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



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.

Version notes

One of our recent relevant work was cited and discussed to support the conclusion of this work, see ref 13.


Supplementary material

supporting information
General information, experimental procedures, new com-pound characterization, crystallographic data, spectroscopic data, and NMR spectra.