A new bidentate directing group, 3-amino-1-methyl-1H-pyridin-2-one, is introduced to achieve a powerful PdII metallacycle for selective γ-C(sp3)-H activation and arylation of aromatic and aliphatic carboxylic acid derivatives. The versatility of the directing group is validated for remote arylation of β-C(sp3)-H, β-C(sp2)-H, and γ-C(sp2)-H to achieve therapeutically important 2-pyridone analogues and arylated acid synthons. The traceless removal of the directing group to retrieve the directing element and carboxylic acids makes this method more interesting. © Copyright 2018 American Chemical Society.