Stereospecific synthesis of (E)-alkenyl(phenyl)iodonium tetrafluoroborates via zirconium–iodane exchange

Abstract

Reaction of vinylzirconium with hypervalent phenyliodanes leads to zirconium–iodane exchange in THF at room temperature yielding alkenyl(phenyl)iodonium salts stereoselectively with retention of configuration. Vinyliodonium salts are highly effective as the activated species of vinyl iodides. They reacted with RMgBr in the presence of CuI to afford (E)-1,2-disubstituted alkenes.