title: Urea- and Thiourea-Catalyzed Aminolysis of Carbonates.
abstract: The aminolysis of (poly)carbonates by (poly)amines provides access to non-isocyanate polyurethanes (NIPUs) that are toxic-reagent-free analogues of polyurethanes (PUs). Owing to their low reactivity, the ring opening of cyclic carbonates requires the use of a catalyst. Herein, we report that the more available and cheaper ureas could advantageously be used for catalyzing the formation of NIPUs at the expense of the thiourea analogues. In addition, we demonstrate a medium-range pKa of the (thio)urea and an unqeual substitution pattern is critical for controlling the efficiency of the carbonate opening.
authors.affiliation: Université de Lyon, Université Claude Bernard-Lyon 1, ICBMS-UMR CNRS 5246 Campus LyonTech la Doua - Bât. Curien/CPE, 43 Boulevard du 11 Novembre 1918, 69622, Villeurbanne Cedex, France.|Ingénierie Architecture Macromoléculaire, Institut Charles Gerhardt UMR 5253 - CNRS, UM, ENSCM, 8, Rue Ecole Normale, 34296, Montpellier, France.
authors.forename: Marine
authors.initials: M
authors.lastname: Blain
authors.affiliation: Institute of Organic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 17, 35392, Giessen, Germany.
authors.forename: Honman
authors.initials: H
authors.lastname: Yau
authors.affiliation: Université de Lyon, Université Claude Bernard-Lyon 1, ICBMS-UMR CNRS 5246 Campus LyonTech la Doua - Bât. Curien/CPE, 43 Boulevard du 11 Novembre 1918, 69622, Villeurbanne Cedex, France.
authors.forename: Ludivine
authors.initials: L
authors.lastname: Jean-Gérard
authors.affiliation: Ingénierie Architecture Macromoléculaire, Institut Charles Gerhardt UMR 5253 - CNRS, UM, ENSCM, 8, Rue Ecole Normale, 34296, Montpellier, France.
authors.forename: Rémi
authors.initials: R
authors.lastname: Auvergne
authors.affiliation: Juxta, 5 rue de la Jalesie, BP 71039, 25401, Audincourt cedex, France.
authors.forename: Dominique
authors.initials: D
authors.lastname: Benazet
authors.affiliation: Institute of Organic Chemistry, Justus-Liebig University, Heinrich-Buff-Ring 17, 35392, Giessen, Germany.
authors.forename: Peter R
authors.identifier: 0000-0002-3608-5515
authors.initials: PR
authors.lastname: Schreiner
authors.affiliation: Ingénierie Architecture Macromoléculaire, Institut Charles Gerhardt UMR 5253 - CNRS, UM, ENSCM, 8, Rue Ecole Normale, 34296, Montpellier, France. Sylvain.Caillol@enscm.fr.
authors.forename: Sylvain
authors.initials: S
authors.lastname: Caillol
authors.affiliation: Université de Lyon, Université Claude Bernard-Lyon 1, ICBMS-UMR CNRS 5246 Campus LyonTech la Doua - Bât. Curien/CPE, 43 Boulevard du 11 Novembre 1918, 69622, Villeurbanne Cedex, France. bruno.andrioletti@univ-lyon1.fr.
authors.forename: Bruno
authors.initials: B
authors.lastname: Andrioletti
mesh_terms: D002254:Carbonates / Q000737:chemistry*; D002384:Catalysis; D003514:Cyclohexylamines / Q000737:chemistry; D013890:Thiourea / Q000737:chemistry*
chemical_list: D002254:Carbonates; D003514:Cyclohexylamines; D013890:Thiourea
keywords: aminolysis; catalysis; pka; polyurethanes; reactivity