Synthesis of trifluoromethylated acetylenes via copper-catalyzed trifluoromethylation of alkynyltrifluoroborates

被引:33
|
作者
Zheng, Huidong [3 ]
Huang, Yuanyuan [3 ]
Wang, Zhiwei [3 ]
Li, Huaifeng [1 ,2 ]
Huang, Kuo-Wei [1 ,2 ]
Yuan, Yaofeng [3 ]
Weng, Zhiqiang [3 ]
机构
[1] King Abdullah Univ Sci & Technol, KAUST Catalysis Ctr, Thuwal 239556900, Saudi Arabia
[2] King Abdullah Univ Sci & Technol, Div Chem & Life Sci & Engn, Thuwal 239556900, Saudi Arabia
[3] Fuzhou Univ, Coll Chem & Chem Engn, Fuzhou 350108, Fujian, Peoples R China
基金
中国国家自然科学基金;
关键词
Copper catalysis; Trifluoromethylated acetylenes; Trifluoromethylation; Alkynyltrifluoroborates; ARYL BORONIC ACIDS; TERMINAL ALKYNES; INTERNAL ALKYNES; CHEMISTRY; REAGENT;
D O I
10.1016/j.tetlet.2012.09.083
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new method for the synthesis of trifluoromethylated acetylenes is developed which involves the copper-catalyzed trifluoromethylation of alkynyltrifluoroborates with an electrophilic trifluoromethylating reagent. This method offers significant advantages such as efficiency and mild and base-free reaction conditions. A plausible mechanism is proposed. (c) 2012 Published by Elsevier Ltd.
引用
收藏
页码:6646 / 6649
页数:4
相关论文
共 50 条
  • [31] Copper-Catalyzed Synthesis of Difluoromethyl Alkynes from Terminal and Silyl Acetylenes
    Ispizua-Rodriguez, Xanath
    Krishnamurti, Vinayak
    Carpio, Vanessa
    Barrett, Colby
    Prakash, G. K. Surya
    JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (02): : 1194 - 1199
  • [32] Copper-Catalyzed Aromatic Trifluoromethylation via Group Transfer from Fluoral Derivatives
    Kondo, Hideaki
    Oishi, Masahiro
    Fujikawa, Kenichi
    Amii, Hideki
    ADVANCED SYNTHESIS & CATALYSIS, 2011, 353 (08) : 1247 - 1252
  • [33] Copper-catalyzed cycloaddition of azides and acetylenes.
    Rostovtsev, VV
    Green, L
    Sharpless, KB
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 224 : U186 - U186
  • [34] Copper-catalyzed tandem trifluoromethylation-cyclization of olefinic carbonyls: synthesis of trifluoromethylated 2,3-dihydrofurans and 3,4-dihydropyrans
    Bai, Xiaohui
    Lv, Leiyang
    Li, Zhiping
    ORGANIC CHEMISTRY FRONTIERS, 2016, 3 (07): : 804 - 808
  • [35] Copper-Catalyzed Nucleophilic Trifluoromethylation of Allylic Halides: A Simple Approach to Allylic Trifluoromethylation
    Miyake, Yoshihiro
    Ota, Shin-ichi
    Nishibayashi, Yoshiaki
    CHEMISTRY-A EUROPEAN JOURNAL, 2012, 18 (42) : 13255 - 13258
  • [36] Copper-Catalyzed Divergent Trifluoromethylation/Cyclization of Unactivated Alkenes
    Zheng, Jing
    Deng, Ziyang
    Zhang, Yan
    Cui, Sunliang
    ADVANCED SYNTHESIS & CATALYSIS, 2016, 358 (05) : 746 - 751
  • [37] Copper-catalyzed trifluoromethylation of alkenes with an electrophilic trifluoromethylating reagent
    Wang, Xiao-Ping
    Lin, Jin-Hong
    Zhang, Cheng-Pan
    Xiao, Ji-Chang
    Zheng, Xing
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2013, 9 : 2635 - 2640
  • [38] Copper-Catalyzed Trifluoromethylation of N,N-Dialkylhydrazones
    Pair, Etienne
    Monteiro, Nuno
    Bouyssi, Didier
    Baudoin, Olivier
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (20) : 5346 - 5349
  • [39] Copper-Catalyzed Trifluoromethylation of Polysubstituted Alkenes Assisted by Decarboxylation
    He, Zhengbiao
    Tan, Ping
    Hu, Jinbo
    ORGANIC LETTERS, 2016, 18 (01) : 72 - 75
  • [40] 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