Pd-catalyzed aerobic oxidative coupling of anilides with olefins through regioselective C-H bond activation

被引:87
作者
Wang, Jia-Rui [1 ]
Yang, Chu-Ting [1 ]
Liu, Lei [1 ]
Guo, Qing-Xiang [1 ]
机构
[1] Univ Sci & Technol China, Dept Chem, Anhua 230026, Peoples R China
基金
中国国家自然科学基金;
关键词
D O I
10.1016/j.tetlet.2007.06.001
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Pd-catalyzed aerobic oxidative coupling of anilides with olefins was achieved through selective C-H bond activation. Compared to the previous studies, not only did we successfully use molecular oxygen to replace the chemical oxidant, but we also obtained improved yields for a number of substrates. The reaction tended to give high yields for electron-rich anifides and electron-deficient olefins, with a best yield up to 91%. (c) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码:5449 / 5453
页数:5
相关论文
共 29 条
  • [1] Selective Pd-catalyzed oxidative coupling of anilides with olefins through C-H bond activation at room temperature
    Boele, MDK
    van Strijdonck, GPF
    de Vries, AHM
    Kamer, PCJ
    de Vries, JG
    van Leeuwen, PWNM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (08) : 1586 - 1587
  • [2] Palladium-catalyzed alkylation of sp2 and sp3 C-H bonds with methylboroxine and alkylboronic acids:: Two distinct C-H activation pathways
    Chen, Xiao
    Goodhue, Charles E.
    Yu, Jin-Quan
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2006, 128 (39) : 12634 - 12635
  • [3] Toward waste-free production of Heck products with a catalytic palladium system under oxygen
    Dams, M
    De Vos, DE
    Celen, S
    Jacobs, PA
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (30) : 3512 - 3515
  • [4] Palladium-catalyzed oxygenation of unactivated sp3 C-H bonds
    Desai, LV
    Hull, KL
    Sanford, MS
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2004, 126 (31) : 9542 - 9543
  • [5] The asymmetric intramolecular Heck reaction in natural product total synthesis
    Dounay, AB
    Overman, LE
    [J]. CHEMICAL REVIEWS, 2003, 103 (08) : 2945 - 2963
  • [6] Catalytic C-H bond functionalization with palladium(II):: Aerobic oxidative annulations of indoles
    Ferreira, EM
    Stoltz, BM
    [J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (32) : 9578 - 9579
  • [7] C-H bond functionalization in complex organic synthesis
    Godula, K
    Sames, D
    [J]. SCIENCE, 2006, 312 (5770) : 67 - 72
  • [8] ORTHO VINYLATION OF AROMATIC AMIDES VIA CYCLOPALLADATION COMPLEXES
    HORINO, H
    INOUE, N
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1981, 46 (22) : 4416 - 4422
  • [9] Palladium-catalysed oxidation of primary and secondary alcohols
    Muzart, J
    [J]. TETRAHEDRON, 2003, 59 (31) : 5789 - 5816
  • [10] Pd(OAc)2-catalyzed oxidation of alcohols to aldehydes and ketones by molecular oxygen
    Nishimura, T
    Onoue, T
    Ohe, K
    Uemura, S
    [J]. TETRAHEDRON LETTERS, 1998, 39 (33) : 6011 - 6014