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
来源
JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 01期
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] One-pot synthesis of carbazoles by palladium-catalyzed N-arylation and oxidative coupling
    Watanabe, Toshiaki
    Ueda, Satoshi
    Inuki, Shinsuke
    Oishi, Shinya
    Fujii, Nobutaka
    Ohno, Hiroaki
    CHEMICAL COMMUNICATIONS, 2007, (43) : 4516 - 4518
  • [4] One-pot synthesis of carbazoles by palladium-catalyzed N-arylation and oxidative coupling
    Watanabe, Toshiaki
    Inuki, Shinsuke
    Ueda, Satoshi
    Oishi, Shinya
    Ohno, Hiroaki
    Fujii, Nobutaka
    DRUGS OF THE FUTURE, 2007, 32 : 136 - 137
  • [5] ONE-POT PALLADIUM-CATALYZED SYNTHESIS OF DIARYLALKYNES
    CARPITA, A
    LESSI, A
    ROSSI, R
    SYNTHESIS-STUTTGART, 1984, (07): : 571 - 572
  • [6] Tandem one-pot palladium-catalyzed reductive and oxidative coupling of benzene and chlorobenzene
    Mukhopadhyay, S
    Rothenberg, G
    Gitis, D
    Sasson, Y
    JOURNAL OF ORGANIC CHEMISTRY, 2000, 65 (10): : 3107 - 3110
  • [7] An Approach to One-Pot Regioselective Synthesis of Indenones through Palladium-Catalyzed Annulation in Water
    Ramesh, Karu
    Satyanarayana, Gedu
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2018, 2018 (30) : 4135 - 4146
  • [8] Palladium-Catalyzed Acylations: One-Pot Synthesis of Indenones
    Suchand, Basuli
    Satyanarayana, Gedu
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (01): : 372 - 381
  • [9] Palladium-Catalyzed Oxidative Synthesis of -Acetoxylated Enones from Alkynes
    Jiang, Tuo
    Quan, Xu
    Zhu, Can
    Andersson, Pher G.
    Backvall, Jan-E.
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (19) : 5824 - 5828
  • [10] 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