In conclusion, we developed an aryne-based one-pot procedure for the synthesis of iodaoxinium and iodazinium triflates. Initiated by an aryne-mediated metal-free O-or N-arylation followed by an oxidative cyclization, a variety of o-iodophenols and sulfonamides were successfully transformed into diaryliodaoxinium and diaryliodazinium triflates in high yields. With further derivatizations, a wide range of applications of these mostly unknown iodonium salts was demonstrated. Further derivatizations should be developed for heteroatom-bridged iodonium salts, since they have an altered, albeit interesting reactivity compared to their pure carbon analogs.