A novel ligand propan-2-one O-(p-tolylcarbamoyl) oxime (L7) has been developed to promote C(sp2)-H olefination of benzoic acids and phenylacetic acids via a palladium catalyst. With the subsequent lactonization of the olefinated products through 1,4-addition, highly monoselective cyclic lactone products of benzofuranones and benzopyrones were obtained in moderate to excellent yields. The DFT calculation demonstrated that the novel ligand propan-2-one O-(p-tolylcarbamoyl) oxime (L7) could improve the C-H activation reaction to give cyclic lactone products elegantly.