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 σH-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. © 2002 The Royal Society of Chemistry.
|Publication status||Published - 1 Jan 2002|
Gallardo, I., Guirado, G., & Marquet, J. (2002). Cathodically activated nucleophilic aromatic substitution of hydrogen: A novel electrochemical mechanism. Chemical Communications, 2(22), 2638-2639. https://doi.org/10.1039/b207168a