Electrochemical Oxidation of Catechols in the Presence of Pyrimidine-2-thiol: Application to Electrosynthesis

The electrooxidation of catechols (1a–d) in the presence of pyrimidine-2-thiol (3) as a nucleophile in aqueous solution is described. The mechanistic investigations using cyclic voltammetry and controlled potential coulometry indicate that the quinone derived from catechols participates in a Michael addition reaction with pyrimidine-2-thiol to form corresponding catechol derivatives of 6a–d (ECEC). The efficient electrosynthesis of 6a–d has been performed at carbon rod electrodes in an undivided cell in good yield and purity.