A palladium-catalyzed [4+1] cycloaddition of prop-2-yn-1-ones with double isocyanides is developed herein. The transformation worked well to produce a series of 2-amino-4-cyanofurans with high efficiency and a broad reaction scope. Based on mechanism studies, it is believed that the palladium-catalyzed [4+1] imidoylative cycloaddition of prop-2-yn-1-ones was concerted. Treated with aryl amine and H2O, the [4+1] cycloaddition of prop-2-yn-1-ones with double isocyanides provided 2-amino-4-amidylpyrroles efficiently.