Rh-Catalyzed C–H bond alkylation of indoles with α,α-difluorovinyl tosylate via indolyl group migration

Abstract

Herein we demonstrate that an alkylation of indoles could be accessed through C–H bond functionalization with α,α-difluorovinyl tosylate. The key aspect for the effective alkylation is the influence of the fluorine substituents on the reactivity of the CC double bond, allowing regioselective insertion as well as an indolyl group shift process. Furthermore, the fluorides are removed through alcoholysis to furnish the alkylation product as a traceless auxiliary.