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

Reaction Kinetics, Mechanisms and Catalysis - Tập 126 - Trang 439-451 - 2018
Réka Gombos1, Brigitta Nagyházi1, Ferenc Joó1,2
1Department of Physical Chemistry, University of Debrecen, Debrecen, Hungary
2MTA-DE Redox and Homogeneous Catalytic Reaction Mechanisms Research Group, Debrecen, Hungary

Tóm tắt

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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