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

Eietsu Hasegawa; Kazuma Mori; Shiori Tsuji; Kazuki Nemoto; Taku Ohta; Hajime Iwamoto

doi:10.1071/CH15396

RESEARCH ARTICLE

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

Eietsu Hasegawa ^A ^B , Kazuma Mori ^A , Shiori Tsuji ^A , Kazuki Nemoto ^A , Taku Ohta ^A and Hajime Iwamoto ^A

+ Author Affiliations

- Author Affiliations

^A Department of Chemistry, Faculty of Science, Niigata University, 8050 Ikarashi-2, Nishi-ku, Niigata 950-2181, Japan.

^B Corresponding author. Email: ehase@chem.sc.niigata-u.ac.jp

Australian Journal of Chemistry 68(11) 1648-1652 https://doi.org/10.1071/CH15396
Submitted: 1 July 2015 Accepted: 30 July 2015 Published: 31 August 2015

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.

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

Abstract

References

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