Nucleophilic vinylic substitutions of (Z)-(2-aroyloxyvinyl)phenyl- λ3-iodanes with tetrabutylammonium halides: Vinylic S N2 reactions and ligand coupling on iodine(III)

Article abstract of DOI:10.1016/j.tetlet.2005.01.101

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.