Influence of Adsorption Geometry in the Heterogeneous Enantioselective Catalytic Hydrogenation of a Prototypical Enone

Beaumont, Simon K.; Kyriakou, Georgios; Watson, David J.; Vaughan, Owain P.H.; Papageorgiou, Anthoula C.; Lambert, Richard M.

doi:10.1021/jp105960w

Influence of Adsorption Geometry in the Heterogeneous Enantioselective Catalytic Hydrogenation of a Prototypical Enone

Beaumont, Simon K.; Kyriakou, Georgios; Watson, David J.; Vaughan, Owain P.H.; Papageorgiou, Anthoula C.; Lambert, Richard M.

Authors

Dr Simon Beaumont simon.beaumont@durham.ac.uk
Associate Professor

Georgios Kyriakou

David J. Watson

Owain P.H. Vaughan

Anthoula C. Papageorgiou

Richard M. Lambert

Abstract

Asymmetric catalysis is of paramount importance in organic synthesis and, in current practice, is achieved by means of homogeneous catalysts. The ability to catalyze such reactions heterogeneously would have a major impact both in the research laboratory and in the production of fine chemicals and pharmaceuticals, yet heterogeneous asymmetric hydrogenation of C═C bonds remains hardly explored. Very recently, we demonstrated how chiral ligands that anchor robustly to the surface of Pd nanoparticles promote asymmetric catalytic hydrogenation: ligand rigidity and stereochemistry emerged as key factors. Here, we address a complementary question: how does the enone reactant adsorb on the metal surface, and what implications does this have for the enantiodifferentiating interaction with the surface-tethered chiral modifiers? A reaction model is proposed, which correctly predicts the identity of the enantiomer experimentally observed in excess.

Citation

Beaumont, S. K., Kyriakou, G., Watson, D. J., Vaughan, O. P., Papageorgiou, A. C., & Lambert, R. M. (2010). Influence of Adsorption Geometry in the Heterogeneous Enantioselective Catalytic Hydrogenation of a Prototypical Enone. Journal of Physical Chemistry C, 114(35), 15075-15077. https://doi.org/10.1021/jp105960w

Journal Article Type	Article
Publication Date	Aug 18, 2010
Deposit Date	Mar 8, 2014
Publicly Available Date	Apr 15, 2014
Journal	Journal of Physical Chemistry C
Print ISSN	1932-7447
Publisher	American Chemical Society
Peer Reviewed	Peer Reviewed
Volume	114
Issue	35
Pages	15075-15077
DOI	https://doi.org/10.1021/jp105960w

Files

Accepted Journal Article (223 Kb)
PDF

Copyright Statement
This document is the Accepted Manuscript version of a Published Work that appeared in final form in The Journal of Physical Chemistry C, copyright © American Chemical Society after peer review and technical editing by the publisher. To access the final edited and published work see http://pubs.acs.org/doi/abs/10.1021/jp105960w.