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Catalytic Properties of the Pd/C - Triethylamine System

Yoann Coquerel 1, * Jean Rodriguez 1, * 
* Corresponding author
1 STeRéO
ISM2 - Institut des Sciences Moléculaires de Marseille
Abstract : 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/C-catalyzed 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.
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Submitted on : Tuesday, March 20, 2012 - 3:50:48 PM
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  • HAL Id : hal-00681023, version 1



Yoann Coquerel, Jean Rodriguez. Catalytic Properties of the Pd/C - Triethylamine System. ARKIVOC - Online Journal of Organic Chemistry, Arkat USA Inc, 2008, XI, pp.227-237. ⟨hal-00681023⟩



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