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A dearomative C4-allylation of benzyl ammoniums with allylstannanes by a palladium catalysis is described. A triarylphosphine-ligated palladium catalyst, which is capable of cleaving benzylic C–N bonds, realized facile dearomative reactions with C4 selectivity. Combined with precedented C2- and C3-selective functionalizations of benzyl amine derivatives, the present reaction can provide a new synthetic option for the synthesis of multi-substituted alicyclic compounds as well as aromatic compounds.