Selenium-Electrocatalytic Cyclization of 2-Vinylanilides towards Indoles of Peptide Labeling

Abstract

A novel selenium-electrocatalytic intramolecular cyclization of 2-vinylanilides for synthesis of functionalized indoles and azaindoles has been developed. In contrast to the previous synthetic methods, this sustainable protocol enabled unparalleled broad substrates scope for viable indoles with highly functional and sensitive groups by employing recyclable selenium catalyst, under mild, metal- and external-oxidant-free conditions. The approach can be used to the late-stage modification of complex bioactive molecular system, thereby setting the stage for versatile syntheses of decorated indoles with peptide labeling. A plausible catalytic pathway was proposed.

Keywords: electrochemistry; indoles; intramolecular cyclization; peptide labeling; selenium catalyst.