The synthesis of bioactive amides has been the pursuit of chemists. Herein secondary amides incorporated with an aldehyde group were first generated using aldehydes and secondary amines. Various (hetero)aryl aldehydes and even aliphatic aldehydes (>40 examples) were converted into the desired products in moderate to excellent yields (up to 89%). A plausible mechanism involving a Cu(I/II/III) catalytic cycle combined with radical rearrangement was proposed and confirmed with four key intermediates detected by high-resolution mass spectrometry.