Visible-light-induced iron-catalyzed synthesis of N-aryl amides from nitroarenes and chloroalkanes

Abstract

An unprecedented straightforward reductive amidation of chloroalkanes with nitroarenes was readily accomplished by merging iron catalysis with visible-light photoredox catalysis. A variety of commercially inexpensive abundant nitroarenes and chloroalkanes were utilized directly for the preparation of diverse N-aryl amides under environmentally benign mild conditions. This protocol featured an avoidance of exogenous reductant and photocatalyst, simple manipulations, low cost, high step economy and good functional group tolerance. Moreover, during a preliminary investigation of the reaction mechanism, nitrone was isolated and identified as a possible active intermediate, which suggested the involvement of a successive two-step rearrangement in the catalytic cycle.