Synthesis of Arylbenziodoxoles Using Pseudocyclic Benziodoxole Triflate and Arenes

An acid activated pseudocyclic hypervalent iodine reagent, 2-[hydroxy(trifluoromethanesufonyloxy)]iodobenzoic acid, can easily react with various arenes in the presence of trifluoromethanesulfonic acid to produce pseudocyclic diaryliodonium triflate salts. This synthetic procedure proceeds under mild conditions to afford the respective iodonium salts in moderate to good yields. Several pseudocyclic diaryliodonium triflate salts structures have been confirmed by X-ray crystallography. Obtained products can be easily converted to cyclic hypervalent iodine(III) compounds, arylbenziodoxolones, in moderate to good yields under basic conditions.