Facile synthesis of aryl-substituted 2-alkenoic acids by electroreductive carboxylation of vinylic bromides using a magnesium anode

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Electrochemical carboxylation of phenyl-substituted vinylic bromides in the presence of atmospheric carbon dioxide using a platinum cathode and a magnesium anode gave the corresponding α,β-unsaturated carboxylic acids in 63–92% isolated yields. A precursor of ibuprofen, 2-( p-isobutylphenyl) propenoic acid, was readily obtained in a 93% yield by a similar electrochemical carboxylation of 1-bromo-1-( p-isobutylphenyl)ethene. Stereochemical studies showed that thermodynamically less stable Z-isomers were preferentially produced from either E- or Z-vinylic bromides in these electrochemical carboxylations.