HFIP-catalyzed direct dehydroxydifluoroalkylation of benzylic and allylic alcohols with difluoroenoxysilanes

Hexafluoroisopropanol (HFIP)-catalyzed direct dehydroxydifluoro-alkylation of benzylic and allylic alcohols with difluoroenoxysilanes is developed. This procedure enables the synthesis of a broad range of alpha,alpha-difluoroketones, a class of highly valuable intermediates and building blocks in medicinal and organic chemistry. Here, we have demonstrated for the first time that HFIP could act as a powerful catalyst for fluorinated carbon-carbon bond formation. The application of this protocol in late-stage dehydroxydifluoroalkylation of potentially bioactive drugs and natural products has also been carried out.

Automated summary

A novel method catalyzed by HFIP for the synthesis of various α,α-difluoroketones has been developed, which are important intermediates in medicinal and organic chemistry. Moreover, this method can also be applied in the late-stage dehydroxydifluoroalkylation of compounds.