Visible Light-Promoted Metal-Free Reduction of Organohalides by 2-Naphthyl or 2-Hydroxynaphthyl-Substituted 1,3-Dimethylbenzimidazolines

Abstract

The visible light-promoted reduction reactions of some organohalides were investigated using 2-aryl-1,3-dimethylbenzimidazolines (Ar-DMBIH) possessing 2-naphthyl or 2-hydroxynaphthyl substituents. In these reduction reactions, single-electron transfer from photo-excited Ar-DMBIH, attained by Xe lamp irradiation through an appropriate glass-filter (λ > 390 nm), to the halide substrates leads to the carbon–halogen bond cleavage, followed by the rearrangements of the formed carbon radicals such as 5-exo hexenyl cyclization and the Dowd–Beckwith ring expansion. Addition of 1,8-diazabicyclo[5.4.0]undec-7-ene was found to enhance the reducing ability of hydroxynaphthyl-substituted DMBIH. A household white light-emitting diode was also used as a light source for these reactions.