The Heck reaction of electron-rich olefins with regiocontrol by hydrogen-bond donors

被引：108
作者：
Mo, Jun [1 ]
Xiao, Jianliang [1 ]
机构：
[1] Univ Liverpool, Dept Chem, Liverpool Ctr Mat & Catalysis, Liverpool L69 7ZD, Merseyside, England
来源：
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION | 2006年 / 45卷 / 25期
关键词：
Heck reaction; homogeneous catalysis; hydrogen bonding; ionic liquids; regioselectivity;
D O I：
10.1002/anie.200600799
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
No salt please: Halide scavengers AgOTf and TlOAc are not required for the Heck coupling of electron-rich olefins with aryl bromides and chlorides. Using ammonium additives, these reactions can be carried out in either an imidazolium ionic liquid or a common molecular solvent, thus furnishing 1,1′- disubstituted olefins in high yields with excellent regioselectivities. (Chemical Equation Presented). © 2006 Wiley-VCH Verlag GmbH & Co. KGaA.
引用
收藏
页码：4152 / 4157
页数：6
相关论文
共 46 条
  • [1] Anionic Pd(0) and Pd(II) intermediates in palladium-catalyzed Heck and cross-coupling reactions
    Amatore, C
    Jutand, A
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 2000, 33 (05) : 314 - 321
  • [2] Dioxygen-promoted regioselective oxidative Heck arylations of electron-rich olefins with arylboronic acids
    Andappan, MMS
    Nilsson, P
    von Schenck, H
    Larhed, M
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16) : 5212 - 5218
  • [3] [Anonymous], 2002, J ORGANOMET CHEM
  • [4] The development of palladium catalysts for C-C and C-heteroatom bond forming reactions of aryl chloride substrates
    Bedford, RB
    Cazin, CSJ
    Holder, D
    [J]. COORDINATION CHEMISTRY REVIEWS, 2004, 248 (21-24) : 2283 - 2321
  • [5] The heck reaction as a sharpening stone of palladium catalysis
    Beletskaya, IP
    Cheprakov, AV
    [J]. CHEMICAL REVIEWS, 2000, 100 (08) : 3009 - 3066
  • [6] Protected indanones by a Heck-Aldol annulation reaction
    Bengtson, A
    Larhed, M
    Hallberg, A
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 2002, 67 (16) : 5854 - 5856
  • [7] Brase S., 2004, METAL CATALYZED CROS, V1, P217
  • [8] ALPHA-REGIOSELECTIVITY IN PALLADIUM-CATALYZED ARYLATION OF ACYCLIC ENOL ETHERS
    CABRI, W
    CANDIANI, I
    BEDESCHI, A
    PENCO, S
    SANTI, R
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (05) : 1481 - 1486
  • [9] RECENT DEVELOPMENTS AND NEW PERSPECTIVES IN THE HECK REACTION
    CABRI, W
    CANDIANI, I
    [J]. ACCOUNTS OF CHEMICAL RESEARCH, 1995, 28 (01) : 2 - 7
  • [10] 1,10-PHENANTHROLINE DERIVATIVES - A NEW LIGAND CLASS IN THE HECK REACTION - MECHANISTIC ASPECTS
    CABRI, W
    CANDIANI, I
    BEDESCHI, A
    SANTI, R
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1993, 58 (26) : 7421 - 7426
12345