Fluorinated organic molecules display broad utility as valuable pharmaceuticals, radiotracers, performance materials, and agrochemicals. While catalytic asymmetric methods using electrophilic �F+� equivalents have been identified, complementary strategies for enantioselective C�F bond formation using abundant, inexpensive nucleophilic fluoride sources are scarce. We have developed catalytic methods for the synthesis of fluorinated building blocks using benzoyl fluoride as a soluble, latent source of fluoride anion. The combination of benzoyl fluoride and an alcohol generates HF in situ, enabling catalyst-controlled hydrofluorination. I will discuss the application of this strategy to the asymmetric catalytic ring opening of epoxides and aziridines to provide �-fluoroalcohols and �-fluoroamines, as well as the enantioselective bromofluorination of unactivated alkenes. Mechanistic studies have shed light on the identity of the active nucleophilic species and enabled synthetic improvements.

Catalytic strategies for asymmetric nucleophilic fluorination using a latent HF source

244th National Meeting (2012)

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