Pentafluorosulfanoxylation of Hypervalent Chlorines and Bromines for Access to Pentafluoro(biaryloxy)-λ6-sulfanes

The SF₅O group has been less explored as a highly fluorinated substituent on an organic framework. In fact, only a few SF₅O-containing compounds have been reported, and the preparation of SF₅O-containing compounds relied on hazardous reagents and special apparatuses. Herein we describe safe and efficient access to various pentafluoro(aryloxy)-λ⁶-sulfanes (ArOSF₅) through the reaction of hypervalent λ³-chlor(brom)anes with [Et₃MeN]⁺[OSF₅]^-. The synthetic and application potentials of ArOSF₅ moieties were demonstrated by the inertness of OSF₅ moieties in the presence of palladium catalysts, alkalis, and nucleophiles.