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酯取代的二芳基碘鎓盐能够使萘酚向3,4-苯并香豆素进行区域选择性芳基环化反应。

-ester-substituted diaryliodonium salts enabled regioselective arylocyclization of naphthols toward 3,4-benzocoumarins.

作者信息

Jiang Ke, Pan Cheng, Wang Limin, Wang Hao-Yang, Han Jianwei

机构信息

Key Laboratory for Advanced Materials and Feringa Nobel Prize Scientist Joint Research Center, Department of Fine Chemistry and Institute of Fine Chemicals, School of Chemistry and Molecular Engineering, East China University of Science and Technology, 130 Meilong Road, Shanghai 200237, P. R. China.

National Center for Organic Mass Spectrometry in Shanghai, Shanghai Institute of Organic Chemistry, The Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China.

出版信息

Beilstein J Org Chem. 2024 Apr 18;20:841-851. doi: 10.3762/bjoc.20.76. eCollection 2024.

DOI:10.3762/bjoc.20.76
PMID:38655558
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC11035988/
Abstract

Cyclic annulation involving diaryliodonium salts is an efficient tool for the construction of two or more chemical bonds in a one-pot process. -functionalized diaryliodonium salts have showcased distinct reactivity in the exploration of benzocyclization or arylocyclization. With this strategy of -ester-substituted diaryliodonium salts, herein, we utilized a copper catalyst to activate the C-I bond of diaryliodonium salts in the generation of aryl radicals, thus resulting in an annulation reaction with naphthols and substituted phenols. This approach yielded a diverse array of 3,4-benzocoumarin derivatives bearing various substituents.

摘要

涉及二芳基碘鎓盐的环化反应是一种在一锅法中构建两个或更多化学键的有效工具。-官能化二芳基碘鎓盐在苯并环化或芳基环化的探索中展现出独特的反应活性。利用这种-酯取代二芳基碘鎓盐的策略,在此我们使用铜催化剂在芳基自由基生成过程中活化二芳基碘鎓盐的C-I键,从而与萘酚和取代酚发生环化反应。该方法得到了一系列带有各种取代基的3,4-苯并香豆素衍生物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b842/11035988/83c73c986983/Beilstein_J_Org_Chem-20-841-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b842/11035988/e85674a35dd5/Beilstein_J_Org_Chem-20-841-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b842/11035988/83c73c986983/Beilstein_J_Org_Chem-20-841-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b842/11035988/e85674a35dd5/Beilstein_J_Org_Chem-20-841-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b842/11035988/83c73c986983/Beilstein_J_Org_Chem-20-841-g003.jpg

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本文引用的文献

1
Synthesis of Complex Diarylamines through a Ring-Opening Difunctionalization Strategy.通过开环双官能团化策略合成复杂二芳基胺
Angew Chem Int Ed Engl. 2023 Nov 27;62(48):e202310921. doi: 10.1002/anie.202310921. Epub 2023 Oct 27.
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Diversification of Complex Diaryl Ethers via Diaryliodonium Intramolecular Aryl Rearrangement.通过二芳基碘鎓分子内芳基重排实现复杂二芳基醚的多样化。
J Org Chem. 2023 Sep 15;88(18):13089-13101. doi: 10.1021/acs.joc.3c01293. Epub 2023 Sep 3.
3
Diaryliodonium Salts Enabled Arylation, Arylocyclization, and Aryl-Migration.
二芳基碘鎓盐实现了芳基化、芳基环化和芳基迁移。
Chem Rec. 2023 Oct;23(10):e202300138. doi: 10.1002/tcr.202300138. Epub 2023 May 30.
4
Truce-Smiles Rearrangement of Diaryliodonium Salts in Ionic Liquids.Truce-Smiles 重排反应在离子液体中的二芳基碘鎓盐。
Angew Chem Int Ed Engl. 2023 Jul 10;62(28):e202304897. doi: 10.1002/anie.202304897. Epub 2023 Jun 6.
5
Design, development and applications of copper-catalyzed regioselective (4 + 2) annulations between diaryliodonium salts and alkynes.铜催化二芳基碘鎓盐与炔烃之间区域选择性(4 + 2)环化反应的设计、开发及应用
Commun Chem. 2022 Nov 8;5(1):145. doi: 10.1038/s42004-022-00768-3.
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Recent Progress in Cyclic Aryliodonium Chemistry: Syntheses and Applications.环状芳基碘鎓化学的最新进展:合成与应用
Chem Rev. 2023 Jan 17;123(4):1364-416. doi: 10.1021/acs.chemrev.2c00591.
7
Transition-Metal-Free Difunctionalization of Sulfur Nucleophiles.无过渡金属硫亲核试剂的双官能化反应。
Angew Chem Int Ed Engl. 2023 Feb 13;62(8):e202216296. doi: 10.1002/anie.202216296. Epub 2023 Jan 13.
8
-Nitro-substituted diaryliodonium salts enabled regioselective cyclization of arylcarboxylic acids toward 3,4-naphthocoumarins.硝基亚芳基碘鎓盐促进了芳基羧酸的区域选择性环化反应,生成了 3,4-萘并香豆素。
Org Biomol Chem. 2022 Nov 16;20(44):8628-8632. doi: 10.1039/d2ob01783k.
9
Diaryliodonium(III) salts in one-pot double functionalization of C-I and C-H bonds.碘代二芳基鏻盐在 C-I 和 C-H 键的一锅双官能化反应中的应用。
Org Biomol Chem. 2022 Apr 20;20(16):3231-3248. doi: 10.1039/d1ob02501e.
10
Palladium Catalyzed Regioselective Cyclization of Arylcarboxylic Acids via Radical Intermediates with Diaryliodonium Salts.钯催化通过自由基中间体与二芳基碘鎓盐的芳基羧酸的区域选择性环化反应。
Org Lett. 2021 Nov 19;23(22):8688-8693. doi: 10.1021/acs.orglett.1c03016. Epub 2021 Nov 10.