Recent advances in electrocatalytic generation of indole-derived radical cations and their applications in organic synthesis

Abstract

Indole-derived radical cations, open-shell reactive species, display distinctive dual reactivity due to the carbon-centered radical and more electrophilic carbocation, which frequently appear in a variety of single electron oxidation reactions for synthesizing structurally diverse functionalized indoles and indolines. Electrocatalysis is considered as a synthetically attractive and environmentally friendly alternative for driving the single electron oxidation of indoles. Remarkable achievements in electrocatalytic indole-derived radical cation-mediated indole functionalization have been realized so far. This review comprehensively summarizes the recent progresses in the applications of electrocatalytic indole radical cations, including C(sp2)–H functionalization, dearomative 2,3-difunctionalization, and ring-opening reaction, emphasizing the vital single electron oxidation steps of indoles, the substrates scope and limitations, and the reaction mechanisms.