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水相中石墨催化芳基硼酸的官能化反应:无金属合成酚类、苯胺类、硝基芳烃和卤代芳烃。

The graphite-catalyzed -functionalization of arylboronic acids in an aqueous medium: metal-free access to phenols, anilines, nitroarenes, and haloarenes.

作者信息

Dandia Anshu, Sharma Ruchi, Saini Pratibha, Badgoti Ranveer Singh, Rathore Kuldeep S, Parewa Vijay

机构信息

Centre of Advanced Studies, Department of Chemistry, University of Rajasthan Jaipur India

Department of Physics, Arya College of Engineering and IT Jaipur India

出版信息

RSC Adv. 2021 May 19;11(29):18040-18049. doi: 10.1039/d1ra01940f. eCollection 2021 May 13.

DOI:10.1039/d1ra01940f
PMID:35480165
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9033238/
Abstract

An efficient, metal-free, and sustainable strategy has been described for the -functionalization of phenylboronic acids using air as an oxidant in an aqueous medium. A range of carbon materials has been tested as carbocatalysts. To our surprise, graphite was found to be the best catalyst in terms of the turnover frequency. A broad range of valuable substituted aromatic compounds, , phenols, anilines, nitroarenes, and haloarenes, has been prepared the functionalization of the C-B bond into C-N, C-O, and many other C-X bonds. The vital role of the aromatic π-conjugation system of graphite in this protocol has been established and was observed numerous analytic techniques. The heterogeneous nature of graphite facilitates the high recyclability of the carbocatalyst. This effective and easy system provides a multipurpose approach for the production of valuable substituted aromatic compounds without using any metals, ligands, bases, or harsh oxidants.

摘要

已经描述了一种高效、无金属且可持续的策略,用于在水性介质中以空气为氧化剂对苯基硼酸进行官能团化。一系列碳材料已被测试作为碳催化剂。令我们惊讶的是,就周转频率而言,石墨被发现是最佳催化剂。通过将C-B键官能团化为C-N、C-O以及许多其他C-X键,已经制备了多种有价值的取代芳香族化合物,如酚类、苯胺类、硝基芳烃和卤代芳烃。石墨的芳香π共轭体系在该反应中所起的关键作用已通过多种分析技术得以确立并观察到。石墨的非均相性质有利于碳催化剂的高可回收性。这种有效且简便的体系为生产有价值的取代芳香族化合物提供了一种多功能方法,无需使用任何金属、配体、碱或强氧化剂。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/28c4/9033238/ee385ec33caf/d1ra01940f-s5.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/28c4/9033238/ee385ec33caf/d1ra01940f-s5.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/28c4/9033238/538aaff3e6dc/d1ra01940f-s1.jpg
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