Iodoazidation of Alkenes by Using Iodine Pentafluoride–Pyridine–Hydrogen Fluoride and Trimethylsilyl Azide

Iodoazidation of alkenes was carried out by using iodine pentafluoride-pyridine-hydrogen fluoride and trimethylsilyl azide. In the reactions of terminal alkenes, anti-Markovnikov products were formed selectively. Cyclohexene gave a mixture of cis- and trans-adducts. These results suggest the involvement of radical species in the reaction.