Halofluorination of alkenes mediated by 1,1,3,3,3-pentafluoropropene-diethylamine adduct

1,1,3,3,3-Pentafluoropropene-diethylamine complex (PFPDEA) has been found useful as a fluoride source in halofluorination reactions of various olefins. Reactions proceeded with PFPDEA and N-halosuccinimide (NXS, X = Br, I) or 1,3-dibromo-5,5-dimethylhydantoin (DBH), as sources of electrophilic halogens, in a regioselective manner.

1,1,3,3,3-Pentafluoropropene-diethylamine complex (PFPDEA) has been found useful as a fluoride source in halofluorination reactions of various olefins. Reactions proceeded with PFPDEA and N-halosuccinimide (NXS, X = Br, I) or 1,3-dibromo-5,5-dimethylhydantoin (DBH), as sources of electrophilic halogens, in a regioselective manner.Figure optionsDownload as PowerPoint slideHighlights
► Pentafluoropropene-diethylamine adduct is an efficient reagent in halofluorination as a source of nucleophilic fluoride.
► The halofluorination is highly regioselectivite (formation of Markovnikov products).
► The halofluorination is stereospecific in an anti-sence.
► The method allows introduction of fluorine into alkenes under mild conditions.