Copper-catalyzed direct C-H fluoroalkenylation of heteroarenes

被引：17
|
作者：
Rousee, Kevin
Schneider, Cedric
Bouillon, Jean-Philippe
Levacher, Vincent
Hoarau, Christophe [1 ]
Couve-Bonnaire, Samuel
Pannecoucke, Xavier
机构：
[1] Normandie Univ, COBRA, UMR 6014, F-76821 Mont St Aignan, France
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2016年 / 14卷 / 01期
关键词：
MEDIATED DIRECT ARYLATION; CARBON-CARBON BONDS; DIRECT ALKYNYLATION; PALLADIUM; FLUORINE; 1,1-DIBROMO-1-ALKENES; FUNCTIONALIZATION; HYDROGEN; 1,3,4-OXADIAZOLES; PHARMACEUTICALS;
D O I：
10.1039/c5ob02213d
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Copper-catalyzed direct C-H fluoroalkenylation of heterocycles using various gem-bromofluoroalkenes as electrophiles is reported. This efficient method offers step-economical, low-cost and stereocontrolled access to relevant heteroarylated monofluoroalkenes. The synthesis of fluorinated analogues of biomolecules and therapeutic agents for the treatment of Duchenne muscular dystrophy as application is reported.
引用
收藏
页码：353 / 357
页数：5
相关论文
共 50 条
  • [1] Palladium- and Copper-Catalyzed Stereocontrolled Direct C-H Fluoroalkenylation of Heteroarenes using gem-Bromofluoroalkenes
    Schneider, Cedric
    Masi, Daniela
    Couve-Bonnaire, Samuel
    Pannecoucke, Xavier
    Hoarau, Christophe
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (11) : 3246 - 3249
  • [2] Copper-Catalyzed Direct C-H Oxidative Trifluoromethylation of Heteroarenes
    Chu, Lingling
    Qing, Feng-Ling
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (02) : 1298 - 1304
  • [3] Copper(II)-Catalyzed Direct C-H Trifluoroethylation of Heteroarenes
    Dong, Lefeng
    Feng, Tingting
    Xiong, Dongdong
    Xu, Zhiping
    Cheng, Jiagao
    Xu, Xiaoyong
    Shao, Xusheng
    Li, Zhong
    ORGANIC LETTERS, 2022, 24 (10) : 1913 - 1917
  • [4] Copper-Catalyzed Electrophilic Amination of Heteroarenes via C-H Alumination
    Yoon, Hongju
    Lee, Yunmi
    JOURNAL OF ORGANIC CHEMISTRY, 2015, 80 (20): : 10244 - 10251
  • [5] Copper-Catalyzed Direct C-H Trifluoromethylation of Quinones
    Wang, Xi
    Ye, Yuxuan
    Ji, Guojing
    Xu, Yan
    Zhang, Songnan
    Feng, Jiajie
    Zhang, Yan
    Wang, Jianbo
    ORGANIC LETTERS, 2013, 15 (14) : 3730 - 3733
  • [6] Copper-catalyzed direct alkylation of heteroarenes
    Theunissen, Cedric
    Wang, Jianjun
    Evano, Gwilherm
    CHEMICAL SCIENCE, 2017, 8 (05) : 3465 - 3470
  • [7] Copper-Catalyzed Direct Perfluoroalkylation of Heteroarenes
    Baguia, Hajar
    Evano, Gwilherm
    CHEMISTRY-A EUROPEAN JOURNAL, 2022, 28 (06)
  • [8] Heterogeneously Catalyzed Direct C-H Thiolation of Heteroarenes
    Vasquez-Cespedes, Suhelen
    Ferry, Angelique
    Candish, Lisa
    Glorius, Frank
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (19) : 5772 - 5776
  • [9] Progress in Copper-Catalyzed Direct Arylation of Aromatic C-H Bonds
    Liu, Wei
    Bi, Yanlan
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (06) : 1041 - 1050
  • [10] Copper-Catalyzed Direct Arylselenation of Anilines by C-H Bond Cleavage
    Ricordi, Vanessa G.
    Thurow, Samuel
    Penteado, Filipe
    Schumacher, Ricardo F.
    Perin, Gelson
    Lenardao, Eder J.
    Alves, Diego
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (05) : 933 - 939
12345