Synthesis of polycinnamamide catalyzed by palladium-graphite

Palladium-graphite (Pd-Gr) is useful heterogeneous catalyst for many organic reactions and polycondensations. The catalytic activities of Pd-Gr for the Heck reaction, oxidation, hydrogenation, and nucleophilic substitution of olefin through pi-allyl complex were investigated. The polycondensation of N,N'-(3,4'-oxydiphenylene)bis(acrylamide) and bis(4-iodophenyl) ether catalyzed by Pd-Gr proceeded efficiently in the presence of tributylamine in DMF at 100 degrees C to form polycinnamamide. The polycondensation required longer reaction time compared to the polycondensation catalyzed by palladium acetate. The structure of the resulting polymer was confirmed as trans-polycinnamamide. The resulting polymer was almost white color, which means that it was less contaminated by palladium metal. The removal and recycling of Pd-Gr were much easier than the case of homogeneous catalysts.