First efficient palladium-catalyzed Heck reactions of aryl bromides with alkyl methacrylate

被引:96
作者
Beller, M
Riermeier, TH
机构
[1] Anorganisch-chemisches Institut, 85747 Garching, TU München
关键词
D O I
10.1016/0040-4039(96)01442-6
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
An efficient palladium-catalyzed coupling reaction of aryl bromides with butyl methacrylate has been developed. Depending on the reaction conditions various amounts of butyl 3-aryl-2-methylpropenoate and butyl 3-aryl-2-methyliden-propenoate as well as double arylated products were produced. Superior turn over numbers up to 8300 and turn over frequencies up to 1000 h(-1) for Heck reactions of aryl bromides with methacrylic acid ester have been obtained for the first rime. Copyright (C) 1996 Elsevier Science Ltd
引用
收藏
页码:6535 / 6538
页数:4
相关论文
共 16 条
  • [1] PALLADACYCLES AS EFFICIENT CATALYSTS FOR ARYL COUPLING REACTIONS
    BELLER, M
    FISCHER, H
    HERRMANN, WA
    OFELE, K
    BROSSMER, C
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (17): : 1848 - 1849
  • [2] Beller M., 1995, ANGEW CHEM, V107, P1992
  • [3] BELLER M, 1996, IN PRESS PALLADIUM 5
  • [4] BELLER M, UNPUB
  • [5] FINE FEATHERS MAKE FINE BIRDS - THE HECK REACTION IN MODERN GARB
    DE MEIJERE, A
    MEYER, FE
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1994, 33 (23-24) : 2379 - 2411
  • [6] PALLADIUM-CATALYZED CONJUGATED DIENE SYNTHESIS FROM VINYLIC HALIDES AND OLEFINIC COMPOUNDS
    DIECK, HA
    HECK, RF
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1975, 40 (08) : 1083 - 1090
  • [7] Heck R.F., 1991, Comprehensive Organic Synthesis, V4, P833, DOI DOI 10.1016/B978-0-08-052349-1.00110-4
  • [8] Heck R.F., 1985, PALLADIUM REAGENTS O
  • [9] Herrmann W. A., 1995, ANGEW CHEM, V107, P1989
  • [10] PALLADACYCLES AS STRUCTURALLY DEFINED CATALYSTS FOR THE HECK OLEFINATION OF CHLOROARENES AND BROMOARENES
    HERRMANN, WA
    BROSSMER, C
    OFELE, K
    REISINGER, CP
    PRIERMEIER, T
    BELLER, M
    FISCHER, H
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1995, 34 (17): : 1844 - 1848