A novel hypervalent iodine reagent prepared from o-iodosylbenzoic acid and trifluoromethanesulfonic acid preparation and reactions of alkynyl(o-carboxyphenyl)iodonium triflates

Article abstract of DOI:10.1016/0040-4039(94)02459-O

A hyervalent iodine reagent prepared from o-iodosylbenzoic acid and trifluoromethanesulfonic acid (TfOH) (1:2) showed a high reactivity toward aromatic substrates, giving aryl(o-carboxyphenyl)iodonium triflates in good to high yields. Treatment of the iodine reagent with 1-trimethylsilylalkynes afforded alkynyliodonium triflates bearing carboxy group in high yields. The alkynyliodonium triflates indicated a high efficiency as a Michael acceptor to nucleophiles and the o-carboxyphenyliodonio group behaved as a good leaving group.