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 towards the general reactivity of these underdeveloped but potentially highly useful compounds.