PhI(OCOCF3)2-mediated metal-free 2,3-difunctionalization of indoles: direct access to carbochalcogenated scaffolds

Abstract

We report a metal-free approach for the oxidative difunctionalization of indole moieties using a hypervalent iodine reagent. This protocol facilitates a metal-free, environmentally friendly, and efficient oxidative C(sp²)–H coupling reaction that utilises indole, naphthoquinones, and diphenyl dichalcogenides. The method has been designed so that it should run under mild conditions to enable the formation of C(sp²)–C and C(sp²)–S/Se bonds with good yields and a wide range of relevant substrates. Additionally, our approach offers a valuable pathway for the modification of drug molecules, which further enhances its utility in organic synthesis.