One-step Oxidative Monofluorination of Electron-Deficient Sulfoxides to Access Highly Lewis Acidic Sulfur(VI) Cations
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Updated: Aug 30, 2025

Synthesis of a Thiol Building Block for the Crystallization of a Semiconducting Gyroidal Metal-sulfur Framework
Published on: April 9, 2018
Jordan Berreur1, Alberto Diez-Varga1, Augustin Manel1
1Université de Strasbourg, Université de Haute-Alsace, CNRS, LIMA, UMR 7042, 67000, Strasbourg, France.
Abstract:
The strongly oxidizing, powerful electrophilic fluorination reagent [FXe][OTf] is shown to effect direct oxidative monofluorination of sulfoxides. This one-step, chloride promoter-free methodology provides access to so far inaccessible, yet highly desirable strongly Lewis acidic fluorosulfoxonium cations from electron-deficient and/or sterically demanding sulfoxides that are shown to be practically unreactive towards the previously reported XeF2 /NEt4 Cl system. Experimental and density functional theory studies have been conducted to assess the Lewis acidities of the prepared sulfur(VI) cations. Preliminary results obtained with chiral sulfoxides provide early insights into the mechanism of these fluorination reactions.
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