The chemistry of hypervalent iodine compounds, in particular aryl-λ 3 -iodanes, is versatile, and a wide range of applications is meanwhile established in organic synthesis. They can be applied as mild oxidants, in phenol dearomatizations or in α-oxygenation reactions. In a complemental reactivity, diaryliodonium salts are potent electrophilic aryl donors. Their cyclic, iodolium derivatives have a proven utility as precursors for the synthesis of hetero-and carbocycles , and their pronounced σ-holes render them efficient halogen-bond donors (XB-donors in XBcatalysis). Despite their great potential in organic synthesis and catalysis, their structural variation is still limited. In particular heteroarene-bridged cyclic iodonium salts are rare. Examples include the benzisoxazole-containing iodonium salt 1 described by Lisichkina and Tolstaya 1 (Figure ). Our group is interested in the chemistry of hypervalent iodine species in all their variety, particularly those containing N-heterocycles either as tethered stabilizing ligands or as an inclusive part of a cyclic iodonium salt. We prepared five-membered, N-heterocycle-containing iodoliums 2 and investigated their reactivity and utility in XB-catalysis. We also established onepot methods for generating six-membered carbon-, oxygen-and nitrogen-bridged iodonium salts, such as the iodazinium triflate 3. Based on these promising findings, we further want to elaborate this chemistry and herein present the first synthesis and application of more sophisticated imidazo-and pyrazoloiodazinium salts.