Approach toward the Understanding of Coupling Mechanism for EDC Reagent in Solvent-Free Mechanosynthesis,Organic Letters

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Approach toward the Understanding of Coupling Mechanism for EDC Reagent in Solvent-Free Mechanosynthesis
Organic Letters ( IF 4.9 ) Pub Date : 2017-09-22 00:00:00 , DOI: 10.1021/acs.orglett.7b02637
Aneta Wróblewska ₁ , Piotr Paluch ₁ , Ewelina Wielgus ₁ , Grzegorz Bujacz ₂ , Marta K. Dudek ₁ , Marek J. Potrzebowski ₁

Affiliation

A unique approach in mechanosynthesis, joining solid-state NMR spectroscopy, X-ray crystallography, and theoretical calculations, is employed for the first time to study the mechanism of the formation of the C–N amide bond using EDC·HCl as a coupling reagent. It has been proved that EDC·HCl, which in the crystal lattice exists exclusively in the cyclic form (X-ray data), easily undergoes transformation to a pseudocyclic stable intermediate in reaction with carboxylic acid forming a low-melt phase (differential scanning calorimetry, solid-state NMR). The obtained intermediate is reactive and can be further used for synthesis of amides in reaction with appropriate amines.

中文翻译：

理解无溶剂机械合成中EDC试剂偶联机理的方法

首次采用独特的机械合成方法，结合固态NMR光谱，X射线晶体学和理论计算，以EDC·HCl作为偶联剂研究了C–N酰胺键的形成机理。。业已证明，在晶格中仅以环状形式存在的EDC·HCl（X射线数据）在与羧酸反应形成低熔点相时，很容易转变为假环稳定中间体（差示扫描量热法），固态NMR）。所获得的中间体是反应性的，并且可以在与适当的胺反应中进一步用于酰胺的合成。

更新日期：2017-09-22

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