Transfer Hydrogenation of Ketones and Activated Olefins Using Chelating NHC Ruthenium Complexes

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Title: Transfer Hydrogenation of Ketones and Activated Olefins Using Chelating NHC Ruthenium Complexes
Authors: Horn, Sabine
Gandolfi, Claudio
Albrecht, Martin
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Date: Jun-2011
Abstract: 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.
Funding Details: European Research Council
Type of material: Journal Article
Publisher: Wiley
Journal: European Journal of Inorganic Chemistry
Volume: 2011
Issue: 18
Start page: 2863
End page: 2868
Copyright (published version): 2011 Wiley
Keywords: RutheniumN-Heterocyclic carbeneHydrogenationTransfer hydrogenationKetonesChemoselectivityAsymmetric transfer hydrogenationEnantioselective transfer hydrogenationHighly efficient catalystsCarbonyl-compoundsCarbene complexesAllylic alcoholsBase hydrolysisMechanistic aspectsIridium complexesPolar bonds
DOI: 10.1002/ejic.201100143
Language: en
Status of Item: Peer reviewed
Appears in Collections:Chemistry Research Collection

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