Concurrent Oxidation of Alcohols and the Passerini Three‐Component Polymerization for the Synthesis of Functional Poly(ester amide)s

Abstract

A new polymerization method based on the Passerini three‐component reaction of a dicarboxylic acid, an alcohol, and a diisocyanide in the presence of an oxidant is reported. This polymerization involves the concurrent oxidation of alcohols by o‐iodoxybenzoic acid (IBX) and the Passerini three‐component polymerization. The kinetics of the alcohol oxidation and the Passerini reaction are investigated, and the results indicate that the cascade process can occur efficiently. The reaction conditions are optimized, and various functional alcohols are examined to get insight into the applicability of the method. Based on the optimized conditions, a variety of functional poly(ester amide)s are prepared in a one‐pot fashion via using 1,6‐diisocyanohexane, 1,6‐hexanedioic acid, different functional alcohols, and iodoxybenzoic acid. The introduction of functional pendant groups, especially alkynyl, alkenyl and epoxy groups, to the final poly(ester amide)s, provides an efficient way for further modification of the polymers. image