Urea- and Thiourea-Catalyzed Aminolysis of Carbonates

被引：71

作者：

Blain, Marine ^{[1
,2
]}

Yau, Honman ^{[3
]}

Jean-Gerard, Ludivine ^{[1
]}

Auvergne, Remi ^{[2
]}

Benazet, Dominique ^{[4
]}

Schreiner, Peter R. ^{[3
]}

Caillol, Sylvain ^{[2
]}

Andrioletti, Bruno ^{[1
]}

机构：

[1] Univ Lyon 1, ICBMS, CNRS, UMR 5246,CPE, Campus LyonTech Doua Bat Curien, F-69622 Villeurbanne, France

[2] UM, ENSCM, CNRS, Ingn Architecture Macromol,UMR 5253,Inst Charles, 8 Rue Ecole Normale, F-34296 Montpellier, France

[3] Univ Giessen, Inst Organ Chem, Heinrich Buff Ring 17, D-35392 Giessen, Germany

[4] Juxta, 5 Rue Jalesie,BP 71039, F-25401 Audincourt, France

来源：

CHEMSUSCHEM | 2016年 / 9卷 / 16期

关键词：

aminolysis; catalysis; polyurethanes; pk(a); reactivity; 5-MEMBERED CYCLIC CARBONATE; DIELS-ALDER REACTIONS; EQUILIBRIUM ACIDITIES; MODEL REACTION; AMINES; POLYURETHANES; ISOCYANATE; POLYHYDROXYURETHANES; REACTIVITY; PRECURSORS;

D O I：

10.1002/cssc.201600778

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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 pK(a) of the (thio)urea and an unqeual substitution pattern is critical for controlling the efficiency of the carbonate opening.

引用

页码：2269 / 2272

页数：4

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