Palladium-Catalyzed Carboxylation of Vinyl Triflates. Electrosynthesis of α,β-Unsaturated Carboxylic Acids

Anny Jutand; Serge Négri

doi:10.1055/s-1997-3241

Synlett 1997; 1997(6): 719-721
DOI: 10.1055/s-1997-3241

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Palladium-Catalyzed Carboxylation of Vinyl Triflates. Electrosynthesis of α,β-Unsaturated Carboxylic Acids

Anny Jutand^* , Serge Négri

^*Ecole Normale Supérieure, Département de Chimie, URA CNRS 1679, 24 Rue Lhomond, 75231 Paris Cedex 5, France, Fax: 33 1 44 32 33 25; E-mail: jutand@chimene.ens.fr

Abstract

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The electrocarboxylation of vinyl triflates performed with carbon dioxide and a catalytic amount of PdCl₂(PPh₃)₂ affords α,β-unsaturated carboxylic acids. The reacitivity of vinyl triflates has been reversed in the presence of an electron source, since they now react with electrophiles. The reaction proceeds by an activation of the C-O bond of the vinyl triflate by a palladium(0) complex followed by an activation by electron transfer, of the vinylpalladium(II) complex formed in the oxidative addition.

vinyl triflates - CO₂ - palladium - electron transfer

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