Electrochemically Induced N-Alkylation of Chiral 2-(Methylsulfinyl) 1H-Benzimidazole

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

Keywords:

• Electrosynthesis
• N-alkylation
• 2-sulfinyl benzimidazoles
• sulfoxides

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.