Palladium-catalyzed regio- and diastereoselective allylic alkylations using ionic liquids (ILs) as a solvent were demonstrated. The reaction using diethyl(2-methoxyethyl)methylammonium bis(trifluoromethanesulfonyl)amide ([N-221ME][NTf2]) or ethylhexyldimethylammonium bis(trifluoromethanesulfonyl)amide ([N-6211][NTf2]) as solvent realized the recyclable use of the palladium catalyst while maintaining excellent regioselectivity and diastereoselectivity.