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
  • [31] Copper-catalyzed primary amination of arene C-H bond with hydroxylamine derivative
    Tan, Xiaobin
    Xiong, Wenfang
    Zhu, Baiyao
    Liu, Hongjian
    Wu, Wanqing
    Jiang, Huanfeng
    [J]. TETRAHEDRON LETTERS, 2023, 129
  • [32] Site-Selective Copper-Catalyzed Azidation of Benzylic C-H Bonds
    Suh, Sung-Eun
    Chen, Si-Jie
    Mandal, Mukunda
    Guzei, Ilia A.
    Cramer, Christopher J.
    Stahl, Shannon S.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (26) : 11388 - 11393
  • [33] Copper-catalyzed aerobic phosphonation of sp3 C-H bonds
    Basle, Olivier
    Li, Chao-Jun
    [J]. CHEMICAL COMMUNICATIONS, 2009, (27) : 4124 - 4126
  • [34] Site-Selective Copper-Catalyzed Azidation of Benzylic C-H Bonds
    Suh, Sung-Eun
    Chen, Si-Jie
    Mandal, Mukunda
    Guzei, Ilia A.
    Cramer, Christopher J.
    Stahl, Shannon S.
    [J]. Journal of the American Chemical Society, 2020, 142 (26): : 11388 - 11393
  • [35] Process development of febuxostat using palladium- and copper-catalyzed C-H arylation
    Komiyama, Masato
    Tsuchiya, Hideyoshi
    Teramoto, Mitsuru
    Yajima, Naoki
    Kurokawa, Masayuki
    Minamizono, Kunio
    Tsuchiya, Naoki
    Kato, Yoshiaki
    Sato, Yoshinori
    Dohi, Masahiko
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2019, 257
  • [36] Copper-Catalyzed Formal Dehydrogenative Coupling of Carbonyls with Polyfluoroarenes Leading to β-C-H Arylation
    Xie, Weilong
    Kim, Dongwook
    Chang, Sukbok
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2020, 142 (49) : 20588 - 20593
  • [37] Process Development of Febuxostat Using Palladium- and Copper-Catalyzed C-H Arylation
    Komiyama, Masato
    Tsuchiya, Hideyoshi
    Teramoto, Mitsuru
    Yajima, Naoki
    Kurokawa, Masayuki
    Minamizono, Kunio
    Tsuchiya, Naoki
    Kato, Yoshiaki
    Sato, Yoshinori
    Dohi, Masahiko
    [J]. ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2018, 22 (09) : 1306 - 1311
  • [38] Copper-Catalyzed Thiolation of the Di- or Trimethoxybenzene Arene C-H Bond with Disulfides
    Zhang, Shouhui
    Qian, Pengcheng
    Zhang, Manli
    Hu, Maolin
    Cheng, Jiang
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (19): : 6732 - 6735
  • [39] Copper-catalyzed arylation, vinylation and alkynylation of sp2 and sp3 C-H bonds with iodonium salts
    Liu, Chuan
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [40] Copper-Catalyzed Arylation of Remote C(sp3)-H Bonds in Carboxamides and Sulfonamides
    Li, Zhaodong
    Wang, Qian
    Zhu, Jieping
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (40) : 13288 - 13292
12345