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
  • [1] Hydrogen-bond-directed catalysis: Faster, regioselective and cleaner Heck arylation of electron-rich olefins in alcohols
    Hyder, Zeynab
    Ruan, Jiwu
    Xiao, Jianliang
    CHEMISTRY-A EUROPEAN JOURNAL, 2008, 14 (18) : 5555 - 5566
  • [2] "Hydridic Hydrogen-Bond Donors" Are Not Hydrogen-Bond Donors
    Santos, Lucas de Azevedo
    Vermeeren, Pascal
    Bickelhaupt, F. Matthias
    Guerra, Celia Fonseca
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2024, 146 (37) : 25701 - 25709
  • [3] Palladium-catalyzed highly regioselective Heck reaction of aryl nonaflates with electron-rich olefins
    Dan Xu Zhi Hua Liu Wei Jun Tang Jun Mo Li Jin Xu~* Department of Chemistry
    Chinese Chemical Letters, 2008, (09) : 1017 - 1020
  • [4] Palladium-catalyzed highly regioselective Heck reaction of aryl nonaflates with electron-rich olefins
    Xu, Dan
    Liu, Zhi Hua
    Tang, Wei Jun
    Mo, Jun
    Xu, Li Jin
    CHINESE CHEMICAL LETTERS, 2008, 19 (09) : 1017 - 1020
  • [5] Regioselective Heck couplings of α,β-unsaturated tosylates and mesylates with electron-rich olefins
    Hansen, AL
    Skrydstrup, T
    ORGANIC LETTERS, 2005, 7 (25) : 5585 - 5587
  • [6] Mild and Efficient Nickel-Catalyzed Heck Reactions with Electron-Rich Olefins
    Gogsig, Thomas M.
    Kleimark, Jonatan
    Lill, Sten O. Nilsson
    Korsager, Signe
    Lindhardt, Anders T.
    Norrby, Per-Ola
    Skrydstrup, Troels
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2012, 134 (01) : 443 - 452
  • [7] REACTIVITY OF ELECTRON-RICH OLEFINS .7. SYNTHESIS OF PHENOLALDEHYDES WITH ELECTRON-RICH OLEFINS
    HOCKER, J
    GIESECKE, H
    MERTEN, R
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1976, 15 (03): : 169 - 170
  • [8] REACTIONS OF ELECTRON-RICH OLEFINS
    HOFFMANN, RW
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1968, 7 (10) : 754 - &
  • [9] From α-Arylation of Olefins to Acylation with Aldehydes: A Journey in Regiocontrol of the Heck Reaction
    Ruan, Jiwu
    Xiao, Jianliang
    ACCOUNTS OF CHEMICAL RESEARCH, 2011, 44 (08) : 614 - 626
  • [10] ADDITION-ELIMINATION REACTION IN THE TRIFLUOROACETYLATION OF ELECTRON-RICH OLEFINS
    MORIGUCHI, T
    ENDO, T
    TAKATA, T
    JOURNAL OF ORGANIC CHEMISTRY, 1995, 60 (11): : 3523 - 3528
12345