Reactions of nucleophiles with nitroarenes: multifacial and versatile electrophiles

Abstract

In this overview, it is shown that there are many initial reactions between nitroarenes and nucleophiles: addition to the electron-deficient ring at positions occupied by halogen and hydrogen atoms, addition to the nitro group, single-electron transfer (SET), and other types of initial reactions. The resulting intermediates react further in a variety of ways to form products of nucleophilic substitution of a halogen atom (SN Ar), a hydrogen atom (SN ArH), and others. Many variants of these processes are briefly discussed, particularly in relation of rates of the initial reactions and further transformations.

Keywords: carbanions; nitroarenes; oxidation; single-electron transfer; vicarious nucleophilic substitution.