Imidazolyl-Functionalized Ordered Mesoporous Polymer from Nanocasting as an Effective Support for Highly Dispersed Palladium Nanoparticles in the Heck Reaction

被引:23
作者
Karimi, Babak [1 ]
Marefat, Mohammad Reza [1 ]
Hasannia, Maliheh [1 ]
Akhavan, Pari Fadavi [1 ]
Mansouri, Fariborz [1 ]
Artelli, Zahra [1 ]
Mohammadi, Fariba [1 ]
Vali, Hojatollah [2 ,3 ]
机构
[1] Inst Adv Studies Basic Sci, Dept Chem, POB 45195-1159, Gava Zang 4513766731, Zanjan, Iran
[2] McGill Univ, Anat & Cell Biol, Montreal, PQ H3A 2A7, Canada
[3] McGill Univ, Facil Electron Microscopy Res, Montreal, PQ H3A 2A7, Canada
基金
美国国家科学基金会;
关键词
ionic liquids; mesoporous materials; nanoparticles; palladium; polymers; MIYAURA COUPLING REACTION; IONIC LIQUID CATALYSIS; HETEROGENEOUS CATALYSTS; POLY(IONIC LIQUID); POROUS MATERIALS; EFFICIENT; SUZUKI; COMPLEX; SILICA; PD/C;
D O I
10.1002/cctc.201600630
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
New imidazolyl-functionalized ordered mesoporous cross-linked polymers were prepared by the copolymerization of the ionic liquid 3-benzyl-1-vinyl-1H-imidazolium bromide with divinylbenzene as the cross-linker and azobisisobutyronitrile as the radical initiator in the presence of O-silylated SBA-15 as the hard template. The materials were characterized by N-2 adsorption-desorption analysis, TEM, thermogravimetric analysis, elemental analysis, and FTIR spectroscopy. The material, which benefits from the use of entrapped ionic liquid in the prepared polymer matrix in combination with its ordered mesoporous structure, is an excellent environment for the stabilization of highly dispersed Pd nanoparticles to result in a recyclable catalyst system with a significant activity in the Heck coupling reaction of aryl halides. The presence of well-distributed imidazolium functionalities in the polymeric framework might be responsible for the relatively uniform and nearly atomic scale distribution of Pd nanoparticles throughout the mesoporous structure and the prevention of Pd agglomeration during the reaction, which results in high durability, high stability, and good recycling characteristics of the catalyst. Although our catalyst system operates in a homogeneous pathway, it is also very stable and recyclable.
引用
收藏
页码:2508 / 2515
页数:8
相关论文
共 51 条
[1]   Palladium N-methylimidazolium supported complexes as efficient catalysts for the Heck reaction [J].
Altava, B ;
Burguete, MI ;
García-Verdugo, E ;
Karbass, N ;
Luis, SV ;
Puzary, A ;
Sans, V .
TETRAHEDRON LETTERS, 2006, 47 (14) :2311-2314
[2]  
[Anonymous], 2000, Green Chemistry, Challenging Perspectives
[3]  
[Anonymous], 2000, ANGEW CHEM, V112, P3926
[4]   Palladium(II) containing hydrotalcite as an efficient heterogeneous catalyst for Heck reaction [J].
Bennur, TH ;
Ramani, A ;
Bal, R ;
Chanda, BM ;
Sivasanker, S .
CATALYSIS COMMUNICATIONS, 2002, 3 (10) :493-496
[5]   Pd catalysis on dendronized solid support: Generation effects and the influence of the backbone structure [J].
Dahan, Adi ;
Portnoy, Moshe .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2007, 129 (18) :5860-5869
[6]   Impact of Pd-mordenite pretreatment on the heterogeneity of Heck catalysis [J].
Dams, M ;
Drijkoningen, L ;
De Vos, D ;
Jacobs, P .
CHEMICAL COMMUNICATIONS, 2002, (10) :1062-1063
[7]   Palladium-Containing Ionic Liquid-Based Ordered Mesoporous Organosilica: An Efficient and Reusable Catalyst for the Heck Reaction [J].
Elhamifar, Dawood ;
Karimi, Babak ;
Rastegar, Javad ;
Banakar, Mohammad Hossain .
CHEMCATCHEM, 2013, 5 (08) :2418-2424
[8]   Biodegradable ionic liquids - Part II. Effect of the anion and toxicology [J].
Garcia, MT ;
Gathergood, N ;
Scammells, PJ .
GREEN CHEMISTRY, 2005, 7 (01) :9-14
[9]   Protic ionic liquids: Properties and applications [J].
Greaves, Tamar L. ;
Drummond, Calum J. .
CHEMICAL REVIEWS, 2008, 108 (01) :206-237
[10]   Heterogeneous Heck reaction catalyzed by Pd/C in ionic liquid [J].
Hagiwara, H ;
Shimizu, Y ;
Hoshi, T ;
Suzuki, T ;
Ando, M ;
Ohkubo, K ;
Yokoyama, C .
TETRAHEDRON LETTERS, 2001, 42 (26) :4349-4351