Two new solid pyridinium salt supported HTIB reagents (N-{4-[hydroxyl(tosyloxy)iodo]benzyl}pyridinium tetrafluoroborate and N-{4-[hydroxyl(tosyloxy)iodo]phenylcarbamoylmethyl}pyridinium tetrafluoroborate) were synthesised using a pyridinium salt as a cationic support. Although the former was hygroscopic the latter was stable in air and in a highly humid atmosphere over a few weeks. The latter has an extra amide linkage. The structures of both compounds were established by IR, 1H NMR, 13C NMR, MS and elemental analysis. Then, two 4-tosyloxy-2-substituted phenols were successfully prepared using the new reagents. Both reagents were easily regenerated in high yields.
