Nucleophilic vinylic substitutions of (Z)-(2-aroyloxyvinyl)phenyl-λ3-iodanes with tetrabutylammonium halides: vinylic SN2 reactions and ligand coupling on iodine(III)

Exposure of (Z)-(β-benzoyloxyvinyl)phenyl-λ3-iodanes to n-Bu4NX in THF at 65 °C results in a vinylic SN2 reaction to give the inverted (E)-vinyl halides in high yields.