Transfer hydrogenation of ketones and activated olefins using chelating NHC ruthenium complexes

Horn, Sabine; Gandolfi, Claudio; Albrecht, Martin

doi:10.1002/ejic.201100143

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Transfer hydrogenation of ketones and activated olefins using chelating NHC ruthenium complexes

Horn, Sabine School of Chemistry & Chemical Biology, University College Dublin,Ireland
Gandolfi, Claudio Department of Chemistry, University of Fribourg, Switzerland
Albrecht, Martin School of Chemistry & Chemical Biology, University College Dublin,Ireland - Department of Chemistry, University of Fribourg, Switzerland

04.05.2011

Published in:

European Journal of Inorganic Chemistry. - 2011, vol. 2011, no. 18, p. 2863–2868

English N-Heterocyclic carbene (NHC) ruthenium complexes consisting of different donor substituents attached to the NHC ligand efficiently catalyse the transfer hydrogenation of ketones and of activated olefins in α,β-unsaturated ketones to give saturated alcohols. The most active catalyst precursor contains a tethered olefin as a hemilabile donor site. This complex also converts nitriles and, depending on the reaction conditions, either benzylamines are produced by means of transfer hydrogenation, or amides from formal addition of H₂O. Kinetic analysis of the double hydrogenation of α,β-unsaturated ketones indicates fast isomerisation of the enol intermediate to its saturated ketone tautomer prior to the second hydrogenation.

Faculty

Faculté des sciences et de médecine

Department

Département de Chimie

Language