A new palladium complex supported on magnetic nanoparticles and applied as an catalyst in amination of aryl halides, Heck and Suzuki reactions

被引:57
|
作者
Ghorbani-Choghamarani, Arash [1 ]
Tahmasbi, Bahman [1 ]
Noori, Nourolah [1 ]
Ghafouri-nejad, Raziyeh [1 ]
机构
[1] Ilam Univ, Dept Chem, POB 69315516, Ilam, Iran
关键词
Magnetic nanoparticle; Palladium; Amination; Heck reaction; Suzuki reaction; CROSS-COUPLING REACTIONS; SILICA SULFURIC-ACID; IONIC LIQUID; EFFICIENT NANOCATALYST; MIYAURA REACTIONS; AQUEOUS AMMONIA; LIGAND; OXIDATION; BASE; PERFORMANCE;
D O I
10.1007/s13738-016-1020-x
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A simple, efficient and less expensive protocol for the phosphine-free C-C coupling reactions and synthesis of anilines in the presence of 2-aminobenzamide complex of palladium supported on Fe3O4 magnetic nanoparticles (Pd(0)-ABA-Fe3O4) has been reported. The Suzuki reaction was carried out in water or PEG using phenylboronic acid (PhB(OH)(2)) or sodium tetraphenyl borate (NaBPh4). Pd(0)-ABA-Fe3O4 has been found promising for Heck reaction of butyl acrylate, styrene or acrylonitrile with aryl halides (including Cl, Br and I). Also, Pd(0)-ABA-Fe3O4 has been found as efficient catalyst for the amination of aryl halides using aqueous ammonia. The products have been obtained in short reaction times and high yields. The catalyst was easily separated using an external magnet from the reaction mixture and reused for several runs without significant loss of its catalytic efficiency or palladium leaching. The leaching of catalyst has been examined by hot filtration and ICP-OES technique. The nanomagnetical catalyst was characterized by FTIR, TGA, XRD, VSM, TEM, SEM, EDS, DLS and ICP-OES techniques.
引用
收藏
页码:681 / 693
页数:13
相关论文
共 50 条
  • [31] 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
  • [32] Palladium-catalyzed amination of aryl halides: Mechanism and rational catalyst design
    Hartwig, JF
    SYNLETT, 1997, (04) : 329 - +
  • [33] Palladium supported on modified magnetic nanoparticles: a phosphine-free and heterogeneous catalyst for Suzuki and Stille reactions
    Ghorbani-Choghamarani, Arash
    Norouzi, Masoomeh
    APPLIED ORGANOMETALLIC CHEMISTRY, 2016, 30 (03) : 140 - 147
  • [34] A new catalyst system for the Heck reaction of unreactive aryl halides
    Reetz, MT
    Lohmer, G
    Schwickardi, R
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1998, 37 (04) : 481 - 483
  • [35] Tetraphosphine/palladium-catalyzed Heck reactions of aryl halides with disubstituted alkenes
    Kondolff, I
    Doucet, H
    Santelli, M
    TETRAHEDRON LETTERS, 2003, 44 (46) : 8487 - 8491
  • [36] Magnetic polymer nanocomposite-supported Pd: an efficient and reusable catalyst for the Heck and Suzuki reactions in water
    Wang, Dongfang
    Liu, Wendong
    Bian, Fengling
    Yu, Wei
    NEW JOURNAL OF CHEMISTRY, 2015, 39 (03) : 2052 - 2059
  • [37] Methyl Salicylate Functionalized Magnetic Chitosan Immobilized Palladium Nanoparticles: An Efficient Catalyst for the Suzuki and Heck Coupling Reactions in Water
    Hasan, Kamrul
    CHEMISTRYSELECT, 2020, 5 (23): : 7129 - 7140
  • [38] 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
  • [39] Palladium nanoparticles supported on functional ionic liquid modified magnetic nanoparticles as recyclable catalyst for room temperature Suzuki reaction
    Wang, Jiayi
    Xu, Beiling
    Sun, Haiyang
    Song, Gonghua
    TETRAHEDRON LETTERS, 2013, 54 (03) : 238 - 241
  • [40] Pd doped SiO2 nanoparticles: an efficient recyclable catalyst for Suzuki, Heck and Sonogashira reactions
    Kotadia, Deepali A.
    Patel, Urmila H.
    Gandhi, Sahaj
    Soni, Saurabh S.
    RSC ADVANCES, 2014, 4 (62): : 32826 - 32833