T. Kitamura
1995
Citations
0
Influential Citations
45
Citations
Journal
Journal of Synthetic Organic Chemistry Japan
Abstract
Highly reactive hypervalent organoiodine reagents were prepared from iodosylbenzene (PhIO) or iodobenzene diacetate [PhIO (IAc)2] by using the activating agents such trifluoromethanesulfonic acid or the anhydride. The reagents [PhIO-TfOH] and [PhI(OAc),-2 TfOH] showed a high reactivity toward unsaturated substrates : aromatics, alkenes, and alkynes. Reaction of PhIO with double the molar quantity of TfOH gave a (pphenylene) bisiodine ( III )reagent, 1[ (hydroxy) (trifyloxy)iodo]-4[ (phenyl) (trifyloxy)iodo] benzene, which also indicated an excellent reactivity toward unsaturated substrates. O-Iodosylbenzoic acid was activated by TfOH to afford a reactive iodine ( III )reagent. The high reactivity of the present organoiodine ) III reagents was useful in organic synthesis, specially preparation of functionalized iodonium salts . The prepared alkynyliodonium salts and [ O(trimethylsilyl) phenyl] iodonium salts were found to be especially accessible to organic synthesis.