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.