Accelerated Amidation of a Glycine Propargyl Ester on a Polymer and the Two-Way Use of One-Pot Double Postpolymerization Modification with Click Chemistry

Abstract

Abstract The glycine propargyl (GP) ester moiety, as a newly activated ester, is a candidate for amidation in modification reactions and can be combined with click chemistry. Here, the amidation of GP esters on a polymer side chain was investigated using various amino-group-containing compounds. The amidation on the GP ester proceeded well when n-alkyl, cycloalkyl, and aromatic-group-containing primary amines were used without a catalyst under neutral conditions. Hydrophilic amines containing hydroxy and carboxy groups provided no amidation products. The amidation on the polymer was accelerated by the neighboring group effect on the polymer side chain. One-pot double postpolymerization modification was achieved using a GP ester-bearing polymer by combining amidation with the Huisgen cycloaddition.