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铜促进羧酸与乙烯基磺酰氟（ESF）的共轭加成反应以构建脂肪族磺酰氟。

Copper-Promoted Conjugate Addition of Carboxylic Acids to Ethenesulfonyl Fluoride (ESF) for Constructing Aliphatic Sulfonyl Fluorides.

作者信息

Zhang Xu, Huang Yu-Mei, Qin Hua-Li, Baoguo Zhang, Rakesh K P, Tang Haolin

机构信息

School of Chemistry, Chemical Engineering and Life Science and State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070, China.

Lab of Biorefinery, Shanghai Advanced Research Institute, Chinese Academy of Sciences, No. 99 Haike Road, Pudong, Shanghai 201210, China.

出版信息

ACS Omega. 2021 Sep 27;6(40):25972-25981. doi: 10.1021/acsomega.1c02804. eCollection 2021 Oct 12.

DOI:10.1021/acsomega.1c02804
PMID:34660959
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8515394/
Abstract

A CuO-promoted direct hydrocarboxylation of ethenesulfonyl fluoride (ESF) was developed using carboxylic acid as a nucleophile under mild conditions. A variety of molecules containing both ester group and aliphatic sulfonyl fluoride moiety exhibit great potential in medicinal chemistry and chemical biology. Furthermore, the modification of the known drugs Ibuprofen and Aspirin was also demonstrated.

摘要

在温和条件下，以羧酸为亲核试剂，开发了一种氧化铜促进的乙烯基磺酰氟（ESF）直接氢羧化反应。多种同时含有酯基和脂肪族磺酰氟部分的分子在药物化学和化学生物学中展现出巨大潜力。此外，还展示了对已知药物布洛芬和阿司匹林的修饰。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d25c/8515394/285caaf1bed7/ao1c02804_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d25c/8515394/50e89de22121/ao1c02804_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d25c/8515394/cdabdfd32c8a/ao1c02804_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d25c/8515394/285caaf1bed7/ao1c02804_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d25c/8515394/50e89de22121/ao1c02804_0002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d25c/8515394/cdabdfd32c8a/ao1c02804_0003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/d25c/8515394/285caaf1bed7/ao1c02804_0004.jpg

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本文引用的文献

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J Am Chem Soc. 2020 Dec 16;142(50):20942-20947. doi: 10.1021/jacs.0c10707. Epub 2020 Dec 2.
2
Deoxofluorination of (Hetero)aromatic Acids.脱氟（杂）芳基酸。
J Org Chem. 2020 Mar 6;85(5):3110-3124. doi: 10.1021/acs.joc.9b03011. Epub 2020 Jan 27.
3
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Tetrahedron Lett. 2023 Jun 6;122. doi: 10.1016/j.tetlet.2023.154520. Epub 2023 Apr 28.
Proc Natl Acad Sci U S A. 2019 Sep 17;116(38):18808-18814. doi: 10.1073/pnas.1909972116. Epub 2019 Sep 4.
4
Synthesis of Carboxylic Acids by Palladium-Catalyzed Hydroxycarbonylation.钯催化羟基羰基化合成羧酸
Angew Chem Int Ed Engl. 2019 Oct 1;58(40):14365-14373. doi: 10.1002/anie.201908451. Epub 2019 Aug 28.
5
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6
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9
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