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吡啶向芳基二醛的骨架编辑。

Skeletal editing of pyridines to aryldialdehydes.

作者信息

Yan Meixin, Shi Yonglin, Lv Cong, Huang Shunyao, Li Shun, Yang Dexi, Zhao Jiangui, Su Zhishan, Jiang Weidong, Xue Weichao, Xu Jiaqi, Zheng Xueli, Li Ruixiang, Chen Hua, Fu Haiyan

机构信息

Key Laboratory of Green Chemistry & Technology, Ministry of Education, College of Chemistry, Sichuan University, Chengdu, Sichuan, PR China.

College of New Energy Materials and Chemistry, Leshan Normal University, Leshan, Sichuan, PR China.

出版信息

Nat Commun. 2025 Aug 4;16(1):7133. doi: 10.1038/s41467-025-62627-8.

DOI:10.1038/s41467-025-62627-8
PMID:40759905
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12322128/
Abstract

Electron-deficient nitrogen-containing aromatic heterocycles, particularly pyridine derivatives, can be converted into all-carbon aromatic frameworks via the ANRORC (Addition of Nucleophile, Ring-Opening, and Ring-Closing) skeletal editing process, providing a convenient tool for molecular diversification. However, reported methods are mainly limited to nucleophilic modification of ring-opening species. Herein, we report a distinct electrophilic modification method, smoothly converting pyridines into arene-1,3-dialdehydes or naphthalene-1,3-dialdehydes.

摘要

缺电子含氮芳香杂环,特别是吡啶衍生物,可通过亲核试剂加成、开环和闭环(ANRORC)骨架编辑过程转化为全碳芳香骨架,为分子多样化提供了一种便捷工具。然而,已报道的方法主要限于开环物种的亲核修饰。在此,我们报道了一种独特的亲电修饰方法,可将吡啶顺利转化为芳烃-1,3-二醛或萘-1,3-二醛。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07b1/12322128/fe899054e32d/41467_2025_62627_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07b1/12322128/807e426df312/41467_2025_62627_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07b1/12322128/0958d2827a00/41467_2025_62627_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07b1/12322128/c59e18f0fa54/41467_2025_62627_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07b1/12322128/a47c5951d406/41467_2025_62627_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07b1/12322128/fe899054e32d/41467_2025_62627_Fig5_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07b1/12322128/807e426df312/41467_2025_62627_Fig1_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07b1/12322128/0958d2827a00/41467_2025_62627_Fig2_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07b1/12322128/c59e18f0fa54/41467_2025_62627_Fig3_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07b1/12322128/a47c5951d406/41467_2025_62627_Fig4_HTML.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/07b1/12322128/fe899054e32d/41467_2025_62627_Fig5_HTML.jpg

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本文引用的文献

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Copper-Catalyzed Enantioselective Skeletal Editing through a Formal Nitrogen Insertion into Indoles to Synthesize Atropisomeric Aminoaryl Quinoxalines.通过将氮正式插入吲哚中以合成阻转异构氨基芳基喹喔啉的铜催化对映选择性骨架编辑。
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Asymmetric dearomative single-atom skeletal editing of indoles and pyrroles.吲哚和吡咯的不对称去芳香化单原子骨架编辑
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Nitrogen-to-functionalized carbon atom transmutation of pyridine.
吡啶的氮到官能化碳原子的嬗变
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4
C3 Selective chalcogenation and fluorination of pyridine using classic Zincke imine intermediates.使用经典的津克(Zincke)亚胺中间体对吡啶进行C3选择性硫属化和氟化反应。
Nat Commun. 2024 Aug 28;15(1):7420. doi: 10.1038/s41467-024-51452-0.
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Pyridine-based strategies towards nitrogen isotope exchange and multiple isotope incorporation.基于吡啶的氮同位素交换和多同位素掺入策略。
Nat Commun. 2024 Jul 18;15(1):6063. doi: 10.1038/s41467-024-50139-w.
6
Regioselective Pyridine to Benzene Edit Inspired by Water-Displacement.受水置换启发的区域选择性吡啶到苯的编辑
J Am Chem Soc. 2024 Jul 24;146(29):19660-19666. doi: 10.1021/jacs.4c05999. Epub 2024 Jul 12.
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Radical -C-H Halogenation of Azines via -Benzyl Activation Strategy.通过苄基活化策略实现嗪类化合物的自由基-C-H卤化反应
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9
N to N Isotopic Exchange of Nitrogen Heteroaromatics through Skeletal Editing.通过骨架编辑实现氮杂芳烃的N到N同位素交换。
J Am Chem Soc. 2024 Feb 7;146(5):2950-2958. doi: 10.1021/jacs.3c11515. Epub 2024 Jan 29.
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Skeletal editing of pyridines through atom-pair swap from CN to CC.通过从 CN 到 CC 的原子对交换对吡啶进行骨架编辑。
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