Copper-Catalyzed Decarboxylative Trifluoromethylation of Allylic Bromodifluoroacetates

被引:44
|
作者
Ambler, Brett R. [1 ]
Altman, Ryan A. [1 ]
机构
[1] Univ Kansas, Dept Med Chem, Lawrence, KS 66045 USA
关键词
NUCLEOPHILIC TRIFLUOROMETHYLATION; DIFLUOROCARBENE PRECURSORS; ORGANIC HALIDES; ARYL HALIDES; FLUORINATION; CHLORODIFLUOROACETATE; DERIVATIVES; GENERATION; ANALOGS; ACID;
D O I
10.1021/ol402780k
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The development of new synthetic fluorination reactions has important implications in medicinal, agricultural, and materials chemistries. Given the prevalence and accessibility of alcohols, methods to convert alcohols to trifluoromethanes are desirable. However, this transformation typically requires four-step processes, specialty chemicals, and/or stoichiometric metals to access the trifluoromethyl-containing product. A two-step copper-catalyzed decarboxylative protocol for converting allylic alcohols to trifluoromethanes is reported. Preliminary mechanistic studies distinguish this reaction from previously reported Cu-mediated reactions.
引用
收藏
页码:5578 / 5581
页数:4
相关论文
共 50 条
  • [31] Copper-Catalyzed Trifluoromethylation of N,N-Dialkylhydrazones
    Pair, Etienne
    Monteiro, Nuno
    Bouyssi, Didier
    Baudoin, Olivier
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (20) : 5346 - 5349
  • [32] Copper-Catalyzed Trifluoromethylation of Polysubstituted Alkenes Assisted by Decarboxylation
    He, Zhengbiao
    Tan, Ping
    Hu, Jinbo
    ORGANIC LETTERS, 2016, 18 (01) : 72 - 75
  • [33] Copper-catalyzed trifluoromethylation of alkenes: synthesis of trifluoromethylated benzoxazines
    Jana, Sadhan
    Ashokan, Athira
    Kumar, Shailesh
    Verma, Ajay
    Kumar, Sangit
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2015, 13 (31) : 8411 - 8415
  • [34] Highly Enantioselective Copper-Catalyzed Electrophilic Trifluoromethylation of β-Ketoesters
    Deng, Qing-Hai
    Wadepohl, Hubert
    Gade, Lutz H.
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (26) : 10769 - 10772
  • [35] Copper-catalyzed olefinic trifluoromethylation of enamides at room temperature
    Feng, Chao
    Loh, Teck-Peng
    CHEMICAL SCIENCE, 2012, 3 (12) : 3458 - 3462
  • [36] Copper-catalyzed tandem trifluoromethylation/cyclization of internal alkynes
    Ji, Yun-Long
    Lin, Jin-Hong
    Xiao, Ji-Chang
    Gu, Yu-Cheng
    ORGANIC CHEMISTRY FRONTIERS, 2014, 1 (11): : 1280 - 1284
  • [37] Copper-Catalyzed Trifluoromethylation-Initiated Radical 1,2-Aryl Migration in ,-Diaryl Allylic Alcohols
    Liu, Xiaowu
    Xiong, Fei
    Huang, Xuanping
    Xu, Liang
    Li, Pengfei
    Wu, Xiaoxing
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (27) : 6962 - 6966
  • [38] Copper-Catalyzed Decarboxylative Iodination Reaction in the Gas Phase
    Yin Xinchi
    Jiang You
    Chu Shiying
    Weng Guofeng
    Fang Xiang
    Pan Yuanjiang
    ACTA CHIMICA SINICA, 2018, 76 (06) : 436 - 439
  • [39] Copper-Catalyzed Enantioselective Allylic Substitution with Alkylboranes
    Shido, Yoshinori
    Yoshida, Mika
    Tanabe, Masahito
    Ohmiya, Hirohisa
    Sawamura, Masaya
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (45) : 18573 - 18576
  • [40] Copper-catalyzed allylic amination of olefins with nitrosoarenes
    Srivastava, RS
    TETRAHEDRON LETTERS, 2003, 44 (16) : 3271 - 3274