Because of fluorine’s unique properties, the selective substitution of hydrogen by fluorine constitutes a key strategy in drug discovery and material research. But common fluorination reagents including nucleophilic fluorinating reagents (e.g., HF based reagents, DAST) and electrophilic regents (e.g. NFSI and Selectfluor) are ether expensive, corrosive, toxic, and often have very poor atom-economy. So expansion of use of alkali metal fluorides to other fluorination reactions like addition reaction are highly desired. Positron emission tomography (PET) based on radioactive fluorine isotope (18F) becomes increasingly important in diagnosis and drug discovery. But introduction of 18F to an organic molecular is still challenging. Here,we report a widely applicable, highly efficient synthesis of fluoroenamides and radio fluoroenamides. Our fluorine source is the most economical base on hydrogen bonding clusters KF/HFIP system. The reactions exhibited high functional groups tolerance at ambient atmosphere and provides an remarkable rout to 18F label biomolecules.

Nucleophilic (radio)fluoro-click reaction enabled by of hydrogen bonding clusters

254th National Meeting (2017)

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