Cobalt(II)-Catalyzed Oxidative C-H Arylation of Indoles and Boronic Acids

被引:90
|
作者
Zhu, Xinju [1 ]
Su, Jian-Hang [1 ]
Du, Cong [1 ]
Wang, Zheng-Long [1 ]
Ren, Chang-Jiu [1 ]
Niu, Jun-Long [1 ]
Song, Mao-Ping [1 ]
机构
[1] Zhengzhou Univ, Coll Chem & Mol Engn, Zhengzhou 450001, Peoples R China
基金
中国国家自然科学基金;
关键词
CATALYZED DIRECT ARYLATION; BOND ACTIVATION; SELECTIVE ARYLATION; COBALT CATALYSIS; ARYL BROMIDES; FUNCTIONALIZATIONS; CHLORIDES; (HETERO)ARENES; CARBOXAMIDES; ANNULATION;
D O I
10.1021/acs.orglett.6b03746
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Co(II)-catalyzed C-H C2 selective arylation of indoles with boronic acids through monodentate chelation assistance has been achieved for the first time. The unique features of this methodology include mild reaction conditions, highly C2 regioselectivity, and employment of a Grignard reagent-free catalytic system. A wide range of substrates, including unreactive arenes, are well tolerated, which enables the construction of the coupling products efficiently. This new strategy provides an alternative and versatile approach to construct biaryls using inexpensive cobalt catalyst.
引用
收藏
页码:596 / 599
页数:4
相关论文
共 50 条
  • [1] Rhodium-catalyzed regioselective direct C-H arylation of indoles with aryl boronic acids
    Wang, Liang
    Qu, Xing
    Li, Zhan
    Peng, Wang-Ming
    TETRAHEDRON LETTERS, 2015, 56 (24) : 3754 - 3757
  • [2] Cobalt-Catalyzed Enantioselective C-H Arylation of Indoles
    Jacob, Nicolas
    Zaid, Yassir
    Oliveira, Joao C. A.
    Ackermann, Lutz
    Wencel-Delord, Joanna
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2022, 144 (02) : 798 - 806
  • [3] Ruthenium(II)-Catalyzed C-H Arylation of Anilides with Boronic Acids, Borinic Acids and Potassium Trifluoroborates
    Hubrich, Jonathan
    Himmler, Thomas
    Rodefeld, Lars
    Ackermann, Lutz
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (2-3) : 474 - 480
  • [4] Thioketone-Directed Palladium(II)-Catalyzed C-H Arylation of Ferrocenes with Aryl Boronic Acids
    Cai, Zhong-Jian
    Liu, Chen-Xu
    Gu, Qing
    You, Shu-Li
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (05) : 1296 - 1299
  • [5] Cu-Catalyzed Oxidative Allylic C-H Arylation of Inexpensive Alkenes with (Hetero)Aryl Boronic Acids
    Pal, Suman
    Cotard, Marine
    Gerardin, Baptiste
    Hoarau, Christophe
    Schneider, Cedric
    ORGANIC LETTERS, 2021, 23 (08) : 3130 - 3135
  • [6] Copper-catalyzed oxidative sp3 C-H bond arylation with aryl boronic acids
    Basle, Olivier
    Li, Chao-Jun
    ORGANIC LETTERS, 2008, 10 (17) : 3661 - 3663
  • [7] Ruthenium(II)-Catalyzed Direct C-H Arylation of Indoles with Arylsilanes in Water
    Nareddy, Pradeep
    Jordan, Frank
    Szostak, Michal
    ORGANIC LETTERS, 2018, 20 (02) : 341 - 344
  • [8] Ru-Catalysed C-H Arylation of Indoles and Pyrroles with Boronic Acids: Scope and Mechanistic Studies
    Sollert, Carina
    Devaraj, Karthik
    Orthaber, Andreas
    Gates, Paul J.
    Pilarski, Lukasz T.
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (14) : 5380 - 5386
  • [9] Palladium catalyzed room temperature C-H arylation of indoles
    Larrosa, Igor
    Lebrasseur, Nathalie
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 238
  • [10] Thioamide directed iridium(i)-catalyzed C-H arylation of ferrocenes with aryl boronic acids
    Ban, Yan
    Wang, Yingxin
    Li, Hao
    Wang, Yan
    Li, Dianjun
    Yang, Jinhui
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (29) : 5759 - 5763