L,X-type transient directing groups (TDG) based on a reversible imine linkage have emerged as broadly useful tools for C-H activation of ketones and free amines. However, competitive binding interactions among multiple reaction components (TDG itself, substrate, and substrate-TDG adduct) with the palladium catalyst often lead to the formation of multiple unreactive complexes, rendering ligand development extremely challenging. Herein we report the finding of versatile 2-pyridone ligands that addresses these problems and significantly improves the gamma-methylene arylation of alkyl amines, extending the coupling partners to a wide range of medicinally important heteroaryl iodides and even previously unreactive heteroaryl bromides. The combination of an appropriate transient directing group and pyridone ligand has also enabled the delta-arylation of alkyl amines. Notably, our transient directing group design reveals the importance of matching the size of the Pd-chelation with different transient directing groups and the size of palladacycles generated from gamma- and delta-C-H bonds: TDGs that coordinate with Pd(II) to form a six-membered chelate are selective toward gamma-C-H bonds, whereas TDGs that coordinate with Pd(II) via a five-membered chelate tend to activate delta-C-H bonds. These findings provide an avenue for developing protecting group free and selective C-H functionalization using the transient directing group strategy.