Palladium-Catalyzed Regioselective Oxidative Coupling of Indoles and One-Pot Synthesis of Acetoxylated Biindolyls

被引:151
|
作者
Liang, Zuijun [1 ]
Zhao, Jinlong [1 ]
Zhang, Yuhong [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China
关键词
DIRECT C-2 ARYLATION; H BOND ARYLATION; DIRECT FUNCTIONALIZATION; ROOM-TEMPERATURE; ARYL BROMIDES; C-O; ACTIVATION; ALDEHYDES; ACID; ALKENYLATION;
D O I
10.1021/jo902265s
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Mild conditions have been developed to achieve Pd-catalyzed homocoupling of indoles with excellent regioselectivity in the presence of Cu(OAc)(2)center dot H2O in DMSO at room temperature in high efficiency. This method provides a simple route to 2,3-biindolyls from the electron-rich to moderately electron-poor indoles. The reaction tolerates the bromide substitLient on indoles. In addition, a one-pot approach to C3-position acetoxylated biindolyls is realized via palladium catalysis by the use of AgOAc under oxygen atmosphere as oxidants.
引用
收藏
页码:170 / 177
页数:8
相关论文
共 50 条
  • [1] 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
  • [2] A palladium-catalyzed one-pot procedure for the regioselective dimerization and cyanation of indoles
    Kianmehr, Ebrahim
    Ghanbari, Mohammad
    Faghih, Nasser
    Rominger, Frank
    TETRAHEDRON LETTERS, 2012, 53 (15) : 1900 - 1904
  • [3] Utilizing Mor-DalPhos/Palladium-Catalyzed Monoarylation in the Multicomponent One-Pot Synthesis of Indoles
    Rotta-Loria, Nicolas L.
    Borzenko, Andrey
    Alsabeh, Pamela G.
    Lavery, Christopher B.
    Stradiotto, Mark
    ADVANCED SYNTHESIS & CATALYSIS, 2015, 357 (01) : 100 - 106
  • [4] One-Pot Palladium-Catalyzed Borrowing Hydrogen Synthesis of Thioethers
    Corma, Avelino
    Navas, Javier
    Rodenas, Tania
    Sabater, Maria J.
    CHEMISTRY-A EUROPEAN JOURNAL, 2013, 19 (51) : 17464 - 17471
  • [5] Pd(II) supramolecular cage-catalyzed successive oxidative coupling: One-pot and regioselective synthesis of functionalized carbazoles from indoles
    Wu, Xi-Ren
    Peng, He-Long
    Wei, Lian-Qiang
    Li, Li-Ping
    Yao, Su-Yang
    Ye, Bao-Hui
    CATALYSIS COMMUNICATIONS, 2019, 124 : 12 - 18
  • [6] Highly Regioselective Palladium-Catalyzed Oxidative Coupling of Indolizines and Vinylarenes via C-H Bond Cleavage
    Yang, Yuzhu
    Cheng, Kai
    Zhang, Yuhong
    ORGANIC LETTERS, 2009, 11 (24) : 5606 - 5609
  • [7] Palladium-Catalyzed Direct Acylation: One-Pot Relay Synthesis of Anthraquinones
    Suchand, Basuli
    Satyanarayana, Gedu
    SYNTHESIS-STUTTGART, 2019, 51 (03): : 769 - 779
  • [8] One-Pot Palladium-Catalyzed Carbonylative Sonogashira Coupling using Carbon Dioxide as Carbonyl Source
    Xiong, Wenfang
    Wu, Bowen
    Zhu, Baiyao
    Tan, Xiaobin
    Wang, Lu
    Wu, Wanqing
    Qi, Chaorong
    Jiang, Huanfeng
    CHEMCATCHEM, 2021, 13 (12) : 2843 - 2851
  • [9] Palladium-Catalyzed Regioselective Coupling Cyclohexenone into Indoles: Atom-Economic Synthesis of β-Indolyl Cyclohexenones and Derivatization Applications
    Wen, Zhen-Kang
    Wu, Xiao-Xue
    Bao, Wen-Kai
    Xiao, Jing-Jing
    Jian-Bin Chao
    ORGANIC LETTERS, 2020, 22 (12) : 4898 - 4902
  • [10] Palladium-Catalyzed One-Pot Conversion of Aldehydes to Amides
    Ali, Md Ashif
    Punniyamurthy, Tharmalingam
    ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (2-3) : 288 - 292