Mono and difluorination of centers α to sulfonates and phosphonates using AcOF

Acetyl hypofluorite, made easily from diluted fluorine and AcONa is very efficient in fluorinating anionic centers. Compounds containing the moieties CH2SO2 or COCH2PO react with bases to create the corresponding anions which can react with AcOF to produce derivatives containing either the CHFSO2 or COCHFPO groups. Larger excess of base and AcOF result in the difluoro compounds containing the CF2SO2 or COCF2PO sub-structures. The fluorinations proceed fast and smoothly and usually with very good yield even when the base is dissolved in aqueous solution as is the case with K2CO3 or NaHCO3.

Graphical abstractAcetyl hypofluorite is very efficient in fluorinating anionic centers. Anions of compounds containing the moieties CH2SO2 or COCH2PO react with AcOF to produce derivatives containing the CHFSO2 or COCHFPO groups.Figure optionsDownload full-size imageDownload as PowerPoint slideHighlights► This paper highlights the usefulness and versatility of acetyl hypofluorite, made directly from fluorine ► It is a power nucleophile and is able to fluorinate even hydrated anions which were created with K2CO3 or NaHCO3 ► The yields are very good and the reaction fast so they are also very suitable for PET uses providing electrophilic fluorination is required.