Palladium-catalyzed alkenation of thiophenes and furans by regioselective C-H bond functionalization

被引:42
|
作者
Zhao, Jinlong [1 ]
Huang, Lehao [1 ]
Cheng, Kai [1 ]
Zhang, Yuhong [1 ]
机构
[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Peoples R China
关键词
Palladium; Heterocycles; Thiophene; Alkenation; C-H activation; HECK REACTION; ARYL CHLORIDES; OLEFINATION; ARYLATION; ALKENYLATION; ACTIVATION; VINYLATION; ALDEHYDES; BENZENES; LIGANDS;
D O I
10.1016/j.tetlet.2009.03.124
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A palladium-catalyzed direct alkenation of thiophenes and furans has been developed in the presence of AgOAc and pyridine. A variety of olefinic substrates such as acrylates, acrylamides, and acrylonitrile can perform the direct oxidative coupling reactions with various thiophenes and furans to give the mono-alkenylated products in good yields. In most cases, the (E)-isomers were isolated as the major products. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码:2758 / 2761
页数:4
相关论文
共 50 条
  • [1] Palladium-Catalyzed Decarboxylative C-H Bond Arylation of Thiophenes
    Hu, Peng
    Zhang, Min
    Jie, Xiaoming
    Su, Weiping
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2012, 51 (01) : 227 - 231
  • [2] Palladium-Catalyzed Direct and Regioselective C-H Bond Functionalization/Oxidative Acetoxylation of Indoles
    Choy, Pui Ying
    Lau, Chak Po
    Kwong, Fuk Yee
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (01): : 80 - 84
  • [3] Palladium-Catalyzed Decarboxylative C-H Bond Arylation of Furans
    Pei, Kai
    Jie, Xiaoming
    Zhao, Huaiqing
    Su, Weiping
    [J]. EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (20) : 4230 - 4233
  • [4] Palladium-Catalyzed C-H Homocoupling of Furans and Thiophenes Using Oxygen as the Oxidant
    Li, Na-Na
    Zhang, Yan-Lei
    Mao, Shuai
    Gao, Ya-Ru
    Guo, Dong-Dong
    Wang, Yong-Qiang
    [J]. ORGANIC LETTERS, 2014, 16 (10) : 2732 - 2735
  • [5] Palladium-catalyzed C-H bond functionalization of amine derivatives
    Nadres, Enrico T.
    Daugulis, Olafs
    [J]. ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2012, 243
  • [6] Palladium-Catalyzed C-H Bond Functionalization with Arylsulfonyl Chlorides
    Zhao, Xiaodan
    Dimitrijevic, Elena
    Dong, Vy M.
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2009, 131 (10) : 3466 - +
  • [7] Palladium-Catalyzed Allylic C-H Bond Functionalization of Olefins
    Liu, Guosheng
    Wu, Yichen
    [J]. C-H ACTIVATION, 2010, 292 : 195 - 209
  • [8] Palladium-Catalyzed Highly Regioselective Arylation of Allylamines with Thiophenes and Furans
    Jiang, Zhen
    Zhang, Lingjuan
    Dong, Chaonan
    Cai, Zhongzheng
    Tang, Weijun
    Li, Huanrong
    Xu, Lijin
    Xiao, Jianliang
    [J]. ADVANCED SYNTHESIS & CATALYSIS, 2012, 354 (17) : 3225 - 3230
  • [9] Controlling Site Selectivity in Palladium-Catalyzed C-H Bond Functionalization
    Neufeldt, Sharon R.
    Sanford, Melanie S.
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2012, 45 (06) : 936 - 946
  • [10] Palladium-Catalyzed Regioselective C-S Bond Cleavage of Thiophenes
    Huang, Huanan
    Li, Jing
    Lescop, Christophe
    Duan, Zheng
    [J]. ORGANIC LETTERS, 2011, 13 (19) : 5252 - 5255