Electro-oxidative Trimerization of 1,2-Dimethoxybenzene: Reductive Workup Strategy and Alternating Current Electrolysis to Peel off the Precipitated Radical Cation Ion Pair

An oxidative trimerization of catechol and its derivatives affords triphenylene derivatives. Under these electrochemical conditions, overoxidation results in precipitation of a radical cation pair of triphenylenes with a counter anion, which prevents efficient synthesis. A reductive workup strategy, in which the precipitate is peeled from the electrodes, affords the trimer in good yield. Furthermore, alternating current (AC) electrolysis provides a convenient synthesis without any precipitation.

Automated summary

An oxidative trimerization of catechol and its derivatives leads to the formation of triphenylene derivatives. However, the precipitation of a radical cation pair during overoxidation hinders efficient synthesis. A reductive workup strategy and alternating current (AC) electrolysis offer effective solutions.