Sulfur Assisted Tandem Electrophilic Fluorinative Deacylation: Synthesis of α-Fluoro β-Ketosulfides

A successful synthesis of alpha-fluoro-beta-ketosulfides using an electrophilic fluorination method has been reported for the first time. The reaction proceeds via an electrophilic fluorination of alpha-sulfenyl-beta-diketones followed by an unexpected tandem deacylation. The resulting products, alpha-fluoro-beta-ketosulfides, are easily oxidized to the corresponding alpha-fluoro-beta-ketosulfones, which can be used for further useful olefination reactions.