Palladium-catalyzed direct alkynylation of thiophenes with halosilylacetylenes

被引:2
|
作者
Kato, Hayate [1 ]
Tsukada, Naofumi [1 ]
机构
[1] Shizuoka Univ, Fac Sci, Dept Chem, Suruga Ku, 836 Ohya, Shizuoka 4228529, Japan
关键词
Palladium; Thiophene; Alkyne; Regioselective reaction; C-H functionalization; H BOND ARYLATION; COUPLING REACTIONS; TERMINAL ALKYNES; HETEROCYCLES; ACTIVATION; INDOLES; ACCESS; ACIDS; ARYL;
D O I
10.1016/j.tetlet.2021.152869
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Silylethynylthiophenes were obtained from palladium-catalyzed alkynylation of various thiophenes with 1-halo-2-silylacetylenes. The a-position of thiophenes was alkynylated with high regioselectivity. The terminal silyl groups of products could be replaced by several functional groups. (C) 2021 Elsevier Ltd. All rights reserved.
引用
收藏
页数:3
相关论文
共 50 条
  • [41] Palladium-Catalyzed Direct Cyclopropylation of Heterocycles
    Wu, Xiaojin
    Lei, Chuanhu
    Yue, Guizhou
    Zhou, Jianrong
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (33) : 9601 - 9605
  • [42] Direct Palladium-Catalyzed β-Arylation of Lactams
    Chen, Ming
    Liu, Feipeng
    Dong, Guangbin
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2018, 57 (14) : 3815 - 3819
  • [43] Palladium-Catalyzed Direct Arylation of Selenophene
    Rampon, Daniel S.
    Wessjohann, Ludger A.
    Schneider, Paulo H.
    JOURNAL OF ORGANIC CHEMISTRY, 2014, 79 (13): : 5987 - 5992
  • [44] Direct palladium-catalyzed arylation of cyclopropenes
    1600, American Chemical Society, Columbus, United States (127):
  • [45] Synthesis of 2-Acylthiophenes by Palladium-Catalyzed Addition of Thiophenes to Nitriles
    Jiang, Tao-Shan
    Wang, Guan-Wu
    ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (2-3) : 369 - 373
  • [46] Palladium-Catalyzed Decarboxylative C-H Bond Arylation of Thiophenes
    Hu, Peng
    Zhang, Min
    Jie, Xiaoming
    Su, Weiping
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (01) : 227 - 231
  • [47] Selectively substituted thiophenes and indoles by a tandem palladium-catalyzed multicomponent reaction
    Mitsudo, Koichi
    Thansandote, Praew
    Wilhelm, Thorsten
    Mariampillai, Brian
    Lautens, Mark
    ORGANIC LETTERS, 2006, 8 (18) : 3939 - 3942
  • [48] Palladium-Catalyzed Regioselective C-S Bond Cleavage of Thiophenes
    Huang, Huanan
    Li, Jing
    Lescop, Christophe
    Duan, Zheng
    ORGANIC LETTERS, 2011, 13 (19) : 5252 - 5255
  • [49] Palladium-catalyzed direct oxidative Heck-Cassar-Sonogashira type alkynylation of indoles with alkynes under oxygen
    Yang, Luo
    Zhao, Liang
    Li, Chao-Jun
    CHEMICAL COMMUNICATIONS, 2010, 46 (23) : 4184 - 4186
  • [50] Palladium-catalyzed alkynylation of aromatic amines via in situ formed trimethylammonium salts
    Liu, Long
    Yu, Wen-Qing
    Huang, Tianzeng
    Chen, Tieqiao
    TETRAHEDRON LETTERS, 2020, 61 (12)