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

Horn, Sabine ; Gandolfi, Claudio ; Albrecht, Martin

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

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,... More

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    Title
    • Transfer hydrogenation of ketones and activated olefins using chelating NHC ruthenium complexes
    Author
    • 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
    Document Type
    • Postprint
    Publication Date
    • 2011-05-04
    OAI-PMH Identifier
    • oai:doc.rero.ch:20110930151704-EJ
    Submission No.
    • 20110930151704-EJ
    Summary
    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.