Synthesis of Polyfluoroalkyl Aryl Ethers Mediated by Sulfuryl Fluoride as a Traceless Activator
Résumé
Herein we report the metal-free synthesis of polyfluoroalkyl aryl ethers via nucleophilic substitution of fluorosulfonates, obtained in one pot by bubbling of sulfuryl fluoride (SO2F2). Polyfluoroalkyl aryl ethers are present in a variety of biologi-cally active compounds, but previous methods to access them required metal catalysts or harsh conditions. With this meth-od, their synthesis is possible under mild conditions and with a short reaction time (30 minutes), from commercially availa-ble starting materials and in yields up to 97%. Various fluorinated alcohols could be used as electrophiles, and a diversity of electron withdrawing groups on the aryl or heteroaryl group were tolerated.
