Iodotriflamdation vs. Electrophilic Aromatic Iodination in the Reaction of N‐Phenyltriflamide with Alkenes

Abstract

Reaction of N-phenyltriflamide with styrene, p-chlorostyrene, vinylcyclohexane and a-methylstyrene in oxidative system (t-BuOCl + NaI) gives three types of products: (i) of aromatic iodination of the reagent -N-(4-iodophenyl)triflamide and N-(2,4-diiodophenyl)triflamide; (ii) of oxidative addition of the iodinated reagent to the substrate with different regioselectiv-(iii) of chloro(oxy)iodination of the substrate -2-iodo-1-phenylethanol, 1-chloro-4-(1-chloro-2-iodoethyl)benzene, 1-cyclohexyl-2iodoethanol and 1-iodo-2-phenylpropan-2-ol. Different regioselectivity of iodosulfonamidation for different alkenes and the competition between electrophilic aromatic iodination and iodotriflamidation are explained and the mechanism is proposed based on the results of quantum chemical calculations and the NBO analysis.