Abstract
Galvanostatic electrolysis of chiral 2-(methylsulfinyl) 1H-benzimidazole in an acetonitrile/tetraethyl ammonium tetrafluoroborate system has been exploited to carry out the selective N-alkylation of the benzimidazole moiety with organohalides, thus obtaining chiral derivatives with potential use in drug research. Theoretical determination of the redox potential for the title compound has been effected, and plausible pathways for its electroactivation have been described. Furthermore, by means of this electrochemical strategy, the access to enantioenriched N-alkylated 2-(methylsulfinyl)benzimidazole has been established.
GRAPHICAL ABSTRACT
SUPPLEMENTAL MATERIAL
1H NMR and 13C NMR data, HPLC traces, apparatus, and computational details for this article can be accessed on the publisher’s website.