Superparamagnetic polymer composite microspheres supported Schiff base palladium complex: An efficient and reusable catalyst for the Suzuki coupling reactions

被引:67
作者
Yuan, Dingzhong [1 ,2 ]
Chen, Long [2 ]
Yuan, Ligang [2 ]
Liao, Shijun [2 ]
Yang, Mengmei [2 ]
Zhang, Qinghua [2 ]
机构
[1] E China Inst Technol, State Key Lab Breeding Base Nucl Resources & Envi, Nanchang 330013, Peoples R China
[2] E China Inst Technol, Dept Mat Sci & Engn, Nanchang 330013, Peoples R China
关键词
Superparamagnetic polymer composite microspheres; Suzuki coupling reactions; Palladium; Heterogeneous catalyst; MESOPOROUS SILICA; HETEROGENEOUS CATALYSIS; MAGNETIC NANOPARTICLE; CARBOCYCLIC CARBENE; PD(II) COMPLEXES; AQUEOUS SOLVENTS; ARYL CHLORIDES; GRAPHENE OXIDE; MIZOROKI-HECK; 3-PHASE TEST;
D O I
10.1016/j.cej.2015.10.081
中图分类号
X [环境科学、安全科学];
学科分类号
08 ; 0830 ;
摘要
Superparamagnetic polymer composite microspheres Fe3O4/P(GMA-AA-MMA) prepared by soap free emulsion polymerization were used to support Schiff base palladium complex. Fourier transform infrared (FTIR), X-ray diffraction (XRD), transmission electron microscopy (TEM), vibrating sample magnetometer (VSM), X-ray photoelectronic spectrography (XPS) and thermal gravity (TG) studies have been used to characterize the supported magnetic Schiff base catalyst. The magnetic catalyst could provide excellent reactivity in the Suzuki coupling reactions of aryl halides with phenylboronic acids under mild condition. Meanwhile, the supported magnetic catalyst acted as a true heterogeneous catalyst in the Suzuki coupling reactions. Furthermore, the novel catalyst could be conveniently recovered by an external magnet and reused at least seven times without significant loss of its catalytic activity or Pd leaching. (C) 2015 Elsevier B.V. All rights reserved.
引用
收藏
页码:241 / 251
页数:11
相关论文
共 51 条
[1]   General catalysts for the Suzuki-Miyaura and Sonogashira coupling reactions of aryl chlorides and for the coupling of challenging substrate combinations in water [J].
Anderson, KW ;
Buchwald, SL .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2005, 44 (38) :6173-6177
[2]   Efficient, Selective, and Recyclable Palladium Catalysts in Carbon-Carbon Coupling Reactions [J].
Arpad Molnar .
CHEMICAL REVIEWS, 2011, 111 (03) :2251-2320
[3]   Biguanide/Pd(OAc)2 immobilized on magnetic nanoparticle as a recyclable catalyst for the heterogeneous Suzuki reaction in aqueous media [J].
Beygzadeh, M. ;
Alizadeh, A. ;
Khodaei, M. M. ;
Kordestani, D. .
CATALYSIS COMMUNICATIONS, 2013, 32 :86-91
[4]   Anchoring of palladium(II) in chemically modified mesoporous silica: An efficient heterogeneous catalyst for Suzuki cross-coupling reaction [J].
Bhunia, Susmita ;
Sen, Rupam ;
Koner, Subratanath .
INORGANICA CHIMICA ACTA, 2010, 363 (14) :3993-3999
[5]  
Bohade S.R., 2008, TETRAHEDRON LETT, V49, P3423
[6]  
Borhade SR, 2010, INDIAN J CHEM B, V49, P565
[7]   Suzuki Reaction of Aryl Bromides Using a Phosphine-Free Magnetic Nanoparticle-Supported Palladium Catalyst [J].
Bui, Nghia T. ;
Dang, Trung B. ;
Le, Ha V. ;
Phan, Nam T. S. .
CHINESE JOURNAL OF CATALYSIS, 2011, 32 (11) :1667-1676
[8]   Three-component terpolymers of glycidyl methacrylate with good swelliniz characteristics [J].
Bukowska, Agnieszka ;
Bukowski, Wiktor ;
Noworol, Jaroslaw .
JOURNAL OF APPLIED POLYMER SCIENCE, 2007, 106 (06) :3800-3807
[9]   Polymer-Supported Electron-Rich Oxime Palladacycle as an Efficient Heterogeneous Catalyst for the Suzuki Coupling Reaction [J].
Cho, Hong-Jun ;
Jung, Sungwon ;
Kong, Saerom ;
Park, Sung-Jun ;
Lee, Sang-Myung ;
Lee, Yoon-Sik .
ADVANCED SYNTHESIS & CATALYSIS, 2014, 356 (05) :1056-1064
[10]   A new functionalized mesoporous matrix supported Pd(II)-Schiff base complex: an efficient catalyst for the Suzuki-Miyaura coupling reaction [J].
Dhara, Koushik ;
Sarkar, Krishanu ;
Srimani, Dipankar ;
Saha, Subrata Kumar ;
Chattopadhyay, Pabitra ;
Bhaumik, Asim .
DALTON TRANSACTIONS, 2010, 39 (28) :6395-6402