Activation of perfluoroalkyl iodides by anions: extending the scope of halogen bond activation to C(sp³)–H amidation, C(sp²)–H iodination, and perfluoroalkylation reactions

Abstract

A simple, efficient, and convenient activation of perfluoroalkyl iodides by <i>t</i>BuONa or KOH, without expensive photo- or transition metal catalysts, allows the promotion of versatile α-sp³ C-H amidation reactions of alkyl ethers and benzylic hydrocarbons, C-H iodination of heteroaryl compounds, and perfluoroalkylations of electron-rich π bonds. Mechanistic studies show that these novel protocols are based on the halogen bond interaction between perfluoroalkyl iodides and <i>t</i>BuONa or KOH, which promote homolysis of perfluoroalkyl iodides under mild conditions.