In this work, we demonstrated the systematic synthesis of pseudocyclic and cyclic TIPSethynyl NHIs via a one-pot procedure, which revealed a wide range of different heterocycles and substituents to be suitable. The reactivity of those ENHIs was investigated in inter-and intramolecular group transfer reactions, which showed a comparable reactivity to TIPS-EBX. It further enables access to novel N-substituted heteroaromatic compounds and bi-triazole motives. Other promising applications of N-heteroaromatic substituted-λ 3 -iodanes are under current work in our laboratory.