Oxidation reactions of stable chalcogenamides with iodine are intriguing due to their broad application in various organic syntheses. In the present study we report on the utilization of N-heterocyclic carbene and cyclic-alkyl-amino carbenes L1–3: (L1: = :C[N(2,6-iPr2-C6H3)CH]2, L2: = :C(CH2)(CMe2)(C6H10)N-2,6-iPr2-C6H3, L3: = :C(CH2)(CMe2)2N-2,6-iPr2-C6H3) for the syntheses of chalcogenamides L1–3E (E = S, Se, Te) 1–4 and zwitterionic adducts L1–3E–I–I 5–8. The synthesis of compounds 1–4 involved the addition reaction of ligand L1–3: and elemental chalcogen. Treatment of 1–4 with iodine resulted in the formation of adducts 5–8. Compounds 5–8 are well characterized with various spectroscopic methods and single-crystal X-ray structural analysis.
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