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Palladium-Catalyzed ipso-Borylation of Aryl Halides Promoted by Lewis Acid-Mediated Electrophilic Activation of Aryl(halo)palladium(II) Complex

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Download Hi-Res ImageDownload to MS-PowerPointCite This:Org. Lett. 2023, 25, 45, 8173-8177
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    Palladium-Catalyzed ipso-Borylation of Aryl Halides Promoted by Lewis Acid-Mediated Electrophilic Activation of Aryl(halo)palladium(II) Complex
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    • Takashi Niwa*
      Takashi Niwa
      Laboratory for Chemical Biology, RIKEN Center for Biosystems Dynamics Research (BDR), 6-7-3 Minatojima-minamimachi, Chuo-ku, Kobe 650-0047, Japan
      Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan
      Graduate School of Pharmaceutical Sciences, Kyushu University, 3-1-1 Maidashi, Higashi-ku, Fukuoka 812-8582, Japan
      *[email protected]
      More by Takashi Niwa
      Orcidhttps://orcid.org/0000-0002-6209-5362
    • Tadashi Takimoto
      Tadashi Takimoto
      Laboratory for Chemical Biology, RIKEN Center for Biosystems Dynamics Research (BDR), 6-7-3 Minatojima-minamimachi, Chuo-ku, Kobe 650-0047, Japan
      More by Tadashi Takimoto
    • Yuki Sakata
      Yuki Sakata
      Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan
      More by Yuki Sakata
    • Takamitsu Hosoya*
      Takamitsu Hosoya
      Laboratory for Chemical Biology, RIKEN Center for Biosystems Dynamics Research (BDR), 6-7-3 Minatojima-minamimachi, Chuo-ku, Kobe 650-0047, Japan
      Laboratory of Chemical Bioscience, Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University (TMDU), 2-3-10 Kanda-Surugadai, Chiyoda-ku, Tokyo 101-0062, Japan
      *[email protected]
      More by Takamitsu Hosoya
      Orcidhttps://orcid.org/0000-0002-7270-351X
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    Organic Letters

    Cite this: Org. Lett. 2023, 25, 45, 8173–8177
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    https://doi.org/10.1021/acs.orglett.3c03531
    Published November 8, 2023
    Copyright © 2023 American Chemical Society
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    Abstract

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    Palladium-catalyzed ipso-borylation of aryl halides, well-known as Miyaura borylation, is one of the reliable synthetic methods for organoborons. This reaction involves base-mediated nucleophilic activation of diboron that enables transmetalation of an aryl(halo)palladium(II) intermediate with a diboron. As an alternative, herein, we have established Lewis acid-mediated conditions for borylating (pseudo)haloarenes that require no external base. The electrophilic activation of the aryl(halo)palladium(II) intermediate via dehalogenation with Lewis acidic zinc complexes promotes the borylation.

    Copyright © 2023 American Chemical Society

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    This article is cited by 4 publications.

    1. Brittany L. Gay, Lauren A. Prendeville, Ya-Nong Wang, Kami L. Hull. Base-Free Borylation of Aryl Halides Enabled by Zn-Promoted Halide Abstraction. Organic Letters 2024, 26 (49) , 10481-10486. https://doi.org/10.1021/acs.orglett.4c03821
    2. Aishwarya Prakash, Suma Basappa, Bhavya Jeebula, Doddahalli H. Nagaraju, Rajendra S. Dhayal, Shubhankar Kumar Bose. A Simple Nickel Metal–Organic Framework-Catalyzed Borylation of Aryl Chlorides and Bromides. Organic Letters 2024, 26 (13) , 2569-2573. https://doi.org/10.1021/acs.orglett.4c00535
    3. Yu Chen, Ruyi Yuan, Tongtong Zheng, Qingting Guo, Yingming Yao, Li Zhang. Pd-catalyzed deuteration of aryl halides with deuterium oxide. Nature Communications 2025, 16 (1) https://doi.org/10.1038/s41467-025-57855-x
    4. Takashi Niwa, Takamitsu Hosoya. Molecular Design and Synthetic Strategy toward Development of PET Probes. Journal of Synthetic Organic Chemistry, Japan 2024, 82 (5) , 433-449. https://doi.org/10.5059/yukigoseikyokaishi.82.433
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    Organic Letters

    Cite this: Org. Lett. 2023, 25, 45, 8173–8177
    Click to copy citationCitation copied!
    https://doi.org/10.1021/acs.orglett.3c03531
    Published November 8, 2023
    Copyright © 2023 American Chemical Society
    Request reuse permissions

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