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首页> 外文期刊>Chemistry: A European journal >A Simple and Efficient Catalytic System for N-Arylation of Imidazoles in Water
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A Simple and Efficient Catalytic System for N-Arylation of Imidazoles in Water

机译：一种简单高效的咪唑在水中N-芳基化的催化体系

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摘要

N-Aryl imidazoles are key structural motifs in a wide range of agrochemicals, pharmaceuticals, and biologically active compounds[1] and have been exploited as important precursors of versatile N-heterocyclic carbenes,[2] a powerful class of ligands for transition-metal catalysis[3] or room-temperature ionic liquids.[4] A traditional method of introducing this functionality is nucleophilic aromatic substitution of imidazole with activated aryl halides (SNAr reactions) or classic Ullmann-type coupling reactions.[5] However, these well-known methods suffer from several drawbacks, such as high reaction temperature, stiochiometric amounts of metal reagents, and low functional-group tolerance, which has limited their applications. Recently, Buchwald et al.[6] and Taillefer et al.[7] found several N- and O-based ligands could greatly facilitate the copper-catalyzed path for the N-arylation of imidazoles. After the discovery of these ligands, ACHTUNGTRENUNGinterest in this field has increased spectacularly in the last few years[8] and resulted in the golden age of copper-catalyzed Ullmann-type coupling reactions. While many important results have been achieved via this methodology, it is worth noting that these protocols are generally operated in volatile organic solvents with transitionmetal ions. From the standpoint of greenchemistry, the development of more environmentally benign reaction media,such as water, in place of organic solvents would be desirable.[9] Henceforth, as part of our endeavors toward the development of environmentally friendly protocols, efforts were directed towards performing the N-arylation reaction by using water as the sole reaction medium.
机译：N-芳基咪唑是广泛的农用化学品，药物和生物活性化合物的关键结构基序[1]，已被用作多功能N-杂环卡宾的重要前体，[2]一类功能强大的过渡金属配体催化[3]或室温离子液体。[4]引入该功能的传统方法是用活化的芳基卤化物（SNAr反应）或经典的Ullmann型偶联反应对咪唑进行亲核芳香取代。[5]但是，这些众所周知的方法具有一些缺点，例如反应温度高，金属试剂的化学计量量和官能团耐受性低，这限制了它们的应用。最近，Buchwald等人[6]和Taillefer等人[7]发现几种基于N和O的配体可以极大地促进铜催化的咪唑N-芳基化路径。在发现了这些配体之后，近几年来ACHTUNGTRENUNG在该领域的兴趣急剧增加[8]，并导致了铜催化的Ullmann型偶联反应的黄金时代。尽管通过这种方法已经获得了许多重要的结果，但值得注意的是，这些协议通常是在具有过渡金属离子的挥发性有机溶剂中进行的。从绿色化学的角度来看，人们希望开发一种对环境更友好的反应介质，例如水来代替有机溶剂。[9]今后，作为我们开发环境友好方案的努力的一部分，致力于通过使用水作为唯一的反应介质来进行N-芳基化反应。

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