Iron-Assisted and Cu-Mediated Direct Aminocarbonylation of Nitroarene with Boronic Acid

IF 3.6 2区 化学 Q1 CHEMISTRY, ORGANIC Journal of Organic Chemistry Pub Date : 2024-12-24 DOI:10.1021/acs.joc.4c02232
Deepak Sharma, Charu Sharma, Sangeeta Kumari, Raj K. Joshi
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Abstract

Herein, we have established the formation of diaryl amide by aminocarbonylation of nitrobenzene with boronic acids. The method works in the catalytic presence of economical and commercially available CuI salt, which was significantly promoted by the Fe3Se2(CO)9 cluster. Mo(CO)6 serves as a source of CO, and it also acts as a reductant with a combination of iron cluster. Moreover, all the reaction worked under the ligand-free system and produced the desired diaryl amide in a significant time of 10 h. Water, a green solvent, was used as a source of hydrogen for the reduction of nitrobenzene to aniline. The method depicts a suitable functional group tolerance and produces a wide range of substrates in good to excellent amounts. To the best of our knowledge, this is the first report for the direct aminocarbonylation mediated by highly economical CuI. Moreover, water as a source of hydrogen for the reduction of nitroarene is always appreciated.

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铁辅助和铜介导的硝基芳烃与硼酸直接氨基羰基化反应
在这里,我们已经建立了硝基苯与硼酸氨基羰基化形成二芳基酰胺。该方法在经济和市售的崔盐存在下有效,Fe3Se2(CO)9簇显著促进了催化反应。Mo(CO)6作为CO的来源,同时也作为还原剂与铁簇结合。此外,所有反应均在无配体体系下进行,并在10 h的显著时间内生成所需的二芳基酰胺。水作为一种绿色溶剂,作为氢源将硝基苯还原为苯胺。该方法描述了合适的官能团耐受性,并生产了大量的底物。据我们所知,这是首次报道由高度经济的CuI介导的直接氨基羰基化反应。此外,水作为还原硝基芳烃的氢源一直受到赞赏。
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来源期刊
Journal of Organic Chemistry
Journal of Organic Chemistry 化学-有机化学
CiteScore
6.20
自引率
11.10%
发文量
1467
审稿时长
2 months
期刊介绍: Journal of Organic Chemistry welcomes original contributions of fundamental research in all branches of the theory and practice of organic chemistry. In selecting manuscripts for publication, the editors place emphasis on the quality and novelty of the work, as well as the breadth of interest to the organic chemistry community.
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