Chirality Transfer in Imidazolium Camphorsulfonate Ionic Liquids through Ion Pairing Effects

Journal article


Publication Details

Author(s): Schneiders K, Bösmann A, Schulz P, Wasserscheid P
Journal: Advanced Synthesis & Catalysis
Publisher: Wiley-VCH Verlag
Publication year: 2009
Volume: 351
Journal issue: 3
Pages range: 432--440
ISSN: 1615-4150


Abstract


The paper describes our studies on ion pair interactions in ionic liquids (IL) using an asymmetric hydrogenation reaction as probe. Three different ionic liquids carrying prochiral keto-functionalized cations were hydrogenated in the presence of their chiral, enantiomerically pure counter-ion using an achiral heterogeneous ruthenium catalyst. For the hydrogenation of N-(3$\prime$-oxobutyl)-N-methylimidazolium camphorsulfonate (2), N-(3$\prime$-oxobutyl)imidazolium camphorsulfonate (4) and N-(5$\prime$-oxohexyl)-N-methylimidazolium camphorsulfonate (6) we found a strong dependency of the enantiomeric excess (ee in the cation) on the polarity of the solvent, the concentration of the IL and the structure of the IL. The highest ee values of up to 94{\%} were found for the hydrogenation of 2 in ethanol. Interestingly, we observed that the ee (and consequently the strength of ion pair interaction) had a pronounced maximum for a certain concentration of the IL in the solvent depending on the nature of the solvent and on the substrate. Remarkably, the concentration leading to the maximum ee could be rationalized by independent determination of the degree of dissociation which was obtained by a combination of diffusion-ordered NMR spectroscopy and conductivity measurements.



FAU Authors / FAU Editors

Bösmann, Andreas Dr.
Lehrstuhl für Chemische Reaktionstechnik
Schneiders, Karola
Lehrstuhl für Chemische Reaktionstechnik
Schulz, Peter Dr.
Lehrstuhl für Chemische Reaktionstechnik
Wasserscheid, Peter Prof. Dr.
Lehrstuhl für Chemische Reaktionstechnik


Additional Organisation
Exzellenz-Cluster Engineering of Advanced Materials


Research Fields

D Catalytic Materials
Exzellenz-Cluster Engineering of Advanced Materials


How to cite

APA:
Schneiders, K., Bösmann, A., Schulz, P., & Wasserscheid, P. (2009). Chirality Transfer in Imidazolium Camphorsulfonate Ionic Liquids through Ion Pairing Effects. Advanced Synthesis & Catalysis, 351(3), 432--440. https://dx.doi.org/10.1002/adsc.200800569

MLA:
Schneiders, Karola, et al. "Chirality Transfer in Imidazolium Camphorsulfonate Ionic Liquids through Ion Pairing Effects." Advanced Synthesis & Catalysis 351.3 (2009): 432--440.

BibTeX: 

Last updated on 2018-06-08 at 15:23