One-Pot Synthesis of Heteroatom-Bridged Cyclic Diaryliodonium Salts.

Two one-pot procedures for the construction of O - and N -bridged diaryliodonium triflates are described. An effective aryne-mediated arylation of o -iodophenols and -sulfonamides provides diarylether and diarylamine intermediates, which are subsequently oxidized and cyclized to the corresponding diaryliodaoxinium and -iodazinium salts. Different derivatizations were applied to demonstrate their capacity as useful building blocks and gain a deeper understanding toward the general reactivity of these underdeveloped but potentially highly useful compounds.