CHAPTER 17. Ionic Liquid Effect in Catalysed Multicomponent Reactions

B. A. Neto, Haline G. O. Alvim, A. Lapis
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Abstract

In this book chapter the effects produced in using ionic liquids over multicomponent reactions are presented and discussed. Ionic liquids may be used as reaction media (solvents) or as catalysts for several multicomponent reactions. It is observed that many multicomponent reactions characteristically proceed through charged intermediates, thereby rendering them as desirable features to interact with cations and/or anions of ionic liquids. These interactions are mostly ruled by Coulombic attraction/stabilisation between the charged intermediates and the ionic liquid ions. These Coulombic interactions give rise to new ion pairs and larger supramolecular aggregates (higher ion clusters). Additional interactions such as hydrogen bonds and van der Waals forces also play a role in the formation, directionality (entropic drivers) and stabilisation of these ion pairs (and larger supramolecular clusters) between the charged intermediates and the ionic liquid ions; an effect typically noted for imidazolium derivatives. Understanding the multicomponent reaction mechanism in this context is essential in aiming at predicting a positive ionic liquid effect. Many multicomponent reactions have proven to be capable of undergoing two or more competitive reaction mechanisms, but usually the final multicomponent reaction adduct is the same regardless of the reaction pathway. Ionic liquids may also contribute to tune the reaction through one specific mechanism. As we intend to show herein, the combination of multicomponent reactions and ionic liquids typically returns excellent results and produces many achievements, although both are a huge challenge to understand and to predict their effects over multicomponent reactions.
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第十七章。催化多组分反应中的离子液体效应
在这本书的章节中,离子液体在多组分反应中产生的影响被提出和讨论。离子液体可用作反应介质(溶剂)或多种多组分反应的催化剂。可以观察到,许多多组分反应的特征是通过带电中间体进行,从而使它们成为与离子液体的阳离子和/或阴离子相互作用的理想特征。这些相互作用主要是带电中间体和离子液体离子之间的库仑吸引/稳定作用。这些库仑相互作用产生新的离子对和更大的超分子聚集体(更高的离子簇)。额外的相互作用,如氢键和范德华力,也在带电中间体和离子液体离子之间的这些离子对(以及更大的超分子簇)的形成、方向性(熵驱动因素)和稳定性中发挥作用;咪唑类衍生物的典型效应。在这种情况下,了解多组分反应机理对于预测正离子液体效应至关重要。许多多组分反应已被证明能够经历两种或两种以上的竞争性反应机制,但通常最终的多组分反应加合物是相同的,而不管反应途径如何。离子液体也可能通过一种特定的机制来调节反应。正如我们打算在这里展示的那样,多组分反应和离子液体的结合通常会产生出色的结果并产生许多成就,尽管理解和预测它们对多组分反应的影响都是一个巨大的挑战。
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