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Synthesis of Polyfluoroalkyl Aryl Ethers Mediated by Sulfuryl Fluoride as a Traceless Activator
Clotilde Plaçais1, Lilian Wisson1, Isabelle Chataigner2,3
1Université de Strasbourg, Université de Haute-Alsace, CNRS, UMR 7042-LIMA, ECPM, 25 Rue Becquerel, Strasbourg 67087, France.
Abstract:
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 biologically active compounds, but previous methods for accessing them required metal catalysts or harsh conditions. With this method, their synthesis is possible under mild conditions and with a short reaction time (30 min) from commercially available starting materials and in yields of ≤97%. Various fluorinated alcohols could be used as electrophiles, and a diversity of electron-withdrawing groups on the aryl or heteroaryl group were tolerated.
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