Cathodically activated nucleophilic aromatic substitution of hydrogen: a novel electrochemical mechanism.
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.
Gallardo
Iluminada
I
Departament de Química, Universitat Autònoma de Barcelona, 08193-Bellaterra Barcelona, Spain. Iluminada.Gallardo@uab.es
Guirado
Gonzalo
G
Marquet
Jordi
J