Thianthrenation-enabled metal-free heterodifunctionalization of unactivated alkenes with thiols and readily available N/O nucleophiles

Abstract

The 1,2-heterodifunctionalization of alkenes represents a powerful strategy for constructing valuable molecules. However, simple, green, and general methods for these transformations are still highly desirable. Herein, we report a thianthrenation-enabled three-component reaction of the alkenyl thianthrenium salts with thiols and common nucleophiles including amines, carboxylic acids, and water for the 1,2-sulfenylamination, 1,2-acyloxysulfenylation and 1,2-hydroxysulfenylation of alkenes. This strategy establishes a versatile platform for the heterodifunctionalization of alkenes, featuring broad substrate scope, simple reaction conditions and the absence of transition metals.