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
  • [21] Mechanistic insights into the stereocontrolling non-covalent π interactions in Pd-catalyzed redox-relay Heck arylation reaction
    Hu, Xiaoxiao
    Shen, Boming
    Zhang, Jin
    Yu, Peiyuan
    CHEMICAL COMMUNICATIONS, 2025, 61 (27) : 5178 - 5181
  • [22] Mechanistic Insights on the Selectivity of the Tandem Heck-Ring-Opening of Cyclopropyldiol Derivatives
    Cohen, Anthony
    Kaushansky, Alexander
    Marek, Ilan
    JACS AU, 2022, 2 (03): : 687 - 696
  • [23] Insights into the Heck reaction with PCP pincer palladium(II) complexes
    Eberhard, MR
    ORGANIC LETTERS, 2004, 6 (13) : 2125 - 2128
  • [24] The Synthesis of New HetPHOX Ligands and Their Application to the Intermolecular Asymmetric Heck Reaction
    Fitzpatrick, Martin O.
    Muller-Bunz, Helge
    Guiry, Patrick J.
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2009, 2009 (12) : 1889 - 1895
  • [25] A dramatic switch of enantioselectivity in asymmetric heck reaction by benzylic substituents of ligands
    Wu, Wen-Qiong
    Peng, Qian
    Dong, Da-Xuan
    Hou, Xue-Long
    Wu, Yun-Dong
    Journal of the American Chemical Society, 2008, 130 (30): : 9717 - 9725
  • [26] Phosphite-oxazole/imidazole ligands in asymmetric intermolecular Heck reaction
    Mazuela, Javier
    Tolstoy, Paivi
    Pamies, Oscar
    Andersson, Pher G.
    Dieguez, Montserrat
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2011, 9 (03) : 941 - 946
  • [27] Highly active Pd(II) catalysts with pyridylbenzoimidazole ligands for the Heck reaction
    Chen, Weixuan
    Xi, Chanjuan
    Wu, Yongwei
    JOURNAL OF ORGANOMETALLIC CHEMISTRY, 2007, 692 (20) : 4381 - 4388
  • [28] Amino acid-modified cyclodextrins as ligands for Heck reaction in water
    Shibing Hong
    Mengyan Liu
    Yuan Shuai
    Zhuyi Wang
    Liyi Shi
    Wei Deng
    Journal of Inclusion Phenomena and Macrocyclic Chemistry, 2014, 80 : 443 - 448
  • [29] A dramatic switch of enantioselectivity in asymmetric Heck reaction by benzylic substituents of ligands
    Wu, Wen-Qiong
    Peng, Qian
    Dong, Da-Xuan
    Hou, Xue-Long
    Wu, Yun-Dong
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (30) : 9717 - 9725
  • [30] Amino acid-modified cyclodextrins as ligands for Heck reaction in water
    Hong, Shibing
    Liu, Mengyan
    Shuai, Yuan
    Wang, Zhuyi
    Shi, Liyi
    Deng, Wei
    JOURNAL OF INCLUSION PHENOMENA AND MACROCYCLIC CHEMISTRY, 2014, 80 (3-4) : 443 - 448