Chitosan-Pd (II) Complex-Decorated Fe3O4 Nanoparticle as the Highly Effective and Magnetically Recyclable Catalyst for Suzuki and Heck Coupling Reactions

被引:12
作者
Fakhri, Akram [1 ]
Naghipour, Ali [1 ]
机构
[1] Ilam Univ, Dept Chem, Fac Sci, Ilam, Iran
关键词
cross-coupling reaction; Heck reaction; Suzuki reaction; chitosan-bound 5-bromosalicylaldehyde Pd complex; recoverable magnetic nanocatalyst; SUPPORTED PALLADIUM CATALYST; AEROBIC OXIDATION; PHOSPHINE-FREE; RECOVERABLE CATALYST; EFFICIENT CATALYSTS; ARYL CHLORIDES; LIGAND-FREE; PALLADACYCLES; CYCLOHEXANE; ORGANOSILICA;
D O I
10.1080/02603594.2017.1282351
中图分类号
O61 [无机化学];
学科分类号
070301 ; 081704 ;
摘要
A novel, recoverable magnetic nanocatalyst for Suzuki and Heck coupling reactions has been successfully prepared by immobilizing chitosan-bound 5-bromosalicylaldehyde Pd (II) complex on the surface of a Fe3O4 nanoparticle. Structure and composition of the solid catalyst were characterized by Fourier transform infrared (FT-IR), powder X-ray diffraction (XRD), scanning electron microscopy (SEM), inductively coupled plasma atomic emission analysis (ICP-AES), and thermogravimetric analysis (TGA). This nanocatalyst showed high catalytic activity for Suzuki coupling reactions of various aryl halides (I and Br, Cl) and phenylboronic acid in polyethyleneglycol (PEG 400) as an ecofriendly and non-poisonous media. The catalyst also exhibits high activity in a Heck reaction of iodo- and bromoarenes with butylacrylate. Moreover, the nanocatalyst could be separated easily from the reaction mixture by an external magnet and reused four times without obvious loss of catalytic activity.
引用
收藏
页码:201 / 218
页数:18
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共 62 条
  • [21] Catalysis of cyclohexane oxidation with air using various chitosan-supported metallotetraphenylporphyrin complexes
    Huang, Guan
    Guo, Can-Cheng
    Tang, Si-Si
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 261 (01) : 125 - 130
  • [22] Study on the heterogeneous degradation of chitosan with hydrogen peroxide under the catalysis of phosphotungstic acid
    Huang, Qun Zeng
    Wang, Shi Ming
    Huang, Jin Feng
    Zhuo, Li Hong
    Guo, Ying Chen
    [J]. CARBOHYDRATE POLYMERS, 2007, 68 (04) : 761 - 765
  • [23] Highly efficient aerobic oxidation of alcohols using a recoverable catalyst: The role of mesoporous channels of SBA-15 in stabilizing palladium nanoparticles
    Karimi, Babak
    Abedi, Sedigheh
    Clark, James H.
    Budarin, Vitaly
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (29) : 4776 - 4779
  • [24] Ordered Mesoporous Organosilica with Ionic-Liquid Framework: An Efficient and Reusable Support for the Palladium-Catalyzed Suzuki-Miyaura Coupling Reaction in Water
    Karimi, Babak
    Elhamifar, Dawood
    Clark, James H.
    Hunt, Andrew J.
    [J]. CHEMISTRY-A EUROPEAN JOURNAL, 2010, 16 (27) : 8047 - 8053
  • [25] Heterogeneous Pd/C-catalyzed ligand-free Suzuki-Miyaura coupling reaction using aryl boronic esters
    Kitamura, Yoshiaki
    Sakurai, Ai
    Udzu, Takahiro
    Maegawa, Tomohiro
    Monguchi, Yasunari
    Sajiki, Hironao
    [J]. TETRAHEDRON, 2007, 63 (43) : 10596 - 10602
  • [26] A highly efficient palladium nanocatalyst anchored on a magnetically functionalized polymer-nanotube support
    Ko, Sungrok
    Jang, Jyongsik
    [J]. ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2006, 45 (45) : 7564 - 7567
  • [27] Sulfonamide- and hydrazine-based palladium catalysts: Stable and efficient catalysts for C-C coupling reactions in aqueous medium
    Kumar, N. S. C. Ramesh
    Raj, I. Victor Paul
    Sudalai, A.
    [J]. JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2007, 269 (1-2) : 218 - 224
  • [28] Highly active and recyclable silica gel-supported palladium catalyst for mild cross-coupling reactions of unactivated heteroaryl chlorides
    Lee, Dong-Hwan
    Jung, Ji-Young
    Jin, Myung-Jong
    [J]. GREEN CHEMISTRY, 2010, 12 (11) : 2024 - 2029
  • [29] Study on synthesis of poly(GMA)-grafted Fe3O4/SiOX magnetic nanoparticles using atom transfer radical polymerization and their application for lipase immobilization
    Lei, Lin
    Liu, Xiao
    Li, Yanfeng
    Cui, Yanjun
    Yang, Yong
    Qin, Guorui
    [J]. MATERIALS CHEMISTRY AND PHYSICS, 2011, 125 (03) : 866 - 871
  • [30] Chitosan as a support for heterogeneous Pd catalysts in liquid phase catalysis
    Leonhardt, Silke E. S.
    Stolle, Achim
    Ondruschka, Bernd
    Cravotto, Giancarlo
    De Leo, Cristina
    Jandt, Klaus D.
    Keller, Thomas F.
    [J]. APPLIED CATALYSIS A-GENERAL, 2010, 379 (1-2) : 30 - 37