Copper-catalyzed olefinic trifluoromethylation of enamides at room temperature

被引:249
作者
Feng, Chao [1 ]
Loh, Teck-Peng [1 ,2 ]
机构
[1] Nanyang Technol Univ, Div Chem & Biol Chem, Sch Phys & Math Sci, Singapore 637616, Singapore
[2] Univ Sci & Technol China, Dept Chem, Hefei 230026, Anhui, Peoples R China
关键词
ENANTIOSELECTIVE ALPHA-TRIFLUOROMETHYLATION; OXIDATIVE TRIFLUOROMETHYLATION; ELECTROPHILIC TRIFLUOROMETHYLATION; TERMINAL ALKENES; BORONIC ACIDS; ARYL; FLUORINE; ARENES; PERFLUOROALKYLATION; IODIDES;
D O I
10.1039/c2sc21164e
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Copper-catalyzed olefinic trifluoromethylation and oxytrifluoromethylation of enamides is reported. The direct olefinic C-H trifluoromethylation constitutes an efficient method for the stereoselective synthesis of beta-trifluoromethyl substituted enamides.
引用
收藏
页码:3458 / 3462
页数:5
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共 71 条
  • [1] The Productive Merger of Iodonium Salts and Organocatalysis: A Non-photolytic Approach to the Enantioselective α-Trifluoromethylation of Aldehydes
    Allen, Anna E.
    MacMillan, David W. C.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (14) : 4986 - +
  • [2] Benzotrifluoride and its halogenated derivatives
    Booth, HS
    Elsey, HM
    Burchfield, PE
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1935, 57 : 2066 - 2069
  • [3] A NEW TRIFLUOROMETHYLATING AGENT - SYNTHESIS OF POLYCHLORINATED (TRIFLUOROMETHYL)BENZENES AND 1,3-BIS(TRIFLUOROMETHYL)BENZENES AND CONVERSION INTO THEIR TRICHLOROMETHYL COUNTERPARTS AND MOLECULAR-STRUCTURE OF HIGHLY STRAINED POLYCHLORO-META-XYLENES
    CASTANER, J
    RIERA, J
    CARILLA, J
    ROBERT, A
    MOLINS, E
    MIRAVITLLES, C
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (01) : 103 - 110
  • [4] COPPER ELECTRON-TRANSFER INDUCED TRIFLUOROMETHYLATION WITH METHYL FLUOROSULPHONYLDIFLUOROACETATE
    CHEN, QY
    YANG, GY
    WU, SW
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 1991, 55 (03) : 291 - 298
  • [5] The Palladium-Catalyzed Trifluoromethylation of Aryl Chlorides
    Cho, Eun Jin
    Senecal, Todd D.
    Kinzel, Tom
    Zhang, Yong
    Watson, Donald A.
    Buchwald, Stephen L.
    [J]. SCIENCE, 2010, 328 (5986) : 1679 - 1681
  • [6] Copper-Catalyzed Oxidative Trifluoromethylation of Terminal Alkenes Using Nucleophilic CF3SiMe3: Efficient C(sp3)-CF3 Bond Formation
    Chu, Lingling
    Qing, Feng-Ling
    [J]. ORGANIC LETTERS, 2012, 14 (08) : 2106 - 2109
  • [7] Copper-Catalyzed Direct C-H Oxidative Trifluoromethylation of Heteroarenes
    Chu, Lingling
    Qing, Feng-Ling
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (02) : 1298 - 1304
  • [8] Copper-Mediated Oxidative Trifluoromethylation of Boronic Acids
    Chu, Lingling
    Qing, Feng-Ling
    [J]. ORGANIC LETTERS, 2010, 12 (21) : 5060 - 5063
  • [9] Copper-Mediated Aerobic Oxidative Trifluoromethylation of Terminal Alkynes with Me3SiCF3
    Chu, Lingling
    Qing, Feng-Ling
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (21) : 7262 - +
  • [10] Metal-Free Oxidative Cyclization of Urea-Tethered Alkenes with Hypervalent Iodine
    Cochran, Brian M.
    Michael, Forrest E.
    [J]. ORGANIC LETTERS, 2008, 10 (21) : 5039 - 5042