Improved Protocols for the Synthesis of Precursors of Thiazol-2-ylidene N-Heterocyclic Carbenes,Synlett

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Improved Protocols for the Synthesis of Precursors of Thiazol-2-ylidene N-Heterocyclic Carbenes
Synlett ( IF 1.7 ) Pub Date : 2024-03-28 , DOI: 10.1055/a-2284-4798
Eder Tomás-Mendivil ₁ , David Martin ₁ , Ludivine Delfau ₁ , Jacques Pecaut ₁

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We report improved protocols for the synthesis of thiazolium precatalysts from primary amines, carbon disulfide, and α-halo ketones. For N-alkyl-substituted derivatives, yields of the corresponding thiazolethiones can be dramatically improved by isolating the intermediate dithiocarbamates. In most cases, meta-chloroperbenzoic acid can advantageously replace H₂O₂ in acetic acid for the oxidation of thiazolethiones into thiazoliums. This approach was applied to the synthesis of a thiazolium featuring a 2-adamantyl N-substituent, the corresponding persistent carbene, and its dimer.

中文翻译：

噻唑-2-亚基 N-杂环卡宾前体合成的改进方案

我们报告了从伯胺、二硫化碳和 α-卤代酮合成噻唑鎓预催化剂的改进方案。对于N-烷基取代的衍生物，通过分离中间体二硫代氨基甲酸酯可以显着提高相应噻唑硫酮的产率。在大多数情况下，间氯过苯甲酸可以有利地代替乙酸中的H ₂ O ₂以将噻唑硫酮氧化成噻唑鎓。该方法应用于合成具有 2-金刚烷基N取代基的噻唑鎓、相应的持久卡宾及其二聚体。

更新日期：2024-03-29

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