A General Method for Copper-Catalyzed Arylation of Arene C-H Bonds

被引：508
|
作者：
Do, Hien-Ouang [1 ]
Khan, Rana M. Kashif [1 ]
Daugulis, Olafs [1 ]
机构：
[1] Univ Houston, Dept Chem, Houston, TX 77204 USA
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 2008年 / 130卷 / 45期
关键词：
D O I：
10.1021/ja805688p
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
A general method for copper-catalyzed arylation of sp(2) C-H bonds with pK(a)'s below 35 has been developed. The method employs aryl halide as the coupling partner, lithium alkoxide or K3PO4 base, and DMF, DMPU, or mixed DMF/xylenes solvent. A variety of electron-rich and electron-poor heterocycles such as azoles, caffeine, thiophenes, benzofuran, pyridine oxides, pyridazine, and pyrimidine can be arylated. Furthermore, electron-poor arenes possessing at least two electron-withdrawing groups on a benzene ring can also be arylated. Two arylcopper-phenanthroline complex intermediates were independently synthesized.
引用
收藏
页码：15185 / 15192
页数：8
相关论文
共 50 条
  • [1] Copper-catalyzed arylation of heterocycle C-H bonds
    Do, Hien-Quang
    Daugulis, Olafs
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (41) : 12404 - +
  • [2] Copper-Catalyzed Etherification of Arene C-H Bonds
    Roane, James
    Daugulis, Olafs
    [J]. ORGANIC LETTERS, 2013, 15 (22) : 5842 - 5845
  • [3] Copper-catalyzed arylation and alkenylation of polyfluoroarene C-H bonds
    Do, Hien-Quang
    Daugulis, Olafs
    [J]. Journal of the American Chemical Society, 2008, 130 (04): : 1128 - 1129
  • [4] Copper-catalyzed arylation and alkenylation of polyfluoroarene C-H bonds
    Do, Hien-Quang
    Daugulis, Olafs
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (04) : 1128 - +
  • [5] Progress in Copper-Catalyzed Direct Arylation of Aromatic C-H Bonds
    Liu, Wei
    Bi, Yanlan
    [J]. CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2012, 32 (06) : 1041 - 1050
  • [6] DFT Studies on Copper-Catalyzed Arylation of Aromatic C-H Bonds
    Wang, Meiyan
    Fan, Ting
    Lin, Zhenyang
    [J]. ORGANOMETALLICS, 2012, 31 (02) : 560 - 569
  • [7] Enantioselective Arylation of Benzylic C-H Bonds by Copper-Catalyzed Radical Relay
    Zhang, Wen
    Wu, Lianqian
    Chen, Pinhong
    Liu, Guosheng
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2019, 58 (19) : 6425 - 6429
  • [8] Copper-Catalyzed Arylation of Benzylic C-H bonds with Alkylarenes as the Limiting Reagents
    Zhang, Wen
    Chen, Pinhong
    Liu, Guosheng
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2017, 139 (23) : 7709 - 7712
  • [9] Copper-Catalyzed Arylation of Benzylic C-H bonds with Alkylarenes as the Limiting Reagents
    [J]. Liu, Guosheng (gliu@mail.sioc.ac.cn), 1600, American Chemical Society (139):
  • [10] A GENERAL METHOD FOR COPPER-CATALYZED ARYLATION OF ACIDIC ARENE C-H BONDS. PREPARATION OF 2-CHLORO-5-(3-METHYLPHENYL)-THIOPHENE
    Alvarado, Joseph
    Do, Hien-Quang
    Daugulis, Olafs
    Marsden, Peter C.
    Ellman, Jonathan A.
    [J]. ORGANIC SYNTHESES, 2010, 87 : 184 - +
12345