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Iron-Catalyzed C–H Arylphosphorylation of Quinoxalines
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    Iron-Catalyzed C–H Arylphosphorylation of Quinoxalines
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    • Maoyi Dai
      Maoyi Dai
      Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi 530004, P. R. China
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    • Meilan Xu
      Meilan Xu
      Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi 530004, P. R. China
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    • Xiaoting Gu
      Xiaoting Gu
      Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi 530004, P. R. China
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    • Pengyan Zhang
      Pengyan Zhang
      Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi 530004, P. R. China
    • Yukun Xie
      Yukun Xie
      Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi 530004, P. R. China
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    • Jin Zhuge
      Jin Zhuge
      Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi 530004, P. R. China
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    • Xinting Liang
      Xinting Liang
      Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi 530004, P. R. China
    • Runmin Liao
      Runmin Liao
      Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi 530004, P. R. China
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    • Zongwu Wei
      Zongwu Wei
      School of Resources, Environment and Materials, Guangxi University, Nanning, Guangxi 530004, P. R. China
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    • Zhuan Zhang
      Zhuan Zhang
      Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi 530004, P. R. China
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    • Taoyuan Liang*
      Taoyuan Liang
      Guangxi Colleges and Universities Key Laboratory of Applied Chemistry Technology and Resource Development, School of Chemistry and Chemical Engineering, Guangxi University, Nanning, Guangxi 530004, P. R. China
      *Email: [email protected]
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    Organic Letters

    Cite this: Org. Lett. 2024, 26, 36, 7672–7677
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    https://doi.org/10.1021/acs.orglett.4c02791
    Published September 4, 2024
    Copyright © 2024 American Chemical Society

    Abstract

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    A one-pot strategy for iron-catalyzed C2,3–H arylphosphorylation of electron-deficient quinoxalines with phosphines and aryl compounds is reported. The proposed method features the use of non-noble metal catalysts, the capacity of utilizing multiple aryl compounds as substrates, the simultaneous formation of C–P and C–C bonds in one pot, the simplicity of its operation, the mildness of the reaction conditions, and its compatibility with a wide range of substrates. Moreover, it offers a practical route for direct access to 2-aryl-3-phosphino N-heteroarenes, a class of potential cyclometalated C^N and N^P bidentate ligands that are difficult to prepare with existing C(sp2)–H functionalization methods.

    Copyright © 2024 American Chemical Society

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    Supporting Information

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    The Supporting Information is available free of charge at https://pubs.acs.org/doi/10.1021/acs.orglett.4c02791.

    • Detailed experimental procedures, characterization data, and copies of NMR spectra for all isolated compounds (PDF)

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    CCDC 2343890, 2359697, 2373463, and 2373882 contain the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/data_request/cif, or by emailing [email protected], or by contacting The Cambridge Crystallographic Data Centre, 12 Union Road, Cambridge CB2 1EZ, UK; fax: +44 1223 336033.

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    This article is cited by 3 publications.

    1. Yifeng Liu, Pengyan Zhang, Liangjie Feng, Zhuan Zhang, Taoyuan Liang. Transition-metal-free synthesis of C3,5-difunctionalized oxindole derivatives. Organic Chemistry Frontiers 2025, 12 (8) , 2704-2708. https://doi.org/10.1039/D4QO02428A
    2. Pengyan Zhang, Chenrui Liu, Maoyi Dai, Guangyue Wang, Yurong Huang, Lina Zhang, Cheng Liu, Chengjie He, Xiaoxiang Zhang, Zhuan Zhang, Taoyuan Liang. A one-pot multicomponent tandem reaction for the rapid synthesis of 2-amino-3-benzylindoles. Organic & Biomolecular Chemistry 2025, 23 (14) , 3393-3399. https://doi.org/10.1039/D5OB00187K
    3. Yao Chai, Ya-Ling Tian, Jin-Hong Jia, Xi-Cun Wang, Zheng-Jun Quan. Palladium-catalyzed coupling of aryl sulfonium salts with [TBA][P(SiCl 3 ) 2 ] for the construction of tertiary phosphines. Chemical Communications 2025, 34 https://doi.org/10.1039/D5CC00716J

    Organic Letters

    Cite this: Org. Lett. 2024, 26, 36, 7672–7677
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.4c02791
    Published September 4, 2024
    Copyright © 2024 American Chemical Society

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