Hoveyda-Grubbs type metathesis catalyst immobilized on mesoporous molecular sieves MCM-41 and SBA-15

被引：31

作者：

Balcar, Hynek ^{[1
]}

Shinde, Tushar ^{[1
]}

Zilkova, Nadezda ^{[1
]}

Bastl, Zdenek ^{[1
]}

机构：

[1] AS CR, J Heyrovsky Inst Phys Chem, Vvi, Prague 18223 8, Czech Republic

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2011年 / 7卷

关键词：

alkene metathesis; catalyst immobilization; hybrid catalysts; mesoporous molecular sieves; Ru-alkylidene complexes; RING-CLOSING METATHESIS; ELECTRON-WITHDRAWING LIGANDS; OLEFIN METATHESIS; RUTHENIUM CATALYSTS; REACTIVITY; STRATEGIES; CARBENES; SUPPORT; GEL;

D O I：

10.3762/bjoc.7.4

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A commercially available Hoveyda-Grubbs type catalyst (RC303 Zhannan Pharma) was immobilized on mesoporous molecular sieves MCM-41 and on SBA-15 by direct interaction with the sieve wall surface. The immobilized catalysts exhibited high activity and nearly 100% selectivity in several types of alkene metathesis reactions. Ru leaching was found to depend on the substrate and solvent used (the lowest leaching was found for ring-closing metathesis of 1,7-octadiene in cyclohexane - 0.04% of catalyst Ru content). Results of XPS, UV-vis and NMR spectroscopy showed that at least 76% of the Ru content was bound to the support surface non-covalently and could be removed from the catalyst by washing with THF.

引用

页码：22 / 28

页数：7

共 31 条

[1]

BALCAR H, 1984, COLLECT CZECH CHEM C, V49, P1736, DOI 10.1135/cccc19841736

[2] A NEW FAMILY OF MESOPOROUS MOLECULAR-SIEVES PREPARED WITH LIQUID-CRYSTAL TEMPLATES [J].

BECK, JS ;

VARTULI, JC ;

ROTH, WJ ;

LEONOWICZ, ME ;

KRESGE, CT ;

SCHMITT, KD ;

CHU, CTW ;

OLSON, DH ;

SHEPPARD, EW ;

MCCULLEN, SB ;

HIGGINS, JB ;

SCHLENKER, JL .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1992, 114 (27) :10834-10843

[3] SBA-15 Immobilized Ruthenium Carbenes as Catalysts for Ring Closing Metathesis and Ring Opening Metathesis Polymerization [J].

Bek, David ;

Zilkova, Nadezda ;

Dedecek, Jiri ;

Sedlacek, Jan ;

Balcar, Hynek .

TOPICS IN CATALYSIS, 2010, 53 (3-4) :200-209

[4] Polymer-Supported Well-Defined Metathesis Catalysts [J].

Buchmeiser, Michael R. .

CHEMICAL REVIEWS, 2009, 109 (02) :303-321

[5] Design and synthesis of supported catalysts on a molecular base [J].

Buchmeiser, MR .

CATALYSIS TODAY, 2005, 105 (3-4) :612-617

[6] Aqueous Olefin Metathesis [J].

Burtscher, Daniel ;

Grela, Karol .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2009, 48 (03) :442-454

[7] Sustainable concepts in olefin metathesis [J].

Clavier, Herve ;

Grela, Karo ;

Kirschning, Andreas ;

Mauduit, Marc ;

Nalon, Steven P. .

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2007, 46 (36) :6786-6801

[8] Strategies to immobilize well-defined olefin metathesis catalysts: Supported homogeneous catalysis vs. surface organometallic chemistry [J].

Coperet, C. ;

Basset, J. -M. .

ADVANCED SYNTHESIS & CATALYSIS, 2007, 349 (1-2) :78-92

[9] Practical New Strategies for Immobilising Ruthenium Alkylidene Complexes: Part I IMMOBILISATION VIA PHOSPHANE, ALKYLIDENE AND N-HETEROCYCLIC CARBENE LIGANDS [J].

Dragutan, Ileana ;

Dragutan, Valerian .

PLATINUM METALS REVIEW, 2008, 52 (02) :71-82

[10] Hybrid silica materials derived from Hoveyda-Grubbs ruthenium carbenes. Electronic effects of the nitro group on the activity and recyclability as diene and enyne metathesis catalysts [J].

Elias, Xavier ;

Pleixats, Roser ;

Man, Michel Wong Chi .

TETRAHEDRON, 2008, 64 (28) :6770-6781

← 1 2 3 4 →