N-Heterocyclic carbene catalysis - from simple organic reactions to polymerization of cyclic esters

O. Coulembier; J.-M. Raquez; P. Dubois

Published : 2022-08-23

Vol. 53 No. 4 (2008)

N-Heterocyclic carbene catalysis - from simple organic reactions to polymerization of cyclic esters

O. Coulembier J.-M. Raquez P. Dubois

Abstract

This contribution aims at reporting on very recent advances achieved in controlled ring-opening polymerization of dilactones as promoted by easily accessible N-heterocyclic carbenes (NHCs). Even though carbenes have been known as very unstable species for long, more recently discovered NHC derivatives proved to display higher stability making their handling much easier and allowing their use as efficient catalysts in various organic reactions. Remarkably, these metal-free catalysts display high reactivity in synthesis of aliphatic polyesters such as polylactides and poly(ß-butyrolactone)s all characterized by well-tailored compositions, molecular weight, tacticity, and end-group fidelity while presenting narrow to very narrow molecular weight distribution. Interestingly, novel macromolecular architectures based on such aliphatic polyester building blocks have been made available, e.g. multi-armed star shaped copolyesters, H-shaped copolyesters or macrocyclic polyesters paving the way to new biomedical applications for this family of important biocompatible and biodegradable aliphatic polyesters.

Keywords

karben N-heterocykliczny ; reakcja Stetter'a ; kondensacja benzoinowa ; L,L-laktyd ; ß-lakton ; polimeryzacja z otwarciem pierścienia ; poliestry alifatyczne ; poliestry cykliczne N-heterocyclic carbene ; Stetter reaction ; benzoin condensation ; L,L-lactide ; ß-lactones ; ring opening polymerization ; aliphatic polyesters ; cyclic polyesters

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Coulembier, O., Raquez, J.-M., & Dubois, P. (2022). N-Heterocyclic carbene catalysis - from simple organic reactions to polymerization of cyclic esters. Polimery, 53(4), 255–267. Retrieved from https://ichp.vot.pl/index.php/p/article/view/1307

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O. Coulembier

J.-M. Raquez

P. Dubois philippe.dubois@umh.ac.be

Affiliation
University of Mons-Hainaut, Place du Parc 20, 7000 Mons, Belgium