Silver-Catalyzed Hydrotrifluoromethylation of Unactivated Alkenes with CF3SiMe3

被引:249
作者
Wu, Xinyue [1 ]
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
fluorine; homogeneous catalysis; radical reactions; silver; synthetic methods; PD(II)-CATALYZED ORTHO-TRIFLUOROMETHYLATION; COPPER-MEDIATED TRIFLUOROMETHYLATION; ARYL BORONIC ACIDS; OXIDATIVE TRIFLUOROMETHYLATION; ROOM-TEMPERATURE; BOND-FORMATION; ALLYLIC TRIFLUOROMETHYLATION; REDUCTIVE ELIMINATION; ARYLBORONIC ACIDS; TERMINAL ALKENES;
D O I
10.1002/anie.201208971
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A silver bullet: The title reaction results in selective formation of trifluoromethylated alkanes, and is in contrast to the previously reported transition-metal-catalyzed trifluoromethylation of olefins to generate a series of trifluoromethylated allylic compounds. Preliminary mechanistic investigations indicate that the current hydrotrifluoromethylation proceeds through a pathway involving a CF3 radical species. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:2198 / 2202
页数:5
相关论文
共 108 条
  • [1] [Anonymous], 2011, Angew. Chem., DOI [10.1002/ange.201102543, DOI 10.1002/ANGE.201102543]
  • [2] [Anonymous], 2012, ANGEW CHEM INT EDIT
  • [3] [Anonymous], ANGEW CHEM
  • [4] [Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1002/ANGE.201107414
  • [5] [Anonymous], 2012, ANGEW CHEM, DOI DOI 10.1135/CCCC2011078
  • [6] Mechanistic and Computational Studies of Oxidatively-Induced Aryl-CF3 Bond-Formation at Pd: Rational Design of Room Temperature Aryl Trifluoromethylation
    Ball, Nicholas D.
    Gary, J. Brannon
    Ye, Yingda
    Sanford, Melanie S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2011, 133 (19) : 7577 - 7584
  • [7] Aryl-CF3 Bond-Forming Reductive Elimination from Palladium(IV)
    Ball, Nicholas D.
    Kampf, Jeff W.
    Sanford, Melanie S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2010, 132 (09) : 2878 - +
  • [8] Besset T., 2012, ANGEW CHEM, V124, P5134
  • [9] Tamed Arene and Heteroarene Trifluoromethylation
    Besset, Tatiana
    Schneider, Cedric
    Cahard, Dominique
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (21) : 5048 - 5050
  • [10] 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