Research Article Details

Article ID: A38011
PMID: 12510275
Source: Chem Commun (Camb)
Title: Cathodically activated nucleophilic aromatic substitution of hydrogen: a novel electrochemical mechanism.
Abstract: Cathodically activated nucleophilic aromatic substitution of hydrogen (SNArH) 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 sigma 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.
DOI: 10.1039/b207168a