Copper-catalyzed Csp-chalcogen bond formation: Versatile approach to N-(3-(organochalcogenyl)prop-2-yn-1-yl)amides

Abstract

Abstract This work describes the copper-catalyzed C sp -chalcogen bond formation through cross-coupling reactions of propynylbenzamides and diorganyl dichalcogenides at room temperature, under open atmosphere. Generally, the reactions have proceeded very smoothly, affording the new class of organochalcogen-containing propynylbenzamides in good yields. Notably, this protocol showed to be tolerant to neutral, electron-donating and electron-withdrawing substituents present in both reaction substrates. In addition, the applicability of the carbon-chalcogen bond as a reactive site has been proved by successfully employment of the N -methyl- N -(3-(butylselanyl)prop-2-yn-1-yl)benzamide as a precursor in palladium-catalyzed Suzuki and Sonogashira type reactions.