Electrochemical oxidation of catechols in the presence of ketene N,O-acetals: indole formation versus α-arylation

Anodic oxidation of catechols has been investigated in the presence of ketene N,O-acetals using cyclic voltammetry and constant current electrolysis methods. The results show that in the presence of ketene N,O-acetals, the anodic oxidation of 4-methylcatechol affords α-arylated products in satisfactory yields. Meanwhile, indoles can be synthesized from simple 3-substituted catechols or catechol itself following an ECEC mechanism. In addition, either α-arylation or indole formation could be the dominant pathway by simply modifying the composition of the electrolyte solution.