Metal-Organic Frameworks as Efficient Heterogeneous Catalysts for the Regioselective Ring Opening of Epoxides

被引:201
作者
Dhakshinamoorthy, Amarajothi [1 ,2 ]
Alvaro, Mercedes [1 ,2 ]
Garcia, Hermenegildo [1 ,2 ]
机构
[1] Univ Politecn Valencia, Inst Univ Tecnol Quim CSIC UPV, Valencia 46022, Spain
[2] Univ Politecn Valencia, Dept Quim, Valencia 46022, Spain
关键词
epoxides; green chemistry; heterogeneous catalysis; metal-organic frameworks; ring-opening reactions; EPOXIDATION; PROPENE;
D O I
10.1002/chem.201000588
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An iron-based metal organic framework, [Fe(BTC)] (BTC: 1,3,5-benzenetricarboxylate) is an efficient catalyst in the ring opening of styrene oxide with alcohols and aniline under mild reaction conditions. Out of the various alcohols tested for ring opening of styrene oxide, methanol was found to be the most reactive in terms of percentage conversion and reactivity. The rate of the ring-opening reaction of styrene oxide decreases as the size of the alcohol is increased, suggesting the location of active sites in micropores. [Fe(BTC)] was a truly heterogeneous catalyst and could be reused without loss of activity. The analogous compound [Cu(3)(BTC)(2)] was also found to be effective, although with somewhat lower activity than [Fe(BTC)]. The present heterogeneous protocol is compared with a homogeneous catalyst to give an insight into the reaction mechanism.
引用
收藏
页码:8530 / 8536
页数:7
相关论文
共 20 条
[1]   Probing the Lewis acidity and catalytic activity of the metal-organic framework [Cu3(btc)2] (BTC = benzene-1,3,5-tricarboxylate) [J].
Alaerts, Luc ;
Seguin, Etienne ;
Poelman, Hilde ;
Thibault-Starzyk, Frederic ;
Jacobs, Pierre A. ;
De Vos, Dirk E. .
CHEMISTRY-A EUROPEAN JOURNAL, 2006, 12 (28) :7353-7363
[2]   Enumeration of not-yet-synthesized zeolitic zinc imidazolate MOF networks: A topological and DFT approach [J].
Baburin, I. A. ;
Leoni, S. ;
Seifert, G. .
JOURNAL OF PHYSICAL CHEMISTRY B, 2008, 112 (31) :9437-9443
[3]   [Cu(H2btec)(bipy)]∞: a novel metal organic framework (MOF) as heterogeneous catalyst for the oxidation of olefins [J].
Brown, Kareen ;
Zolezzi, Santiago ;
Aguirre, Pedro ;
Venegas-Yazigi, Diego ;
Paredes-Garcia, Veronica ;
Baggio, Ricardo ;
Novak, Miguel A. ;
Spodine, Evgenia .
DALTON TRANSACTIONS, 2009, (08) :1422-1427
[4]   Metal organic frameworks as heterogeneous catalysts for the selective N-methylation of aromatic primary amines with dimethyl carbonate [J].
Dhakshinamoorthy, Amarajothi ;
Alvaro, Mercedes ;
Garcia, Hermenegildo .
APPLIED CATALYSIS A-GENERAL, 2010, 378 (01) :19-25
[5]   Claisen-Schmidt Condensation Catalyzed by Metal-Organic Frameworks [J].
Dhakshinamoorthy, Amarajothi ;
Alvaro, Mercedes ;
Garcia, Hermenegildo .
ADVANCED SYNTHESIS & CATALYSIS, 2010, 352 (04) :711-717
[6]   Metal organic frameworks as efficient heterogeneous catalysts for the oxidation of benzylic compounds with t-butylhydroperoxide [J].
Dhakshinamoorthy, Amarajothi ;
Alvaro, Mercedes ;
Garcia, Hermenegildo .
JOURNAL OF CATALYSIS, 2009, 267 (01) :1-4
[7]   Metal-Organic Frameworks (MOFs) as Heterogeneous Catalysts for the Chemoselective Reduction of Carbon-Carbon Multiple Bonds with Hydrazine [J].
Dhakshinamoorthy, Amarajothi ;
Alvaro, Mercedes ;
Garcia, Hermenegildo .
ADVANCED SYNTHESIS & CATALYSIS, 2009, 351 (14-15) :2271-2276
[8]   Metal-Organic Frameworks: Opportunities for Catalysis [J].
Farrusseng, David ;
Aguado, Sonia ;
Pinel, Catherine .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (41) :7502-7513
[9]   Large H2 storage capacity of a new polyhedron-based metal-organic framework with high thermal and hygroscopic stability [J].
Hong, Seunghee ;
Oh, Minhak ;
Park, Mira ;
Yoon, Ji Woong ;
Chang, Jong-San ;
Lah, Myoung Soo .
CHEMICAL COMMUNICATIONS, 2009, (36) :5397-5399
[10]   Synthesis and catalytic properties of MIL-100(Fe), an iron(III) carboxylate with large pores [J].
Horcajada, Patricia ;
Surble, Suzy ;
Serre, Christian ;
Hong, Do-Young ;
Seo, You-Kyong ;
Chang, Jong-San ;
Greneche, Jean-Marc ;
Margiolaki, Irene ;
Ferey, Gerard .
CHEMICAL COMMUNICATIONS, 2007, (27) :2820-2822