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Urea‐ and Thiourea‐Catalyzed Aminolysis of Carbonates
Author(s) -
Blain Marine,
Yau Honman,
JeanGérard Ludivine,
Auvergne Rémi,
Benazet Dominique,
Schreiner Peter R.,
Caillol Sylvain,
Andrioletti Bruno
Publication year - 2016
Publication title -
chemsuschem
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 2.412
H-Index - 157
eISSN - 1864-564X
pISSN - 1864-5631
DOI - 10.1002/cssc.201600778
Subject(s) - aminolysis , thiourea , chemistry , reactivity (psychology) , catalysis , reagent , thio , isocyanate , urea , organic chemistry , carbonate , combinatorial chemistry , ring (chemistry) , polymer chemistry , polyurethane , medicine , alternative medicine , pathology
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 p K a of the (thio)urea and an unqeual substitution pattern is critical for controlling the efficiency of the carbonate opening.