Copper-Mediated Aerobic Oxidative Trifluoromethylation of Terminal Alkynes with Me3SiCF3

被引:260
作者
Chu, Lingling [1 ]
Qing, Feng-Ling [1 ,2 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, Shanghai 200032, Peoples R China
[2] Donghua Univ, Coll Chem Chem Engn & Biotechnol, Shanghai 201620, Peoples R China
基金
中国国家自然科学基金;
关键词
NUCLEOPHILIC TRIFLUOROMETHYLATION; BOND FORMATION; REDUCTIVE ELIMINATION; FACILE SYNTHESES; ORGANIC HALIDES; FLUORINE; FUNCTIONALIZATION; STRATEGIES; ALDEHYDES; IMINES;
D O I
10.1021/ja102175w
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An efficient copper-mediated trifluoromethylation of terminal alkynes with nucleophilic trifluoromethylating reagent (Me3SiCF3) was developed. Both aromatic alkynes and aliphatic alkynes were effective, and a variety of functionalities such as amino, -OMe, -CO2Et, -Br, and -NO2 were tolerated under the reaction conditions. This reaction provides a general, straightforward, and practically useful method to prepare trifluoromethylated acetylenes.
引用
收藏
页码:7262 / +
页数:3
相关论文
共 54 条
[41]   THE 1ST CF3-SUBSTITUTED ORGANYL(CHLORO)SILANES [J].
RUPPERT, I ;
SCHLICH, K ;
VOLBACH, W .
TETRAHEDRON LETTERS, 1984, 25 (21) :2195-2198
[42]   CF3-bearing aromatic and heterocyclic building blocks [J].
Schlosser, Manfred .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (33) :5432-5446
[43]   Modern synthetic methods for fluorine-substituted target molecules [J].
Shimizu, M ;
Hiyama, T .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (02) :214-231
[44]   New preparation and synthetic reactions of 3,3,3-trifluoropropynyllithium, -borate and -stannane: facile synthesis of trifluoromethylated allenes, arylacetylenes and enynes [J].
Shimizu, Masaki ;
Higashi, Masahiro ;
Takeda, Youhei ;
Murai, Masahito ;
Jiang, Guofang ;
Asai, Yuiga ;
Nakao, Yoshiaki ;
Shirakawa, Eiji ;
Hiyama, Tamejiro .
FUTURE MEDICINAL CHEMISTRY, 2009, 1 (05) :921-945
[45]   ELUSIVENESS OF CU-III COMPLEXATION - PREFERENCE FOR TRIFLUOROMETHYL OXIDATION IN THE FORMATION OF [CU-I(CF3)(4)]- SALTS [J].
SNYDER, JP .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1995, 34 (01) :80-81
[46]   POWER-VARIABLE ELECTROPHILIC TRIFLUOROMETHYLATING AGENTS - S-(TRIFLUOROMETHYL)DIBENZOTHIOPHENIUM, SE-(TRIFLUOROMETHYL)DIBENZOSELENOPHENIUM, AND TE-(TRIFLUOROMETHYL)DIBENZOTELLUROPHENIUM SALT SYSTEM [J].
UMEMOTO, T ;
ISHIHARA, S .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1993, 115 (06) :2156-2164
[47]   A NOVEL AND CONVENIENT METHOD FOR TRIFLUOROMETHYLATION OF ORGANIC HALIDES USING CF3SIR3/KF/CU(I) SYSTEM [J].
URATA, H ;
FUCHIKAMI, T .
TETRAHEDRON LETTERS, 1991, 32 (01) :91-94
[48]   Pd(II)-Catalyzed ortho-Trifluoromethylation of Arenes Using TFA as a Promoter [J].
Wang, Xisheng ;
Truesdale, Larry ;
Yu, Jin-Quan .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (11) :3648-+
[49]   Copper-Catalyzed Direct Alkynylation of Electron-Deficient Polyfluoroarenes with Terminal Alkynes Using O2 as an Oxidant [J].
Wei, Ye ;
Zhao, Huaiqing ;
Kan, Jian ;
Su, Weiping ;
Hong, Maochun .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (08) :2522-+
[50]   PREGENERATION, SPECTROSCOPIC DETECTION, AND CHEMICAL-REACTIVITY OF (TRIFLUOROMETHYL)COPPER, AN ELUSIVE AND COMPLEX SPECIES [J].
WIEMERS, DM ;
BURTON, DJ .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1986, 108 (04) :832-834