ChemInform Abstract: Apparent Electrophilic Fluorination of 1,3‐Dicarbonyl Compounds Using Nucleophilic Fluoride Mediated by PhI(OAc)₂.

Abstract

Optimized procedures are developed for the fluorination of 2-substituted ring systems and for di-or monofluorination of unsubstituted chains. In all cases, the NEt 3·3HF/Ph-I(O-Ac)2 combination works with optimal results and the protocol is compatible with a gram-scale access. Product (Xb) is isolated as the hydrate. The usefulness of (XIIb) as precursor of fluorinated heterocycles is demonstrated with the synthesis of pyridone (XIV). The mechanism of the halogenation including all complex side reactions is investigated and discussed in detail. -(NASH, T. J.; PATTISON*, G.; Eur.