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铁介导下由硝基芳烃和酰氯合成芳基酰胺。

Fe-mediated synthesis of -aryl amides from nitroarenes and acyl chlorides.

作者信息

Wu Yundong, Guo Lei, Liu Yuxuan, Xiang Jiannan, Jiang Jun

机构信息

School of Material and Chemical Engineering, Tongren University Tongren 554300 China

College of Chemistry and Chemical Engineering, Hunan University Changsha 410082 China.

出版信息

RSC Adv. 2021 Apr 23;11(25):15290-15295. doi: 10.1039/d0ra10868e. eCollection 2021 Apr 21.

DOI:10.1039/d0ra10868e
PMID:35424062
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8698440/
Abstract

Amides are prevalent in nature and valuable functional compounds in agrochemical, pharmaceutical, and materials industries. In this work, we developed a selective and mild method for the synthesis of -aryl amides. Starting from commercially available nitroarenes and acyl halides, -aryl amides with good yields can be obtained in water. Especially in the process of transformation, Fe dust is the only reductant and additive, and the reaction can be easily performed on a large scale.

摘要

酰胺在自然界中普遍存在，是农用化学品、制药和材料工业中有价值的功能化合物。在这项工作中，我们开发了一种选择性温和的合成β-芳基酰胺的方法。从市售的硝基芳烃和酰卤开始，可在水中以良好的产率获得β-芳基酰胺。特别是在转化过程中，铁粉是唯一的还原剂和添加剂，该反应可以很容易地进行大规模操作。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0b2/8698440/c1df6b8aa37a/d0ra10868e-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0b2/8698440/f455c8f173e0/d0ra10868e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0b2/8698440/e42784f26057/d0ra10868e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0b2/8698440/b721ea62a1ed/d0ra10868e-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0b2/8698440/c1df6b8aa37a/d0ra10868e-s4.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0b2/8698440/f455c8f173e0/d0ra10868e-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0b2/8698440/e42784f26057/d0ra10868e-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0b2/8698440/b721ea62a1ed/d0ra10868e-s3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c0b2/8698440/c1df6b8aa37a/d0ra10868e-s4.jpg

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本文引用的文献

1
Synthesis of N-arylsulfonamides via Fe-promoted reaction of sulfonyl halides with nitroarenes in an aqueous medium.在水相介质中，通过 Fe 促进磺酰卤与硝基芳烃的反应合成 N-芳基磺酰胺。
Org Biomol Chem. 2018 Jul 11;16(27):5016-5020. doi: 10.1039/c8ob01172a.
2
Manganese-Mediated Reductive Transamidation of Tertiary Amides with Nitroarenes.锰介导的叔酰胺与硝基芳烃的还原转酰胺反应。
J Am Chem Soc. 2018 Jun 6;140(22):6789-6792. doi: 10.1021/jacs.8b03739. Epub 2018 May 24.
3
Amide synthesis nickel-catalysed reductive aminocarbonylation of aryl halides with nitroarenes.
酰胺合成：镍催化芳基卤化物与硝基芳烃的还原氨基羰基化反应。
Chem Sci. 2017 Nov 6;9(3):655-659. doi: 10.1039/c7sc03950f. eCollection 2018 Jan 21.
4
Cross-coupling of aromatic esters and amides.芳基酯和酰胺的交叉偶联。
Chem Soc Rev. 2017 Oct 2;46(19):5864-5888. doi: 10.1039/c7cs00182g.
5
Direct amidation of esters with nitroarenes.酯与硝基芳烃的直接酰胺化反应。
Nat Commun. 2017 Mar 27;8:14878. doi: 10.1038/ncomms14878.
6
Erratum: Amine synthesis via iron-catalysed reductive coupling of nitroarenes with alkyl halides.勘误：通过铁催化硝基芳烃与卤代烷的还原偶联合成胺。
Nat Commun. 2016 Dec 6;7:13776. doi: 10.1038/ncomms13776.
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Nonclassical Routes for Amide Bond Formation.非经典酰胺键形成途径。
Chem Rev. 2016 Oct 12;116(19):12029-12122. doi: 10.1021/acs.chemrev.6b00237. Epub 2016 Sep 22.
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