Green electrochemical strategy for one-step synthesis of new catechol derivatives

Abstract

In this paper, we present promising results in the green electrochemical oxidation of catechol in the presence of three different thiol nucleophiles at the surface of a glassy carbon electrode in an aqueous solution using cyclic voltammetry (CV). The outcome indicated the synthesis of some new heterocyclic compounds functionalized with phenolic, triazole, triazine and pyrimidine groups. The effects of repetitive cycling, nucleophile concentrations and sweep rates were explored to get more information about the systems. The voltammetric data showed that the electro-generated o-benzoquinone is a quite reactive intermediate, which in aqueous solutions can quickly participate in a Michael-addition reaction with any one of the nucleophiles to form the corresponding products. The structures of all newly electro-synthesized compounds were confirmed by elemental analyses and FT-IR, 1H NMR, 13C-NMR and MS spectra. The one-pot synthesis strategy led to new organics with high purities and good yields under green conditions without harmful reagents.