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

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.