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 50 条
  • [21] Dioxygen-promoted regioselective oxidative Heck arylations of electron-rich olefins with arylboronic acids
    Andappan, MMS
    Nilsson, P
    von Schenck, H
    Larhed, M
    JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (16): : 5212 - 5218
  • [22] HYDROGEN-BOND INTERACTIONS WITH SULFUR DONORS
    SHERRY, AD
    PURCELL, KF
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1972, 94 (06) : 1848 - &
  • [23] Hydrogen-Bond Donors in Drug Design
    Kenny, Peter W.
    JOURNAL OF MEDICINAL CHEMISTRY, 2022, 65 (21) : 14261 - 14275
  • [24] THE EFFECTIVENESS OF SOLVENTS AS HYDROGEN-BOND DONORS
    MARCUS, Y
    JOURNAL OF SOLUTION CHEMISTRY, 1991, 20 (09) : 929 - 944
  • [25] Ionic liquid-promoted, highly regioselective heck arylation of electron-rich olefins by aryl halides
    Mo, J
    Xu, LJ
    Xiao, JL
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2005, 127 (02) : 751 - 760
  • [26] PHOTOADDITION OF FURIL AND DIETHYLOXALATE TO ELECTRON-RICH OLEFINS
    ALJALAL, NA
    IJAM, MJ
    ALOMRAN, F
    GOPALAKRISHNAN, B
    JOURNAL OF PHOTOCHEMISTRY AND PHOTOBIOLOGY A-CHEMISTRY, 1991, 55 (03) : 339 - 345
  • [27] SYNTHESIS OF UNSYMMETRICALLY SUBSTITUTED ELECTRON-RICH OLEFINS
    BUZA, D
    KRASUSKI, W
    ROCZNIKI CHEMII, 1972, 46 (12): : 2377 - 2380
  • [28] SYNTHESIS OF UNSYMMETRICALLY SUBSTITUTED ELECTRON-RICH OLEFINS
    BUZA, D
    KRASUSKI, W
    ROCZNIKI CHEMII, 1975, 49 (12): : 2007 - 2016
  • [29] MOLECULAR-CONFORMATIONS OF ELECTRON-RICH OLEFINS
    HITCHCOCK, PB
    ACTA CRYSTALLOGRAPHICA SECTION A, 1978, 34 : S102 - S102
  • [30] DIELS-ALDER REACTION OF ALPHA-PYRONES WITH ELECTRON-RICH OLEFINS
    BEHRINGER, H
    HECKMAIER, P
    CHEMISCHE BERICHTE-RECUEIL, 1969, 102 (08): : 2835 - +
12345