Copper-Mediated Trifluoromethylation of Heteroaromatic Compounds by Trifluoromethyl Sulfonium Salts

被引:270
作者
Zhang, Cheng-Pan [1 ]
Wang, Zong-Ling [2 ]
Chen, Qing-Yun [1 ]
Zhang, Chun-Tao [2 ]
Gu, Yu-Cheng [3 ]
Xiao, Ji-Chang [1 ]
机构
[1] Chinese Acad Sci, Shanghai Inst Organ Chem, Key Lab Organofluorine Chem, 345 Lingling Rd, Shanghai 200032, Peoples R China
[2] Hunan Univ Chinese Med, Changsha 410208, Hunan, Peoples R China
[3] Jealotts Hill Int Res Ctr, Bracknell RG42 6EY, Berks, England
关键词
copper; fluorine; heterocycles; sulfonium salts; trifluoromethylation; MILD ELECTROPHILIC TRIFLUOROMETHYLATION; MEDICINAL CHEMISTRY; AROMATIC-COMPOUNDS; ARYL HALIDES; IN-SITU; AGENTS; REAGENTS; FLUORINE; IODINE; (TRIFLUOROMETHYL)COPPER;
D O I
10.1002/anie.201006823
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Copper is king! A convenient method for the synthesis of trifluoromethylated heteroaromatic compounds under mild conditions has been developed based on the observation that 1 can be reduced by certain metals (see scheme). Substrate 1 is assumed to be reduced by copper via a single-electron transfer mechanism, and CuCF3 is the most probable intermediate in this reaction. DMF=N,N-dimethylformamide, Tf=triflate. © 2011 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.
引用
收藏
页码:1896 / 1900
页数:5
相关论文
共 60 条
  • [11] Mild electrophilic trifluoromethylation of secondary and primary aryl- and alkylphosphines using hypervalent iodine(III)-CF3 reagents
    Eisenberger, Patrick
    Kieltsch, Iris
    Armanino, Nicolas
    Togni, Antonio
    [J]. CHEMICAL COMMUNICATIONS, 2008, (13) : 1575 - 1577
  • [12] SYNTHESIS, CHEMISTRY, AND PHOTOCHEMICAL SUBSTITUTIONS OF 6,11-DIHYDRO-5H-PYRROLO[2,1-B][3]BENZAZEPIN-11-ONES
    GIRARD, Y
    ATKINSON, JG
    BELANGER, PC
    FUENTES, JJ
    ROKACH, J
    ROONEY, CS
    REMY, DC
    HUNT, CA
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1983, 48 (19) : 3220 - 3234
  • [13] Desymmetrization of dichloroazaheterocycles
    Goodman, AJ
    Stanforth, SP
    Tarbit, B
    [J]. TETRAHEDRON, 1999, 55 (52) : 15067 - 15070
  • [14] Hiyama T., 2013, ORGANOFLUORINE COMPO
  • [15] Fluorine in medicinal chemistry: A review of anti-cancer agents
    Isanbor, C
    O'Hagan, D
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2006, 127 (03) : 303 - 319
  • [16] Kieltsch I., 2007, ANGEW CHEM, V119, P768
  • [17] Recent advances in electrophilic CF3-transfer using hypervalent iodine(III) reagents
    Kieltsch, Iris
    Eisenberger, Patrick
    Stanek, Kyrill
    Togni, Antonio
    [J]. CHIMIA, 2008, 62 (04) : 260 - 263
  • [18] Mild electrophilic trifluoromethylation of carbon- and sulfur-centered nucleophiles by a hypervalent iodine(III)-CF3 reagent
    Kieltsch, Iris
    Eisenberger, Patrick
    Togni, Antonio
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (05) : 754 - 757
  • [19] Trifluoromethylation of various aromatic compounds by CF3I in the presence of Fe(II) compound, H2O2 and dimethylsulfoxide
    Kino, Tatsuhito
    Nagase, Yu
    Ohtsuka, Yuhki
    Yamamoto, Kyoko
    Uraguchi, Daisuke
    Tokuhisa, Kenji
    Yamakawa, Tetsu
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2010, 131 (01) : 98 - 105
  • [20] Kirsch P., 2013, Modern Fluoroorganic Chemistry