Chemo- and site-selective functionalization of phenols offers a rapid strategy for the synthesis of phenol derivatives with diverse structures. Herein, we report a Pd-catalyzed regioselective C-H bond allylic alkylation of phenols with 1,3-dienes, which has precision reactivity at the ortho C-H bond of 2-naphthols, 1-naphthols, and electron-rich phenols. The reaction is accelerated by a diphosphine ligand, does not need any other additive, and features broad substrate scope and good chemo- and regioselectivity. In addition, we have also investigated the asymmetric variant, and the product could be achieved in up to 55% ee.