Cu-Mediated Chemoselective Trifluoromethylation of Benzyl Bromides Using Shelf-Stable Electrophilic Trifluoromethylating Reagents

被引:109
作者
Kawai, Hiroyuki [1 ]
Furukawa, Tatsuya [1 ]
Nomura, Yoshinori [1 ]
Tokunaga, Etsuko [1 ]
Shibata, Norio [1 ]
机构
[1] Nagoya Inst Technol, Grad Sch Engn, Dept Frontier Mat, Showa Ku, Nagoya, Aichi 4668555, Japan
关键词
CATALYZED TRIFLUOROMETHYLATION; ENANTIOSELECTIVE TRIFLUOROMETHYLATION; ORGANIC HALIDES; NUCLEOPHILIC TRIFLUOROMETHYLATION; CONFIGURATIONAL STABILITY; REDUCTIVE ELIMINATION; MEDICINAL CHEMISTRY; CONVENIENT METHOD; BORONIC ACIDS; SALT SYSTEM;
D O I
10.1021/ol201205t
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Copper-mediated chemoselective trifluoromethylation at the benzylic :position by the use of shelf-stable electrophilic trifluoromethylating reagents 3 in good to high yields under mild conditions is described for the first time. The generality of this trifluoromethylation for a wide variety of benzyl bromides facilitates the rapid creation of structural diversity of medicinal candidates in drug discovery.
引用
收藏
页码:3596 / 3599
页数:4
相关论文
共 90 条
  • [11] Novel 10-I-3 hypervalent iodine-based compounds for electrophilic trifluoromethylation
    Eisenberger, P
    Gischig, S
    Togni, A
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (09) : 2579 - 2586
  • [12] CHEMISTRY IN HYDROGEN-FLUORIDE .7. NOVEL SYNTHESIS OF ARYL TRIFLUOROMETHYL ETHERS
    FEIRING, AE
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (16) : 2907 - 2910
  • [13] Filler R., 1993, ORGANOFLUORINE COMPO
  • [14] Filler R., 1982, BIOMEDICINAL ASPECTS
  • [15] Facile Ar-CF3 bond formation at Pd.: Strikingly different outcomes of reductive elimination from [(Ph3P)2Pd(CF3)Ph] and [(Xantphos)Pd(CF3)Ph]
    Grushin, Vladimir V.
    Marshall, William J.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12644 - 12645
  • [16] The many roles for fluorine in medicinal chemistry
    Hagmann, William K.
    [J]. JOURNAL OF MEDICINAL CHEMISTRY, 2008, 51 (15) : 4359 - 4369
  • [17] Structural development of biological response modifiers based on thalidomide
    Hashimoto, Y
    [J]. BIOORGANIC & MEDICINAL CHEMISTRY, 2002, 10 (03) : 461 - 479
  • [18] Cinchona Alkaloid-Catalyzed Asymmetric Trifluoromethylation of Alkynyl Ketones with Trimethylsilyl Trifluoromethane
    Kawai, Hiroyuki
    Tachi, Kentaro
    Tokunaga, Etsuko
    Shiro, Motoo
    Shibata, Norio
    [J]. ORGANIC LETTERS, 2010, 12 (22) : 5104 - 5107
  • [19] Catalytic Enantioselective Trifluoromethylation of Azomethine Imines with Trimethyl(trifluoromethyl)silane
    Kawai, Hiroyuki
    Kusuda, Akihiro
    Nakamura, Shuichi
    Shiro, Motoo
    Shibata, Norio
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (34) : 6324 - 6327
  • [20] Synthesis of novel C2-symmetric chiral crown ethers and their application to enantioselective trifluoromethylation of aldehydes and ketones
    Kawai, Hiroyuki
    Kusuda, Akihiro
    Mizuta, Satoshi
    Nakamura, Shuichi
    Funahashi, Yasuhiro
    Masuda, Hideki
    Shibata, Norio
    [J]. JOURNAL OF FLUORINE CHEMISTRY, 2009, 130 (08) : 762 - 765