Application of dimeric orthopalladate complex of homoveratrylamine as an efficient catalyst in the Heck cross-coupling reaction

被引:41
|
作者
Hajipour, Abdol R. [1 ,2 ]
Karami, Kazem [2 ]
Pirisedigh, Azadeh [1 ]
Ruoho, Arnold E. [1 ]
机构
[1] Univ Wisconsin, Dept Pharmacol, Sch Med, Madison, WI 53706 USA
[2] Isfahan Univ Technol, Dept Chem, Pharmaceut Res Lab, Esfahan 84156, Iran
关键词
Orthopalladate; Homoveratrylamine; Catalyst; Heck reaction; N-HETEROCYCLIC CARBENE; PHOSPHA-PALLADACYCLES; PALLADIUM COMPLEXES; CYCLOMETALATED COMPLEXES; MOLECULAR-STRUCTURE; ARYL CHLORIDES; PRIMARY AMINES; TRICYCLOHEXYLPHOSPHINE ADDUCTS; STRUCTURAL-CHARACTERIZATION; CYCLOPALLADATED COMPLEXES;
D O I
10.1016/j.jorganchem.2009.04.003
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
The [Pd{C6H2(CH2CH2NH2)-(OMe)(2),3,4} (mu-Br)](2) complex of homoveratrylamine was synthesized and its application in the Heck coupling reaction was studied. This complex had been demonstrated to be active and efficient catalyst for the Heck reaction of aryl iodides, bromides and even chlorides. The cross-coupled products were produced in excellent yields in a short reaction time using catalytic amounts of [Pd{C6H2(CH2CH2NH2)-(OMe)(2),3,4} (mu-Br)](2) complex in N-methyl-2-pyrrolidinone (NMP at 130 degrees C). (C) 2009 Elsevier B.V. All rights reserved.
引用
收藏
页码:2548 / 2554
页数:7
相关论文
共 50 条
  • [21] The Heck-Mizoroki cross-coupling reaction: a mechanistic perspective
    Knowles, Jonathan P.
    Whiting, Andrew
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2007, 5 (01) : 31 - 44
  • [22] Synthesis of cinnamyl substituted dihydrofuranones by the Heck cross-coupling reaction
    Ghochikyan, Tariel V.
    Vardanyan, Arpine S.
    Samvelyan, Melanya A.
    Galstyan, Armen S.
    Langer, Peter
    MENDELEEV COMMUNICATIONS, 2020, 30 (02) : 236 - 237
  • [23] Highly active PdCu/graphene catalyst for an efficient Suzuki cross-coupling reaction
    M., Xiaojing
    Gao, Lingfeng
    Weng, Zhentao
    Yang, Hua
    Sun, Xu
    NEW JOURNAL OF CHEMISTRY, 2020, 44 (47) : 20525 - 20529
  • [24] Pd nanoparticles embedded into MOF 808: An efficient and reusable catalyst for Sonogashira and Heck cross-coupling reactions
    Zhao, Zesheng
    Wang, Jie
    Zhang, Xiaoli
    Lin, Taofeng
    Ren, Jianwei
    Pang, Wan
    TETRAHEDRON LETTERS, 2022, 100
  • [25] A highly efficient palladium complex supported on MCM-41 nanocatalyst for Mizoroki–Heck and Suzuki–Miyaura cross-coupling reaction
    Mohsen Nikoorazm
    Maryam Khanmoradi
    Zahra Abdi
    Journal of the Iranian Chemical Society, 2020, 17 : 2577 - 2585
  • [26] Palladium-Schiff Base Complex Immobilized Covalently on Magnetic Nanoparticles as an Efficient and Recyclable Catalyst for Heck and Suzuki Cross-Coupling Reactions
    Sobhani, Sara
    Falatooni, Zahra Mesbah
    Asadi, Solmaz
    Honarmand, Moones
    CATALYSIS LETTERS, 2016, 146 (01) : 255 - 268
  • [27] Palladium-Schiff Base Complex Immobilized Covalently on Magnetic Nanoparticles as an Efficient and Recyclable Catalyst for Heck and Suzuki Cross-Coupling Reactions
    Sara Sobhani
    Zahra Mesbah Falatooni
    Solmaz Asadi
    Moones Honarmand
    Catalysis Letters, 2016, 146 : 255 - 268
  • [28] Synthesis of polystyrene-supported Pd(II)-NHC complex derived from theophylline as an efficient and reusable heterogeneous catalyst for the Heck-Matsuda cross-coupling reaction
    Mohammadi, Elmira
    Movassagh, Barahman
    JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2016, 418 : 158 - 167
  • [29] Efficient preparation and application of palladium loaded montmorillonite as a reusable and effective heterogeneous catalyst for Suzuki cross-coupling reaction
    Tian, Li
    Yanjun, Liu
    Feng-Shou, Liu
    APPLIED CLAY SCIENCE, 2017, 136 : 18 - 25
  • [30] An efficient palladium catalyzed Mizoroki-Heck cross-coupling in water
    Jadhav, Sanjay N.
    Rode, Chandrashekhar V.
    GREEN CHEMISTRY, 2017, 19 (24) : 5958 - 5970