Nucleophilic vinylic substitutions of (Z)-(2-aroyloxyvinyl)phenyl-λ-iodanes with tetrabutylammonium halides: vinylic SN2 reactions and ligand coupling on iodine(III)

Treatment of (Z)-(β-benzoyloxyvinyl)phenyl-λ³-iodanes, readily prepared from ethynyl(phenyl)(tetrafluoroborato)-λ³-iodane via stereoselective Michael-type addition of benzoic acids in methanol in the presence of sodium benzoates, with tetrabutylammonium halides in THF at 65 °C results in a vinylic S_N2 reaction to give the inverted (E)-β-benzoyloxyvinyl halides in high yields.