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Organocatalytic Synthesis of Substituted Vinylene Carbonates
Advanced Synthesis & Catalysis ( IF 5.4 ) Pub Date : 2021-09-03 , DOI: 10.1002/adsc.202100870
Killian Onida 1 , Alice Haddleton 2 , Sebastien Norsic 3 , Christophe Boisson 3 , Franck D'Agosto 3 , Nicolas Duguet 1
Affiliation  

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 °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).

中文翻译:

取代碳酸亚乙烯酯的有机催化合成

使用碳酸二苯酯作为羰基源,研究了由安息香和 acyloins 有机催化合成取代的碳酸亚乙烯酯。范围为N- 筛选了杂环卡宾 (NHC) 前体,发现咪唑鎓盐对这种转化最有活性。该反应在 90 °C 下在无溶剂条件下发生。以 20-99% 的分离产率制备了多种取代的碳酸亚乙烯酯(对称和不对称、芳香族或脂肪族),包括一些源自天然产物(24 个例子)。该反应还使用热变形聚乙烯负载的有机催化剂作为可回收和可回收的物质进行开发。使用此类物质有助于后处理,并允许以制备规模合成碳酸亚乙烯酯(5 次运行后 >30 g)。
更新日期:2021-09-03
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