Nucleophilic fluorination of alkynyliodonium salts by alkali metal fluorides: access to fluorovinylic compounds

Fluorovinylic compounds were synthesized by a one-pot procedure from the corresponding alkynyliodonium salts and alkali metal fluorides. Different reaction parameters, such as the temperature, the solvent and the reaction time were examined, and interestingly CsF was chosen for regio- and stereo-selective reactions leading to different alkenyliodonium salts in good yields. Their reduction using NaBH4 provided the corresponding 2-fluorovinylic products quantitatively.