An efficient copper-catalyzed cyclization cascade approach towards highly functionalized methylene 4-chromanol and aurone derivatives has been developed from reactions of ynols via 6-exo-dig and 5-exo-dig cyclization respectively. The catalysis involves alkyne activation via diorgano-diselenides and also their regioselective incorporation into the methylene 4-chromanol and aurone derivative core and is an open-air transformation.