Benzothiazolium salts as reagents for the deoxygenative perfluoroalkylthiolation of alcohols

A series of 2-(perfluoroalkylthio)benzothiazolium (BT-SRF) salts have been synthesized that serve as convenient sources of hitherto underexplored perfluoroalkylthiolate anions. An investigation of their reactivity in a deoxygenative nucleophilic substitution reaction led to the development of an unprecedented process that provides pentafluoroethyl and heptafluoropropyl thioethers directly from readily available alcohols.

Automated summary

A series of BT-SRF salts have been synthesized for the first time, providing a convenient source of perfluoroalkylthiolate anions. These salts were found to react in a deoxygenative nucleophilic substitution reaction, leading to the direct synthesis of pentafluoroethyl and heptafluoropropyl thioethers from readily available alcohols.