Pd(CF3)Ph] [J].
Grushin, Vladimir V. ;
Marshall, William J. .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) :12644-12645
[10]   Efficient Trifluoromethylation of Activated and Non-Activated Alkenyl Halides by Using (Trifluoromethyl)trimethylsilane [J].
Hafner, Andreas ;
Braese, Stefan .
ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (16) :3044-3048