葡萄糖吡喃苷取代咪唑基手性离子液体用于pd催化芳基硼酸在水中的均偶联

IF 16.4 1区化学 Q1 CHEMISTRY, MULTIDISCIPLINARY Accounts of Chemical Research Pub Date : 2020-01-01 DOI:10.1080/07328303.2020.1788573

Zhonggao Zhou , Jing Li , Yue Wu , Yangyang Yuan , Lingfang Kong , Jun Xue , Zhiqiang Huang

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引用次数: 6

摘要

手性离子液体(CILs)是一种应用广泛的溶剂和材料，具有突出的性能。碳水化合物衍生的咪唑基CILs是一种独特的CILs类型，具有天然手性池中的多个手性中心。本文合成了一系列吡喃葡萄糖苷取代咪唑基CILs (Glu-imi-CILs)，并对其作为pd催化芳基硼酸在水中的均偶联反应的配体进行了评价。葡萄糖吡喃苷取代基有助于提高催化剂的催化活性。此外，具有游离羟基的Glu-imi-CIL被发现是最有效的配体。用这种方法从芳基硼酸中合成了一系列对称的联芳基化合物(13个例子)，分离收率高(85 ~ 99%)。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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Glucopyranoside-substituted imidazolium-based chiral ionic liquids for Pd-catalyzed homo-coupling of arylboronic acids in water

Chiral ionic liquids (CILs) are widely used solvents and materials with prominent properties. Carbohydrate-derived imidazolium-based CILs represent a distinctive type of CILs possessing multiple chiral centers from natural chiral pool. Herein, a series of glucopyranoside-substituted imidazolium-based CILs (Glu-imi-CILs) were synthesized and evaluated as ligands for Pd-catalyzed homo-coupling reactions of arylboronic acids in water. The glucopyranoside substituent was instrumental for improving the catalytic activity of the resulting catalysts. Moreover, a Glu-imi-CIL with a free hydroxyl group for additional coordination was found to be the most efficient ligand. A series of symmetric biaryl compounds (13 examples) were synthesized from arylboronic acids by this method in high isolated yields (85−99%).

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来源期刊

Accounts of Chemical Research 化学-化学综合

CiteScore

31.40

自引率

1.10%

发文量

312

审稿时长

2 months

期刊介绍： Accounts of Chemical Research presents short, concise and critical articles offering easy-to-read overviews of basic research and applications in all areas of chemistry and biochemistry. These short reviews focus on research from the author’s own laboratory and are designed to teach the reader about a research project. In addition, Accounts of Chemical Research publishes commentaries that give an informed opinion on a current research problem. Special Issues online are devoted to a single topic of unusual activity and significance. Accounts of Chemical Research replaces the traditional article abstract with an article "Conspectus." These entries synopsize the research affording the reader a closer look at the content and significance of an article. Through this provision of a more detailed description of the article contents, the Conspectus enhances the article's discoverability by search engines and the exposure for the research.