%0 Journal Article %T Synthesis and reactivity of azole-based iodazinium salts. %A Kuczmera TJ %A Dietz A %A Boelke A %A Nachtsheim BJ %J Beilstein J Org Chem %V 19 %N 0 %D 2023 %M 36960303 %F 2.544 %R 10.3762/bjoc.19.27 %X A systematic investigation of imidazo- and pyrazoloiodazinium salts is presented. Besides a robust synthetic protocol that allowed us to synthesize these novel cyclic iodonium salts in their mono- and dicationic forms, we gained in-depth structural information through single-crystal analysis and demonstrated the ring opening of the heterocycle-bridged iodonium species. For an exclusive set of dicationic imidazoiodaziniums, we show highly delicate post-oxidation functionalizations retaining the hypervalent iodine center.