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探索重氮盐形成的流程步骤。

Exploring Flow Procedures for Diazonium Formation.

作者信息

Hu Te, Baxendale Ian R, Baumann Marcus

机构信息

Department of Chemistry, University of Durham, South Road, Durham DH1 3LE, UK.

出版信息

Molecules. 2016 Jul 14;21(7):918. doi: 10.3390/molecules21070918.

DOI:10.3390/molecules21070918
PMID:27428944
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6274498/
Abstract

The synthesis of diazonium salts is historically an important transformation extensively utilized in dye manufacture. However the highly reactive nature of the diazonium functionality has additionally led to the development of many new reactions including several carbon-carbon bond forming processes. It is therefore highly desirable to determine optimum conditions for the formation of diazonium compounds utilizing the latest processing tools such as flow chemistry to take advantage of the increased safety and continuous manufacturing capabilities. Herein we report a series of flow-based procedures to prepare diazonium salts for subsequent in-situ consumption.

摘要

重氮盐的合成在历史上是染料制造中广泛应用的重要转化反应。然而,重氮官能团的高反应活性还催生了许多新反应,包括几种碳-碳键形成过程。因此,利用诸如流动化学等最新加工工具来确定形成重氮化合物的最佳条件,以利用其更高的安全性和连续制造能力,是非常有必要的。在此,我们报告了一系列基于流动的方法,用于制备重氮盐以供后续原位消耗。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e6/6274498/1af77990bb2f/molecules-21-00918-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e6/6274498/698097bbb2dc/molecules-21-00918-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e6/6274498/8c9f4b2b2c27/molecules-21-00918-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e6/6274498/1e1ce4e448e3/molecules-21-00918-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e6/6274498/21585acc572c/molecules-21-00918-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e6/6274498/1af77990bb2f/molecules-21-00918-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e6/6274498/698097bbb2dc/molecules-21-00918-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e6/6274498/8c9f4b2b2c27/molecules-21-00918-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e6/6274498/1e1ce4e448e3/molecules-21-00918-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e6/6274498/21585acc572c/molecules-21-00918-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/55e6/6274498/1af77990bb2f/molecules-21-00918-g009.jpg

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本文引用的文献

1
Flow chemistry as a discovery tool to access sp-sp cross-coupling reactions diazo compounds.流动化学作为一种用于实现sp-sp交叉偶联反应重氮化合物的发现工具。
Chem Sci. 2015 Feb 1;6(2):1120-1125. doi: 10.1039/c4sc03072a. Epub 2014 Nov 7.
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A multistep continuous flow synthesis machine for the preparation of pyrazoles a metal-free amine-redox process.一种用于制备吡唑的多步连续流动合成机器——无金属胺氧化还原过程。
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The synthesis of active pharmaceutical ingredients (APIs) using continuous flow chemistry.
通过重氮中间体的简便分子内[2 + 3]环加成反应形成意外的3,3-二苯基-3-吲唑。
Beilstein J Org Chem. 2019 Jun 19;15:1347-1354. doi: 10.3762/bjoc.15.134. eCollection 2019.
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Flow Hydrodediazoniation of Aromatic Heterocycles.流动氢解芳香杂环化合物。
Molecules. 2019 May 24;24(10):1996. doi: 10.3390/molecules24101996.
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Special Issue "Recent Synthetic Aspects on the Chemistry of Nitro, Nitroso and Amino Compounds".特刊“硝基、亚硝基和氨基化合物化学的最新合成方面”
Molecules. 2016 Dec 23;22(1):9. doi: 10.3390/molecules22010009.
使用连续流动化学合成活性药物成分(原料药)。
Beilstein J Org Chem. 2015 Jul 17;11:1194-219. doi: 10.3762/bjoc.11.134. eCollection 2015.
4
Continuous-flow technology—a tool for the safe manufacturing of active pharmaceutical ingredients.连续流技术——一种用于安全制造活性药物成分的工具。
Angew Chem Int Ed Engl. 2015 Jun 1;54(23):6688-728. doi: 10.1002/anie.201409318. Epub 2015 May 18.
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Amine-terminated monolayers on carbon: preparation, characterization, and coupling reactions.碳表面的胺基端接单层膜:制备、表征及偶联反应
Langmuir. 2015 May 12;31(18):5071-7. doi: 10.1021/acs.langmuir.5b00730. Epub 2015 Apr 29.
6
A three-minute synthesis and purification of ibuprofen: pushing the limits of continuous-flow processing.三分钟内合成并纯化布洛芬:连续流处理的极限挑战。
Angew Chem Int Ed Engl. 2015 Jan 12;54(3):983-7. doi: 10.1002/anie.201409093. Epub 2014 Dec 2.
7
Taming hazardous chemistry in flow: the continuous processing of diazo and diazonium compounds.流动体系中危险化学物质的管控:重氮及重氮鎓化合物的连续加工
Chemistry. 2015 Feb 2;21(6):2298-308. doi: 10.1002/chem.201404348. Epub 2014 Nov 17.
8
Continuous-flow Heck-Matsuda reaction: homogeneous versus heterogeneous palladium catalysts.连续流动赫克-松田反应:均相钯催化剂与非均相钯催化剂
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Chemistry. 2014 May 26;20(22):6603-7. doi: 10.1002/chem.201402092. Epub 2014 Apr 17.
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Genetic incorporation of a 2-naphthol group into proteins for site-specific azo coupling.将 2-萘酚基团遗传整合到蛋白质中以进行位点特异性偶氮偶联。
Bioconjug Chem. 2013 Oct 16;24(10):1645-9. doi: 10.1021/bc400168u. Epub 2013 Oct 2.