KIO3-Catalyzed C(sp(2))-H Bond Selenylation/Sulfenylation of (Hetero)arenes: Synthesis of Chalcogenated (Hetero)arenes and their Evaluation for Anti-Alzheimer Activity

Author(s)

Rodrigues, Janh ^[1] ; Saba, Sumbal ^[1] ; Joussef, Antonio C. ^[1] ; Rafique, Jamal ^{[1, 2]} ; Braga, Antonio L. ^[1]

Affiliation

^[1] Univ Fed Santa Catarina, Dept Quim, BR-88040900 Florianopolis, SC - Brazil

^[2] Univ Fed Mato Grosso do Sul UFMS, Inst Quim, BR-79074460 Campo Grande, MS - Brazil

• Document type: Journal article
• Source: ASIAN JOURNAL OF ORGANIC CHEMISTRY; v. 7, n. 9, p. 1819-1824, SEP 2018.
• Web of Science Citations: 4

Abstract

Highly efficient KIO3-catalyzed chalcogenations (S and Se) of (hetero)arenes, with easily accessible and odorless dichalcogenides, were obtained through direct C(sp(2))-H bond chalcogenation. Using this benign, atom-economic protocol, the desired products were obtained regioselectively in good to excellent yields in the presence of ethylene glycol (4 equiv.) and KIO3 (20 mol%) as a non-toxic and easily handled catalyst. This metal- and solvent-free approach is scalable, and it is applicable to different types of (hetero)arenes. Furthermore, several of these chalcogenated (hetero)arenes exhibited a significantly high percentage of AChE inhibition, revealing their potential anti-Alzheimer activity. (AU)

• FAPESP's process: 14/50249-8 - Green chemistry: sustainable synthetic methods employing benign solvents, safer reagents, and bio-renewable feedstock
• Grantee: Arlene Gonçalves Corrêa
• Support Opportunities: Research Grants - Research Centers in Engineering Program