Copper-Catalyzed Three-Component Reaction of Oxadiazoles, Elemental Se/S and Aryl Iodides: Synthesis of Chalcogenyl (Se/S)-Oxadiazoles

Author(s)

Peterle, Marcos M. ^[1] ; Scheide, Marcos R. ^[1] ; Silva, Lais T. ^[1] ; Saba, Sumbal ^[1] ; Rafique, Jamal ^{[2, 1]} ; Braga, Antonio L. ^[1]

Affiliation

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

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

• Document type: Journal article
• Source: CHEMISTRYSELECT; v. 3, n. 46, p. 13191-13196, DEC 13 2018.
• Web of Science Citations: 2

Abstract

An efficient copper-catalyzed three-component chalcogenation of oxadiazoles with elemental selenium/sulfur and aryl iodide is described herein. This one-pot C(sp(2))-H bond chalcogenation approach is attractive and practical, since a cheap copper catalyst is employed with minimum catalytic loading, in an open-to-air atmosphere. Under optimized conditions, that reaction provides a wide range of structurally diverse organochalcogenyl (Se/S)-oxadiazoles in good to excellent yields with good functional group tolerance. This practical approach represents a valuable contribution to synthetic and medicinal chemistry, providing an important addition to the current C-Se/S bond formation chemistry scenario. (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