A palladium(II)-catalyzed regioselective syn-hydroarylation reaction of homopropargyl amines has been developed, wherein-selectivity is controlled by a cleavable bidentate directing group: Under the optimized reaction conditions, both dialkyl and alkylaryl substrates were found to undergo hydroarylation with high selectivity. The products of this reaction contain a 4,4-disubstituted homoallylic amine motif that is commonly seen in drug molecules and other bioactive compounds.