A versatile Cu-catalyzed direct ortho-C(sp2)-H amination of benzamides and picolinamides with alkylamines has been achieved. This method employs cheap and eco-friendly copper as a catalyst and oxygen as an oxidant, and also has the advantages of straightforward steps and excellent functional group compatibility. Further application of our approach was demonstrated by the synthesis of TCMDC-125116, SPHINX, and SRPIN340.