Synthesis of Five-Membered Iodine–Nitrogen Heterocycles from Benzimidazole-Based Iodonium Salts

Pseudocyclic 2-benzimidazolyl-substituted diaryliodonium salts were obtained by the reaction of the corresponding [hydroxy­(tosyloxy)­iodo]­arenes with arenes in the presence of trifluoromethanesulfonic acid. X-ray structural analysis of these iodonium salts confirmed their pseudocyclic structure with a short (2.57–2.58 Å) noncovalent I···N interaction. Treatment of 2-benzimidazolyl-substituted diaryliodonium triflates with a base afforded novel five-membered iodine–nitrogen heterocycles.采用相应的[羟基(对甲苯磺酰氧基)碘]芳烃与芳烃在三氟甲磺酸存在下发生反应，可制备得到假环化2-苯并咪唑基取代二芳基碘鎓盐。对这类碘鎓盐的X射线结构分析证实了其具有假环化结构，且存在短程（2.57~2.58 Å）非共价I···N相互作用。将2-苯并咪唑基取代二芳基碘鎓三氟甲磺酸盐与碱反应，可得到新型五元碘氮杂环。