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

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.

Automated summary

A novel selenium-electrocatalytic intramolecular cyclization has been developed for the synthesis of functionalized indoles and azaindoles. This sustainable method enables broad substrate scope and synthesis of highly functional indoles under mild conditions, using a recyclable selenium catalyst.