Issue 2, 2023

Silver-catalyzed direct selanylation of indoles: synthesis and mechanistic insights

Abstract

Herein we describe the Ag(I)-catalyzed direct selanylation of indoles with diorganoyl diselenides. The reaction gave 3-selanylindoles with high regioselectivity and also allowed direct access to 2-selanylindoles when the C3 position of the indole ring was blocked via a process similar to Plancher rearrangement. Experimental analyses and density functional theory calculations were carried out in order to picture the reaction mechanism. Among the pathways considered (via concerted metalation–deprotonation, Ag(III), radical, and electrophilic aromatic substitution), our findings support a classic electrophilic aromatic substitution via Lewis adducts between Ag(I) and diorganoyl diselenides. The results also afforded new insights into the interactions between Ag(I) and diorganoyl diselenides.

Graphical abstract: Silver-catalyzed direct selanylation of indoles: synthesis and mechanistic insights

Supplementary files

Article information

Article type
Paper
Submitted
28 okt 2022
Accepted
17 dek 2022
First published
04 yan 2023
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2023,13, 914-925

Silver-catalyzed direct selanylation of indoles: synthesis and mechanistic insights

E. A. M. Rios, C. M. B. Gomes, G. L. Silvério, E. Q. Luz, S. Ali, C. D. R. M. D'Oca, B. Albach, R. B. Campos and D. S. Rampon, RSC Adv., 2023, 13, 914 DOI: 10.1039/D2RA06813C

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