Pd(II) supramolecular cage-catalyzed successive oxidative coupling: One-pot and regioselective synthesis of functionalized carbazoles from indoles

被引:3
|
作者
Wu, Xi-Ren [1 ,2 ]
Peng, He-Long [1 ]
Wei, Lian-Qiang [1 ]
Li, Li-Ping [1 ]
Yao, Su-Yang [1 ]
Ye, Bao-Hui [1 ]
机构
[1] Sun Yat Sen Univ, Sch Chem, MOE Key Lab Bioinorgan & Synthet Chem, Guangzhou 510275, Guangdong, Peoples R China
[2] Guangdong Med Univ, Sch Pharm, Dongguan 523808, Peoples R China
基金
中国国家自然科学基金;
关键词
Carbazole; Indole; Oxidative Heck reaction; Pd(II) supramolecular cage; C-H functionalization; ALKENYLATION; BENZANNULATION; EFFICIENT; ARENES;
D O I
10.1016/j.catcom.2019.02.023
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Carbazole is an important compound in pharmaceuticals and functional materials. A new Pd(II) supramolecular cage-catalyzed protocol for the synthesis of multifunctional carbazoles from indoles is described through regioselective successive oxidative Heck reactions. This new protocol is highly efficient, with a low Pd (2.4 mol%) catalyst loading and good compatibility for both N-H free and N-protected indole substrates. Moreover, it can be used to synthesize carbazoles with various functional groups by a one-pot two-step procedure. The excellent catalytic activity can be attributed to the distinct properties of the supramolecular cage structure in uniformly distributive and well-defined Pd(II) active centers on the cage surfaces.
引用
收藏
页码:12 / 18
页数:7
相关论文
共 26 条
  • [1] Palladium-Catalyzed Regioselective Oxidative Coupling of Indoles and One-Pot Synthesis of Acetoxylated Biindolyls
    Liang, Zuijun
    Zhao, Jinlong
    Zhang, Yuhong
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (01) : 170 - 177
  • [2] Palladium-Catalyzed Tandem Regioselective Oxidative Coupling from Indoles and Maleimides: One-Pot Synthesis of Indolopyrrolocarbazoles and Related Indolylmaleimides
    An, Yu-Long
    Yang, Zhen-Hua
    Zhang, He-Hui
    Zhao, Sheng-Yin
    ORGANIC LETTERS, 2016, 18 (02) : 152 - 155
  • [3] One-pot synthesis of carbazoles from indoles via a metal free benzannulation
    Kotha, Sambasivarao
    Aswar, Vikas R.
    Chinnam, Ajay Kumar
    TETRAHEDRON LETTERS, 2017, 58 (46) : 4360 - 4362
  • [4] A Tandem Approach to Functionalized Carbazoles from Indoles via Two Successive Regioselective Oxidative Heck Reactions Followed by Thermal Electrocyclization
    Laha, Joydey K.
    Dayal, Neetu
    ORGANIC LETTERS, 2015, 17 (19) : 4742 - 4745
  • [5] Palladium-Catalyzed Triple Successive C-H Functionalization: Direct Synthesis of Functionalized Carbazoles from Indoles
    Verma, Akhilesh K.
    Danodia, Abhinandan K.
    Saunthwal, Rakesh K.
    Patel, Monika
    Choudhary, Deepak
    ORGANIC LETTERS, 2015, 17 (15) : 3658 - 3661
  • [6] Pd(II)-Catalyzed C-H Activation of Styrylindoles: Short, Efficient, and Regioselective Synthesis of Functionalized Carbazoles
    Saunthwal, Rakesh K.
    Patel, Monika
    Kumar, Sonu
    Danodia, Abhinandan K.
    Verma, Akhilesh K.
    CHEMISTRY-A EUROPEAN JOURNAL, 2015, 21 (51) : 18601 - 18605
  • [7] Pd(II)-Catalyzed One-Pot, Three-Step Route for the Synthesis of Unsymmetrical Acridines
    Guo, Hai-Ming
    Mao, Run-Ze
    Wang, Qiao-Tian
    Niu, Hong-Ying
    Xie, Ming-Sheng
    Qu, Gui-Rong
    ORGANIC LETTERS, 2013, 15 (21) : 5460 - 5463
  • [8] One-pot copper-catalyzed synthesis of N-functionalized pyrazoles from boronic acids
    Beveridge, Ramsay E.
    Fernando, Dilinie
    Gerstenberger, Brian S.
    TETRAHEDRON LETTERS, 2010, 51 (38) : 5005 - 5008
  • [9] Synthesis of 8-heteroaryl nitroxoline analogues via one-pot sequential Pd-catalyzed coupling reactions
    Brodnik, Helena
    Pozgan, Franc
    Stefane, Bogdan
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2016, 14 (06) : 1969 - 1981
  • [10] One-pot gold-catalyzed synthesis of 3-silylethynyl indoles from unprotected o-alkynylanilines
    Brand, Jonathan P.
    Chevalley, Clara
    Waser, Jerome
    BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY, 2011, 7 : 565 - 569