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. 2013 Jun 13:9:1141-7.
doi: 10.3762/bjoc.9.127. Print 2013.

Photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides

Yohsuke Kobiki  1 , Shin-Ichi Kawaguchi, Takashi Ohe, Akiya Ogawa
Affiliations

Photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides

Yohsuke Kobiki et al. Beilstein J Org Chem. .

Abstract

A novel method of photoinduced synthesis of unsymmetrical diaryl selenides from triarylbismuthines and diaryl diselenides has been developed. Although the arylation reactions with triarylbismuthines are usually catalyzed by transition-metal complexes, the present arylation of diaryl diselenides with triarylbismuthines proceeds upon photoirradiation in the absence of transition-metal catalysts. A variety of unsymmetrical diaryl selenides can be conveniently prepared by using this arylation method.

Keywords: arylation; free radical; organobismuth; photoinduced reaction; unsymmetrical diaryl selenide.

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Figures

Scheme 1
Scheme 1
Photoinduced radical reaction of diaryl diselenide with triphenylbismuthine.
Scheme 2
Scheme 2
Photoinduced reaction of diphenyl disulfide with triphenylbismuthine.
Scheme 3
Scheme 3
A plausible reaction pathway for the photoinduced reaction of diaryl diselenide with triarylbismuthine.
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