Cathodically activated nucleophilic aromatic substitution of hydrogen: a novel electrochemical mechanism

Abstract

Cathodically activated nucleophilic aromatic substitution of hydrogen (S_NAr^H) is reported for the first time; the 1,3,5-trinitrobenzene radical anion reacts with the nucleophile N-methylformamide leading to high yields of the σ^H-complex radical anion; this intermediate can be easily oxidised electrochemically by means of a three-electron mechanism giving rise to the nucleophilic aromatic substitution product (NASH product) in good yield.