An efficient synthesis of dihydro-isoquinolines via a Pd-catalyzed double C-H bond [a C(sp2)-H and a C(sp3)-H bond] activation/annulation (CHAA) reaction is presented. This methodology features a short reaction time, high atom economy (loss of H2O only) and the formation of a sterically less favoured tertiary C-N bond. This fast (30 min) and environmentally benign radical C-H activation approach has demonstrated the potential direction for the future design/development of fast and efficient C-H direct functionalization processes.