We chose to investigate the reaction of 2-bromo-N-phenyl benzamide 1a, primarily because of the potential amidedirected C-H activation of the N-phenyl moiety. Given the ability for a range of Pd pre-catalysts and monodentate ligands to catalyze the formation of phenanthridinones 2 (Scheme 1), we planned to assess the ability of bidentate ligands to affect the transformation, particularly as their characterization in follow-on mechanistic studies (i.e. stochiometric experiments with Pd) might be more facile. An initial pre-catalyst and ligand screen (see supporting information for full details) showed that 5 mol% Pd(OAc)2 {formally high purity Pd3(OAc)6, nitrite-free} and dppe, with K2CO3 as base in DMF at 80 °C gave N-phenyl phenanthridinone 2a in 58% yield (Scheme 3A). Furuta / Kan 8b and Fu / Chen 8g obtained 2a in 23% and 80% yield respectively from 1a. Crucially, for application to HTE, this reaction was found to be tolerant of air. Conducting the reaction under anhydrous and oxygen-free conditions gave a yield of 2a which was 54%.