Pd(II)-catalyzed addition of sp2 C-H to nitrile/aerobic oxidation sequences for the preparation of functionalized α-imino ketones is described in which readily available heteroarenes and O-acyl cyanohydrins were employed. Various functionalized targeted molecules can be prepared in good yields with high atom and step economy. Moreover, a broad substrate scope and the ready manipulation and availability of the reaction partners enable this protocol to be appealing to explore the chemical space of the construction of functionalized α-imino ketones with high efficiency.