The copper-catalyzed chalcogenoamination of 2-alkynylanilines with dichalcogenides has been achieved under mild reaction conditions using the weak base Cs2CO3 in combination with air oxidant, providing a convenient and efficient method for synthesis of 3-sulfenylindoles and 3-selenylindoles, including complex products bearing two attached 3-sulfenylindole rings.The copper-catalyzed chalcogenoamination of 2-alkynylanilines with dichalcogenides has been established, providing a convenient and efficient method for synthesis of 3-sulfenylindoles and 3-selenylindoles, including complex products bearing two attached 3-sulfenylindole rings.