Synthesis of novel arylfluorinated cyclic β-amino acid derivatives and β-lactams has been accomplished. Thestudies on the Pd-catalyzed arylfluorination of the ring olefin bond of cyclooctene-fused azetidine-2-one and beta-amino esters with cyclooctene skeleton were performed under versatile experimental conditions. The arylfluorinative difunctionalization of cyclooctene-fused β-lactam, performed with phenylboronic acid, in the presence of Selectfluor, azacyclic ligands, and solvents, gave a separable mixture of various fluorinated and non-fluorinated products. In contrast, arylfluorination of cyclooctane-β-amino esters proceeded under similar conditions, with full regio- and stereoselective manners leading to a sole phenyl-fluorinated compound. Possible synthetic pathways regarding the outcome of these types of transformation are also proposed.