We have developed a novel palladium-catalyzed method for synthesizing quinolinyl lactones via double C(sp3)-H functionalization. This atom-economical strategy utilizes a bifunctional 2-iodobenzoic acid reagent in a single catalytic cycle. An optimized solvent mixture of hexafluoro-2-propanol and acetic acid significantly enhanced reactivity and selectivity. This work provides a valuable, site-selective pathway for creating complex quinolinyl lactone scaffolds.