Pd(II)-catalyzed intermolecular arylation of unactivated C(sp ³)-H bonds with aryl bromides enabled by 8-aminoquinoline auxiliary

An example of using readily available, less reactive aryl bromides as arylating reagents in the Pd(II)-catalyzed intermolecular arylation of unactivated C(sp³)-H bonds is described. This reaction was promoted by a crucial 8-aminoquinolinyl directing group and a K₂CO₃ base, enabling regiospecific installation of an aryl scaffold at the β-position of carboxamides. A mechanistic study by DFT calculations reveals a C(sp³)-H activation-led pathway featuring the oxidative addition as the highest energy transition state.