Synthesis of [

This communication reports a method for the vinylogous radiofluorination of α-diazoacetates to generate γ-[(18)F]fluoro-α,β-unsaturated esters and ketones in moderate to good radiochemical yields. The method uses no-carrier-added [(18)F]AgF and is compatible with aromatic and non-aromatic substrates and a number of different functional groups. The labeling method is showcased in the synthesis of a fluorinated 5-cholesten-3-one derivative as well as a difluorinated product pertinent to drug discovery.