Electrochemical Synthesis of Aminoquinones through Oxidative Coupling of 4-tert-Butylcatechol and Benzenamines

The electrochemical oxidation of 4-tert-butylcatechol in the presence of a series of benzenamines has been evaluated in aqueous solution by means of cyclic voltammetry and controlled-potential coulometry. Results indicate that 4-tert-butylcatechol undergoes a two-electron oxidation at the surface of electrode to 4-tert-butylquinone followed by Michael addition reaction with benzenamine. This study has established the formation of aminoquinones as final products via the ECE mechanism. This procedure would be a good candidate for synthesis of aminoquinones in one-pot process, green conditions and good purity.