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.
Synthesis of Five-Membered Iodine–Nitrogen Heterocycles from Benzimidazole-Based Iodonium Salts
J. Org. Chem. 2018, 83 (19), 12056–12070, DOI: 10.1021/acs.joc.8b01995.