Catalyst- and Initiator-Free Radical Addition under Mild Conditions: A Macromolecular Conjugation Tool

Laurent Autissier (1) , Kamel Mabrouk (1) , Christophe Chendo (2) , Yohann Guillaneuf (1) , Marion Rollet (1) , Laurence Charles (1) , Didier Gigmes (1) , Thomas Trimaille (1)

1 ICR - Institut de Chimie Radicalaire
2 FSCM - Fédération des Sciences Chimiques de Marseille

A catalyst/initiator-free radical addition reaction performed under mild conditions (water, 30 degrees C) with high yields is reported for the first time. This reaction implies simple pH-mediated alkoxyamine dissociation followed by addition onto olefinic substrates. The versatility and relevance of this selective reaction for macromolecular conjugation and engineering are shown through the syntheses of block copolymers, as well as hydrogels containing insitu-loaded proteins, which could retain biological activity. This contrasts with standard thermal radical conditions that lead to complete protein inactivation.

Mots clés: access; alkoxyamines; block copolymers; click chemistry; copolymers; hydrogels; olefins; polymerization; powerful; radical addition; water solvent

Domaines: Chimie

Laurent Autissier, Kamel Mabrouk, Christophe Chendo, Yohann Guillaneuf, Marion Rollet, et al.. Catalyst- and Initiator-Free Radical Addition under Mild Conditions: A Macromolecular Conjugation Tool. Chemistry - A European Journal, 2018, 24 (15), pp.3699--3702. ⟨10.1002/chem.201800035⟩. ⟨hal-02091848⟩