Enhanced enantioselectivity of chiral hydrogenation catalysts after immobilisation in thin films of ionic liquid

Kam Loon Fow; Stephan Jaenicke; Thomas E. Müller; Carsten Sievers

doi:10.1016/j.molcata.2006.11.050

Enhanced enantioselectivity of chiral hydrogenation catalysts after immobilisation in thin films of ionic liquid

Kam Loon Fow, Stephan Jaenicke, Thomas E. Müller, Carsten Sievers

Research output: Journal Publication › Article › peer-review

32 Citations (Scopus)

Abstract

Chiral organometallic complexes were immobilized in silica supported thin films of ionic liquid. The heterogenized catalysts were tested in the hydrogenation of acetophenone, which was chosen as test reaction for the enantioselective reduction of prochiral ketones. High enantioselectivities (up to 74% ee) were achieved in supported ionic liquids using a catalyst/substrate pair, which showed no enantioselectivity in methanol. This is attributed to the unique solvent properties of ionic liquids including the formation of solvent cages of ionic liquid molecules around the complexes. Within these cages, transition states are modified and chemical transformations follow alternative reaction pathways.

Original language	English
Pages (from-to)	239-247
Number of pages	9
Journal	Journal of Molecular Catalysis A: Chemical
Volume	279
Issue number	2
DOIs	https://doi.org/10.1016/j.molcata.2006.11.050
Publication status	Published - 18 Jan 2008
Externally published	Yes

Keywords

Enantioselectivity
Hydrogenation
Immobilisation
Ionic liquid
Ketone
Two-phase catalysis

ASJC Scopus subject areas

Catalysis
Process Chemistry and Technology
Physical and Theoretical Chemistry

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10.1016/j.molcata.2006.11.050

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title = "Enhanced enantioselectivity of chiral hydrogenation catalysts after immobilisation in thin films of ionic liquid",

abstract = "Chiral organometallic complexes were immobilized in silica supported thin films of ionic liquid. The heterogenized catalysts were tested in the hydrogenation of acetophenone, which was chosen as test reaction for the enantioselective reduction of prochiral ketones. High enantioselectivities (up to 74% ee) were achieved in supported ionic liquids using a catalyst/substrate pair, which showed no enantioselectivity in methanol. This is attributed to the unique solvent properties of ionic liquids including the formation of solvent cages of ionic liquid molecules around the complexes. Within these cages, transition states are modified and chemical transformations follow alternative reaction pathways.",

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AU - Fow, Kam Loon

AU - Jaenicke, Stephan

AU - Müller, Thomas E.

AU - Sievers, Carsten

PY - 2008/1/18

Y1 - 2008/1/18

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AB - Chiral organometallic complexes were immobilized in silica supported thin films of ionic liquid. The heterogenized catalysts were tested in the hydrogenation of acetophenone, which was chosen as test reaction for the enantioselective reduction of prochiral ketones. High enantioselectivities (up to 74% ee) were achieved in supported ionic liquids using a catalyst/substrate pair, which showed no enantioselectivity in methanol. This is attributed to the unique solvent properties of ionic liquids including the formation of solvent cages of ionic liquid molecules around the complexes. Within these cages, transition states are modified and chemical transformations follow alternative reaction pathways.

KW - Enantioselectivity

KW - Hydrogenation

KW - Immobilisation

KW - Ionic liquid

KW - Ketone

KW - Two-phase catalysis

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Enhanced enantioselectivity of chiral hydrogenation catalysts after immobilisation in thin films of ionic liquid

Abstract

Keywords

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