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

15 February 2022, Version 2
This content is a preprint and has not undergone peer review at the time of posting.


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.


[2 3]-sulfonyloxy migration
vinyl sulfonate
hypervalent iodine
late-stage modification

Supplementary materials

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


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