Organocatalytic methods that allow the construction of C–F bonds are so far restricted on electrophilic fluorination. Despite the fact that nucleophilic sources of fluorine are cost-effective and by far the most accessible, <i>organocatalytic nucleophilic fluorination </i>remains a challenge. With the long term aim to bring new solutions in the field of catalysis, we took inspiration from the naturally occurring fluorinase enzyme capable of mediating C–F bond formation <i>via</i> nucleophilic fluorination with fluoride. Hydrogen bonding (HB) with fluoride is a key interaction encountered when analyzing the mode of action of 5'-fluoro-5'-deoxyadenosine synthase. This observation led us to investigate the effect of HB on fluoride reactivity. Our group has previously reported the effect of HB on the structure and reactivity of complexed fluoride and disclosed a library of novel urea-fluoride complexes which were characterized in solid state and solution. This presentation will describe our most recent advances in the field and our approach towards the discovery of a novel mode of catalysis for enantioselective nucleophilic fluorination with alkali metal fluorides.

Hydrogen bonding mediated asymmetric nucleophilic fluorination

256th National Meeting (2018)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.