Electrochemically driven reductive cyclization of o-nitroanilines: synthesis of 1,2-fused benzimidazoles and benzo[d]imidazoles.

Abstract

The electrochemical synthesis of 1,2-fused benzimidazoles and benzo[d]imidazoles from o-nitroanilines in an undivided cell under constant current conditions was developed. The electrosynthesis proceeded through a tandem process involving nitro reduction/C(sp³)-H amination/condensation. The method can accommodate a broad range of o-nitroanilines and results in the desired products in yields of up to 99%. A plausible reaction mechanism was proposed on the basis of controlled experiments and cyclic voltammetry (CV) analysis. The benefits of the developed method include one-pot synthesis, open-air conditions, gram-scale synthesis and no requirement for a strong reductant.