Visible-Light-Induced Difunctionalization of Styrenes: Synthesis of <i>N</i>-Hydroxybenzimidoyl Cyanides

Abstract

A visible-light-induced synthesis of <i>N</i>-hydroxybenzimidoyl cyanides from aromatic terminal alkenes is achieved by using Eosin Y as an organic photoredox catalyst. The process goes via a radical pathway with successive incorporation of two nitrogen atoms, one each from <i>tert</i>-butyl nitrite and ammonium acetate. The final product is achieved by the concomitant installation of an oxime and a nitrile group. DFT calculation supports a biradical pathway and all the proposed steps. A few useful synthetic transformations of <i>N</i>-hydroxybenzimidoyl cyanide are also illustrated.