Synthesis of -Tosyloxylated gem-Difluoroalkanes via Oxidative Fluorination of Vinyl Sulfonates Featuring A [2,3]-Sulfonyloxy Migration

Abstract

The gem-difluoroalkanes widely exist in pharmaceuticals, agrochemicals and materials. Reported herein is a facile synthesis of tosyloxylated gem-difluoroalkanes via an oxidative fluorination of readily available vinyl sulfonates. An intriguing [2,3]-sulfonyloxy migration is involved as a key step. The OTs group in the product enables a divergent and modular synthesis of a wide variety of functionalized gem-difluoroalkanes via reliable SN2 reactions. Notable features of this protocol include mild reaction conditions, high efficiency and remarkably good functional-group tolerance.