Synthesis of polyesteramides by palladium-catalyzed carbonylation-polycondensation of aromatic diiodides and amino alcohols

Abstract

Polyesteramides were prepared by palladium-catalyzed carbonylation-polycondensation reaction of aromatic diiodides and amino alcohols. Several polyesteramides with moderate intrinsic viscosity were synthesized in excellent yields using different substrates and characterized. All polymers exhibited characteristic infrared absorption frequencies corresponding to amide and ester carbonyl groups. The effects of reaction parameters such as carbon monoxide pressure, solvent, base, temperature, etc. on the yield and intrinsic viscosity of the polyesteramide obtained were investigated using the carbonylation of 4,4'-diiodobiphenyl and 3-aminopropan-1-ol as a model polymerization reaction. The rate of carbonylation as well as intrinsic viscosity of the resulting polyesteramide increased with increase in the carbon monoxide pressure. Under optimized reaction conditions, the catalyst could be recycled efficiently several times without any loss in activity leading to very high cumulative turnover numbers (>10³) that are almost two orders of magnitude higher than those reported for similar reactions. Polyesteramides were prepared by palladium-catalyzed carbonylation-polycondensation reaction of aromatic diiodides and amino alcohols. The effects of reaction parameters such as carbon monoxide pressure, solvent, base, temperature, etc. on the yield and intrinsic viscosity of the polyesteramide obtained were investigated using the carbonylation of 4,4'-diiodobiphenyl and 3-aminopropan-1-ol as a model polymerization reaction.