Molecules (Jul 2024)

Bismuth(III)-Catalyzed Regioselective Selenation of Indoles with Diaryl Diselenides: Synthesis of 3-Selanylindoles

  • Mio Matsumura,
  • Airi Umeda,
  • Yuika Sumi,
  • Naoki Aiba,
  • Yuki Murata,
  • Shuji Yasuike

DOI
https://doi.org/10.3390/molecules29133227
Journal volume & issue
Vol. 29, no. 13
p. 3227

Abstract

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Heterocyclic aryl selenides have recently attracted considerable research interest owing to their applications in biological and pharmaceutical fields. Herein, we describe a simple and general synthesis of 3-selanylindoles via a novel regioselective C–H selenation of indoles using a bismuth reagent as a catalyst. The reactions of indoles with diselenides in the presence of 10 mol% BiI3 at 100 °C in DMF afforded the corresponding 3-selanylindoles in moderate-to-excellent yields. The reaction proceeded efficiently under aerobic conditions by adding only a catalytic amount of BiI3, which was non-hygroscopic and less toxic, and both selanyl groups of the diselenide were transferred to the desired products.

Keywords