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

ABSTRACT: 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.

SUBMITTER: Matsumura M 

PROVIDER: S-EPMC11243167 | biostudies-literature | 2024 Jul

REPOSITORIES: biostudies-literature