Catalytic properties of the Pd/C – triethylamine system

In the presence of Pd/C and a catalytic amount of triethylamine, allylic alcohols are isomerized into the corresponding carbonyl compounds.The isomerization is accompanied by Pd/Ccatalyzed redox processes to give the saturated alcohol and the corresponding α,β-unsaturated ketone.Pd/C also catalyses the conjugate reduction of activated double bonds, using triethylamine as the source of the two newly incorporated hydrogen atoms, probably via a hydrido complex.During the reaction, the triethylamine undergoes unexpected Pd/C-catalyzed oligomerization to produce elongated aliphatic tertiary amines and ethylamine, which, in the conjugate reduction of α,β-unsaturated esters, resulted in the formation of the reduced ethylamides following a domino transamidation.