Variation of directing groups on the benzamides for the iridium-catalyzed amidation with tosyl azide (2a) as amino source^a.

^aReaction conditions: N-substituted benzamide 4a–4f (0.40 mmol, 1.0 equiv.), tosyl azide 2a (0.60 mmol, 1.5 equiv.), [IrCp*Cl₂]₂ (5.0 mol%), AgNTf₂ (20 mol%), in [BMIM]PF₆ (0.60 mL, 0.67 M) as reaction medium at 40 °C for 8 h in the open air, isolated yield reported after purification by flash column chromatography on silica gel.

^bND = not detected.