Pd(O)-Catalyzed allylations of 4(5)-nitroimidazole, 1, 2-methyl-4(5)-nitroimidazole, 2, 4(5)-bromoimidazole, 7, 4(5)-methoxyimidazole, 10, 5(6)-nitrobenzimidazole, 16a, 5(6)-methylbenzimidazole, 16b, benzotriazole, 19, and 5(6)-methylbenzotriazole, 22, were studied under several reaction conditions. Nitroimidazoles 1 and 2 were regioselectively allylated under thermodynamic control, leading to 1-allyl-4-nitro derivatives.