Benzothiazolium salts as reagents for the deoxygenative perfluoroalkylthiolation of alcohols

Beilstein J Org Chem. 2021 Jan 8:17:83-88. doi: 10.3762/bjoc.17.8. eCollection 2021.

Abstract

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.

Keywords: alcohols; benzothiazolium salts; deoxygenative reactions; fluorine; perfluoroalkylthiolation; thioethers.

Grants and funding

Funded by the Daimler und Benz Stiftung (Postdoctoral Scholarship, Project No.: 32-04/18) and the Deutsche Forschungsgemeinschaft (DFG, German Research Foundation) – Project-ID 387284271 – SFB 1349 (gefördert durch die Deutsche Forschungsgemeinschaft (DFG) – Projektnummer 387284271 – SFB 1349)). Financial support from the Fonds der Chemischen Industrie (Sachkostenzuschuss) is also gratefully acknowledged.