Iodonium polymer-supported

Iodofluorination reactions of acetylenes can be carried out with iodine fluoride, prepared directly from the corresponding elements,553 with jV-iodosuccinimide in the presence of polymer-supported hydrogen fluoride,258 with (difluoroiodo)mcthane,554 or with bis(pyridine)iodonium tetrafluoroborate in the presence of fluoride.555 Some examples are summarized in Table 45. 

To install the appropriate functionality at C2, solution phase chemistry has relied on a trans-diaxial addition of an iodonium electrophile in the presence of an amine to form an iodosulfonamide. Displacement of iodine proceeds presumably through an aziridine intermediate and may be induced by a thiolate nucleophile to fashion thioethyl 2-amidoglycosyl donors [38]. Successful transfer of this method to the solid support allowed polymer-bound glycals to be converted into thioethyl gly-cosyl donors. These donors were in turn coupled with a variety of glycosyl acceptors, including glycals [39]. 

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