Paired Electrosynthesis of Diacid and Diol Precursors Using Dienes and CO2 as the Carbon Source

A new electrochemical methodology was devised and optimized, allowing a net incorporation of carbon dioxide in conjugated dienes in a one-compartment cell using a non-sacrificial anode. This divergent paired electrosynthesis of diacid and diol precursors was achieved through simultaneous cathodic carboxylation and anodic acetoxylation of conjugated dienes. After optimization of the reaction conditions, 1,3-cyclohexadiene was converted to its corresponding 1,4-dicarboxylate salt and 1,4-diacetate ester with high yields and current efficiencies. A large effect of alkyl substitution and molecular configuration on the reactivity of conjugated double bonds towards carboxylation and acetoxylation was observed.