The Heck reaction: mechanistic insights and novel ligands

被引:36
|
作者
Casey, M [1 ]
Lawless, J [1 ]
Shirran, C [1 ]
机构
[1] Natl Univ Ireland Univ Coll Dublin, Dept Chem, Dublin 4, Ireland
关键词
Heck reactions; palladium; phosphane; sulfane ligands; mechanism;
D O I
10.1016/S0277-5387(99)00398-8
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The kinetics of the Heck reaction of aryl iodides with methyl acrylate using phosphane ligands were studied. Triphenylphosphane strongly inhibited the reaction when used in excess over the Pd(0) precatalyst. The rate of reaction was found to be weakly dependent on the concentrations of both the aryl iodide and the alkene. The results indicate that the migratory insertion step is turnover limiting, with the oxidative addition to the aryl iodide being faster but not negligible. Phosphane sulfane hemilabile ligands were found to give good yields and good catalyst stability in Heck reactions. (C) 2000 Elsevier Science Ltd All rights reserved.
引用
收藏
页码:517 / 520
页数:4
相关论文
共 50 条
  • [1] The Heck reaction: Mechanistic investigations
    Herrmann, WA
    Reisinger, CP
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1997, 213 : 7 - INOR
  • [2] Mechanistic Insights into Palladium Leaching in Novel Pd/C-Catalyzed Boron-Heck Reaction of Arylboronic Acid
    Dighe, Mahesh G.
    Lonkar, Sachin L.
    Degani, Mariam S.
    SYNLETT, 2013, 24 (03) : 347 - 350
  • [3] The intermolecular asymmetric Heck reaction:: Mechanistic and computational studies
    Hii, KK
    Claridge, TDW
    Brown, JM
    Smith, A
    Deeth, RJ
    HELVETICA CHIMICA ACTA, 2001, 84 (10) : 3043 - 3056
  • [4] New Mechanistic Insights into the Copper-Free Heck-Cassar-Sonogashira Cross-Coupling Reaction
    Palladino, Chiara
    Fantoni, Tommaso
    Ferrazzano, Lucia
    Muzzi, Beatrice
    Ricci, Antonio
    Tolomelli, Alessandra
    Cabri, Walter
    ACS CATALYSIS, 2023, 13 (18): : 12048 - 12061
  • [5] The application of HETPHOX ligands to the intramolecular asymmetric Heck reaction
    Fitzpatrick, Martin O.
    Coyne, Anthony G.
    Guiry, Patrick J.
    SYNLETT, 2006, (18) : 3150 - 3154
  • [6] Diphenylphosphinoferrocenyloxazoline ligands for the intermolecular asymmetric Heck reaction.
    Guiry, PJ
    Kilroy, TG
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U105 - U105
  • [7] Diphenylphosphinooxazoline ligands in the asymmetric intramolecular Heck reaction.
    Guiry, PJ
    Kiely, D
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2001, 222 : U105 - U105
  • [8] The application of HETPHOX ligands to the asymmetric intermolecular heck reaction
    Kilroy, TG
    Cozzi, PG
    End, N
    Guiry, PJ
    SYNLETT, 2004, (01) : 106 - 110
  • [9] Pd(II) complexes of novel phosphine ligands: Synthesis, characterization, and catalytic activities on Heck reaction
    Altan, Orhan
    Serindag, Osman
    Sayin, Koray
    Karakas, Duran
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 2016, 191 (07) : 993 - 999
  • [10] Novel approach to the asymmetric Heck reaction
    Penn, Liza
    Shpruhman, Alina
    Gelman, Dmitri
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2007, 233