Immobilization of Rhodium Diphosphine Complexes on Mesoporous Al-MCM-41 Materials: Catalysts for Enantioselective Hydrogenation

Heterogeneous chiral catalysts for the enantioselective hydrogenation of prochiral alkenes are prepared from chiral rhodium diphosphine complexes and Al-MCM-41. Impregnation of the mesoporous carrier Al-MCM-41 with the organometallic complexes in dichloromethane leads to strong and not leaching hydr...

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Bibliographic Details
Published inJournal of catalysis Vol. 203; no. 1; pp. 150 - 156
Main Authors Wagner, H.H., Hausmann, H., Hölderich, W.F.
Format Journal Article
LanguageEnglish
Published Amsterdam Elsevier Inc 01.10.2001
Elsevier
Subjects
asymmetric
Catalysis
Catalysts: preparations and properties
Chemistry
Exact sciences and technology
General and physical chemistry
hydrogenation
immobilization
MCM-41
phosphine
rhodium
Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry
phosphine
immobilization
MCM-41
asymmetric
hydrogenation
rhodium
Enantioselectivity
Molecular structure
Phosphine
Organic ligand
Immobilization
Chiral compound
Transition metal Complexes
Hydrogenation
Porous material
Supported catalyst
Mesoporosity
Heterogeneous catalysis
Ester
Rhodium Complexes
Platinoid Complexes
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Summary:Heterogeneous chiral catalysts for the enantioselective hydrogenation of prochiral alkenes are prepared from chiral rhodium diphosphine complexes and Al-MCM-41. Impregnation of the mesoporous carrier Al-MCM-41 with the organometallic complexes in dichloromethane leads to strong and not leaching hydrogenation catalysts. The catalysts are characterized by spectroscopic methods such as FT-IR and MAS-NMR as well as thermoprogrammed desorption of ammonia, thermogravimetric analysis, and nitrogen sorption experiments. The hydrogenation of dimethylitaconate was studied as a test reaction. The immobilized catalysts showed high activity and excellent regio- and enantioselectivity. Up to 92% ee, 100% conversion, and 99% regioselectivity were observed for the hydrogenation of dimethyl (R)-methylsuccinate. The catalysts could be reused without any regeneration procedure and with no loss of catalytic acitivity. Leaching of the homogeneous complex out of the MCM-41 framework was not observed.
ISSN:0021-9517
1090-2694
DOI:10.1006/jcat.2001.3296