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Hydrogenation of α,β-unsaturated aldehydes in aqueous media with a water-soluble Pd(II)-sulfosalan complex catalyst

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Abstract

A water-soluble Pd(II)-salan complex Na2[Pd(HSS)] (HSS = sulfonated tetrahydrosalen or sulfosalan) was examined as a hydrolytically stable catalyst for hydrogenation of various aldehydes. Na2[Pd(HSS)] was found to be a highly selective catalyst towards hydrogenation of C=C over C=O bonds in cinnamaldehyde and crotonaldehyde (used as representative α,β-unsaturated aldehydes). Kinetic measurements revealed an important role of protonation/deprotonation of one of the phenolate oxygens of the N2O2 coordination framework in the reaction mechanism. Na2[Pd(HSS)] was also found an efficient catalyst for transfer hydrogenation of aldehydes from isopropanol in the presence of various bases. The results show, for the first time, the usefulness of easily accessible, hydrolytically stable Pd(II)-salan type catalysts in aqueous catalytic organometallic hydrogenations.

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Acknowledgements

The research was supported by the EU and co-financed by the European Regional Development Fund under the Projects GINOP-2.3.2-15-2016-00008 and GINOP-2.3.3-15-2016-00004.

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Authors and Affiliations

  1. Department of Physical Chemistry, University of Debrecen, P.O. Box 400, Debrecen, 4002, Hungary

    Réka Gombos, Brigitta Nagyházi & Ferenc Joó

  2. MTA-DE Redox and Homogeneous Catalytic Reaction Mechanisms Research Group, P.O. Box 400, Debrecen, 4002, Hungary

    Ferenc Joó

Authors
  1. Réka Gombos
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  2. Brigitta Nagyházi
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  3. Ferenc Joó
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Correspondence to Ferenc Joó.

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Gombos, R., Nagyházi, B. & Joó, F. Hydrogenation of α,β-unsaturated aldehydes in aqueous media with a water-soluble Pd(II)-sulfosalan complex catalyst. Reac Kinet Mech Cat 126, 439–451 (2019). https://doi.org/10.1007/s11144-018-1488-8

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  • DOI: https://doi.org/10.1007/s11144-018-1488-8

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