Journal
EUROPEAN JOURNAL OF INORGANIC CHEMISTRY
Volume -, Issue 18, Pages 2863-2868Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejic.201100143
Keywords
Ruthenium; N-Heterocyclic carbene; Hydrogenation; Transfer hydrogenation; Ketones; Chemoselectivity
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Funding
- Swiss National Science Foundation
- European Research Council [ERC StG 208561]
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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 alpha,beta-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 alpha,beta-unsaturated ketones indicates fast isomerisation of the enol intermediate to its saturated ketone tautomer prior to the second hydrogenation.
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