Phenols and Tertiary Amines: An Amazingly Simple Hydrogen-Bonding Organocatalytic System Promoting Ring Opening Polymerization

Coralie Thomas (1, 2) , Frédéric Peruch (2, 3) , Alain Deffieux (2, 3) , Anne Milet (4) , Jean-Pierre Desvergne (1) , Brigitte Bibal (1)

1 ISM - Institut des Sciences Moléculaires
2 LCPO - Laboratoire de Chimie des Polymères Organiques
3 Team 1 LCPO : Polymerization Catalyses & Engineering
4 DCM - CT - Département de Chimie Moléculaire - Chimie Théorique

A simple and easily available organocatalytic system was developed for the polymerization of lactide. In partnership with tertiary amines, phenol derivatives were demonstrated to be excellent single H-bonding catalysts with high conversion within 24 h. In particular, ortho-, meta- and meta,meta'-trifluoromethylphenols revealed an amazing capacity for triggering the controlled ring opening polymerization (ROP) of lactide, through a fitted hydrogen-bond with the monomer.

Mots clés: phenols; organic catalysis; polymerization; polylactide; hydrogen bonds

Domaines: Polymères

Coralie Thomas, Frédéric Peruch, Alain Deffieux, Anne Milet, Jean-Pierre Desvergne, et al.. Phenols and Tertiary Amines: An Amazingly Simple Hydrogen-Bonding Organocatalytic System Promoting Ring Opening Polymerization. Advanced Synthesis and Catalysis, 2011, 353 (7), pp.1049-1054. ⟨10.1002/adsc.201100013⟩. ⟨hal-00947127⟩