Stereoselective Synthesis of (Z)-2-Fluoro-1-alkenyl(phenyl)iodonium Tetrafluoroborates

(Z)-2-Fluoro-1-alkenyl(phenyl)iodonium salts were stereoselectively prepared by the reaction of alkynyl(phenyl)iodonium salts with aqueous HF in good yields. The method is applicable to the synthesis of fluoroalkenyliodonium salts having functional groups such as ketone, ester, and chloride. (Z)-2-Fluoro-1-alkene, (Z)-2-fluoro-2-alkenoate, and (Z)-β-fluoroenyne could be stereoselectively prepared from the fluoroalkenyliodonium salt.