Organocatalytic Synthesis of Substituted Vinylene Carbonates

被引：7

作者：

Onida, Killian ^{[1
]}

Haddleton, Alice J. ^{[2
]}

Norsic, Sebastien ^{[2
]}

Boisson, Christophe ^{[2
]}

D'Agosto, Franck ^{[2
]}

Duguet, Nicolas ^{[1
]}

机构：

[1] Univ Claude Bernard Lyon 1, Univ Lyon, CNRS,ICBMS,UMR 5246,Team CAtalyse SYnth & Environ, INSA Lyon,CPE Lyon,Inst Chim & Biochim Mol & Supr, Batiment Lederer,1 Rue Victor Grignard, F-69622 Villeurbanne, France

[2] Univ Lyon 1, Univ Lyon, CPE Lyon, CNRS UMR 5128,Lab Catalysis Polymerizat Proc & Ma, Bat 308F,43 Bd 11 Novembre 1918, F-69616 Villeurbanne, France

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2021年 / 363卷 / 22期

关键词：

Vinylene carbonates; Benzoin; Diphenyl carbonate; Organocatalysis; Thermomorphic polyethylene; N-HETEROCYCLIC CARBENES; ALKYLIDENE CYCLIC CARBONATES; NON-ISOCYANATE POLYURETHANES; EFFICIENT SYNTHESIS; CATALYZED SYNTHESIS; CYCLOADDITION; CO2; DERIVATIVES; AMINOLYSIS; EPOXIDES;

D O I：

10.1002/adsc.202100870

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

The organocatalytic synthesis of substituted vinylene carbonates from benzoins and acyloins was studied using diphenyl carbonate as a carbonyl source. A range of N-Heterocyclic Carbene (NHC) precursors were screened and it was found that imidazolium salts were the most active for this transformation. The reaction occurs at 90 degrees C under solvent-free conditions. A wide range of substituted vinylene carbonates (symmetrical and unsymmetrical, aromatic or aliphatic), including some derived from natural products, were prepared with 20-99% isolated yields (24 examples). The reaction was also developed using thermomorphic polyethylene-supported organocatalysts as recoverable and recyclable species. The use of such species facilitates the workup and allows the synthesis of vinylene carbonates on the preparative scale (>30 g after 5 runs).

引用

页码：5129 / 5137

页数：9

共 92 条

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