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

Autor:	Rios EAM; Department of Chemistry, Laboratory of Polymers and Catalysis (LaPoCa), Federal University of Paraná - UFPR P. O. Box 19061 Curitiba PR 81531-990 Brazil danielrampon@ufpr.br., Gomes CMB; Department of Chemistry, Laboratory of Polymers and Catalysis (LaPoCa), Federal University of Paraná - UFPR P. O. Box 19061 Curitiba PR 81531-990 Brazil danielrampon@ufpr.br., Silvério GL; Department of Chemistry, Laboratory of Polymers and Catalysis (LaPoCa), Federal University of Paraná - UFPR P. O. Box 19061 Curitiba PR 81531-990 Brazil danielrampon@ufpr.br., Luz EQ; Department of Chemistry, Laboratory of Polymers and Catalysis (LaPoCa), Federal University of Paraná - UFPR P. O. Box 19061 Curitiba PR 81531-990 Brazil danielrampon@ufpr.br., Ali S; University of São Paulo, Faculty of Animal Science and Food Engineering Pirassununga SP Brazil., D'Oca CDRM; Department of Chemistry, Laboratory of Polymers and Catalysis (LaPoCa), Federal University of Paraná - UFPR P. O. Box 19061 Curitiba PR 81531-990 Brazil danielrampon@ufpr.br., Albach B; Health Department, Unicesumar - The University Center of Maringá Curitiba PR 81070-190 Brazil., Campos RB; Departamento Acadêmico de Química e Biologia, Universidade Tecnológica Federal do Paraná Rua Deputado Heitor de Alencar Furtado, 5000 81280-340 Curitiba Brazil., Rampon DS; Department of Chemistry, Laboratory of Polymers and Catalysis (LaPoCa), Federal University of Paraná - UFPR P. O. Box 19061 Curitiba PR 81531-990 Brazil danielrampon@ufpr.br.
Jazyk:	angličtina
Zdroj:	RSC advances [RSC Adv] 2023 Jan 04; Vol. 13 (2), pp. 914-925. Date of Electronic Publication: 2023 Jan 04 (Print Publication: 2023).
DOI:	10.1039/d2ra06813c
Abstrakt:	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. Competing Interests: There are no conflicts to declare. (This journal is © The Royal Society of Chemistry.)
Databáze:	MEDLINE
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