Ambident Reactivity of Imidazolium Cations as Evidence of the Dynamic Nature of N-Heterocyclic Carbene-Mediated Organocatalysis.,Chemistry - A European Journal

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Ambident Reactivity of Imidazolium Cations as Evidence of the Dynamic Nature of N-Heterocyclic Carbene-Mediated Organocatalysis.
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2020-03-30 , DOI: 10.1002/chem.201905704
Konstantin I Galkin ₁ , Bogdan Ya Karlinskii ₁ , Alexander Yu Kostyukovich ₁ , Evgeniy G Gordeev ₁ , Valentine P Ananikov ₁

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This work reveals ambident nucleophilic reactivity of imidazolium cations towards carbonyl compounds at the C2 or C4 carbene centers depending on the steric properties of the substrates and reaction conditions. Such an adaptive behavior indicates the dynamic nature of organocatalysis proceeding via a covalent interaction of imidazolium carbenes with carbonyl substrates and can be explained by generation of the H‐bonded ditopic carbanionic carbenes.

中文翻译：

咪唑鎓阳离子的环境反应性，作为N-杂环卡宾介导的有机催化动力学性质的证据。

这项工作揭示了咪唑鎓阳离子对C2或C4卡宾中心的羰基化合物的亲核亲核反应性，具体取决于底物的空间性质和反应条件。这种适应性行为表明有机催化通过咪唑鎓碳氮烷与羰基底物的共价相互作用而进行的动力学性质，并且可以通过生成H键合的对位碳酰碳氮烷来解释。

更新日期：2020-03-30

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