The
regioselective gold-catalyzed hydration of CF3-
and SF5-alkynes is described. The corresponding trifluoromethylated
and pentasulfanylated ketones are obtained in up to 91% yield as single
regioisomers showcasing the use of CF3 and SF5 as highly efficient directing groups in this reaction. Notably,
this transformation represents the first use of CF3- and
SF5-alkynes in gold catalysis.
Herein, we report a highly regioselective gold-catalyzed formal hydration of propargylic gem-difluorides. Not only does this transformation provide access to versatile fluorinated building blocks that were difficult or hardly possible to access beforehand, but it also represents a rare case of a highly regioselective gold-catalyzed hydroalkoxylation of internal alkynes and puts forward the utility of the difluoromethylene unit as a directing group in catalysis.
The superior nucleofuge character of chlorine over fluorine was taken advantage of in the selective SN2' substitution reaction of gem-chlorofluoropropenes, allowing for the clean formation of β-substituted monofluoroalkenes under metal-free conditions. Numerous N-, S-, O-, and C-nucleophiles behaved nicely in this system. Further synthetic transformations of selected monofluoroalkenes were also accomplished.
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