An extremely highly recoverable clay-supported Pd nanoparticle catalyst for solvent-free Heck-Mizoroki reactions

被引:23
作者
Martinez, Alejandro V.
Leal-Duaso, Alejandro
Garcia, Jose I.
Mayoral, Jose A. [1 ]
机构
[1] CSIC Univ Zaragoza, Fac Ciencias, ISQCH, E-50009 Zaragoza, Spain
关键词
CROSS-COUPLING REACTIONS; PALLADIUM NANOPARTICLES; SUZUKI-MIYAURA; METAL-CATALYSTS; LAPONITE CLAY; EFFICIENT; COMPLEXES; CHEMISTRY; MICROWAVE;
D O I
10.1039/c5ra10191c
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Palladium nanoparticles supported on LAPONITE (R), a synthetic clay, are shown to constitute a highly robust and stable catalytic system for Heck-Mizoroki reactions carried out under solventless conditions. Both the preparation and the use of the catalyst are straightforward, allowing easy separation of the reaction products in pure form. In the case of the reaction between butyl acrylate and iodobenzene, up to 50 catalyst cycles can be performed before observing a noticeable decrease in activity. After reactivation of the catalyst by calcination, it can be further used for at least an additional 25 reactions. The stability of the catalyst seems to be related to the electronic density of the reacting alkene, as illustrated by the results obtained using the same catalyst with other alkenes.
引用
收藏
页码:59983 / 59990
页数:8
相关论文
共 32 条
[1]   Non-conventional methodologies for transition-metal catalysed carbon-carbon coupling: a critical overview. Part 2: The Suzuki reaction [J].
Alonso, Francisco ;
Beletskaya, Irina P. ;
Yus, Miguel .
TETRAHEDRON, 2008, 64 (14) :3047-3101
[2]   Palladium metal catalysts in Heck C-C coupling reactions [J].
Biffis, A ;
Zecca, M ;
Basato, M .
JOURNAL OF MOLECULAR CATALYSIS A-CHEMICAL, 2001, 173 (1-2) :249-274
[3]   Analysis of the reactions used for the preparation of drug candidate molecules [J].
Carey, John S. ;
Laffan, David ;
Thomson, Colin ;
Williams, Mike T. .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2006, 4 (12) :2337-2347
[4]   A molecular Pd(II) complex incorporated into a MOF as a highly active single-site heterogeneous catalyst for C-Cl bond activation [J].
Chen, Liyu ;
Rangan, Sylvie ;
Li, Jing ;
Jiang, Huanfeng ;
Li, Yingwei .
GREEN CHEMISTRY, 2014, 16 (08) :3978-3985
[5]   The sonogashira reaction:: A booming methodology in synthetic organic chemistry [J].
Chinchilla, Rafael ;
Najera, Carmen .
CHEMICAL REVIEWS, 2007, 107 (03) :874-922
[6]   Layered double hydroxide supported nanopalladium catalyst for Heck-, Suzuki-, Sonogashira-, and Stille-type coupling reactions of chloroarenes [J].
Choudary, BM ;
Madhi, S ;
Chowdari, NS ;
Kantam, ML ;
Sreedhar, B .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (47) :14127-14136
[7]   Homogeneous and heterogeneous catalysis:: Bridging the gap through surface organometallic chemistry [J].
Copéret, C ;
Chabanas, M ;
Saint-Arroman, RP ;
Basset, JM .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2003, 42 (02) :156-181
[8]   Immobilized palladium on surface-modified Fe3O4/SiO2 nanoparticles: as a magnetically separable and stable recyclable high-performance catalyst for Suzuki and Heck cross-coupling reactions [J].
Du, Qingwei ;
Zhang, Wei ;
Ma, Hao ;
Zheng, Jia ;
Zhou, Bo ;
Li, Yiqun .
TETRAHEDRON, 2012, 68 (18) :3577-3584
[9]   Palladium nanoparticles supported on agarose-functionalized magnetic nanoparticles of Fe3O4 as a recyclable catalyst for C-C bond formation via Suzuki-Miyaura, Heck-Mizoroki and Sonogashira-Hagihara coupling reactions [J].
Firouzabadi, Habib ;
Iranpoor, Nasser ;
Gholinejad, Mohammad ;
Akbari, Samira ;
Jeddi, Neda .
RSC ADVANCES, 2014, 4 (33) :17060-17070
[10]   Atomically Dispersed Supported Metal Catalysts [J].
Flytzani-Stephanopoulos, Maria ;
Gates, Bruce C. .
ANNUAL REVIEW OF CHEMICAL AND BIOMOLECULAR ENGINEERING, VOL 3, 2012, 3 :545-574