IDEAS home Printed from https://ideas.repec.org/a/nat/nature/v575y2019i7782d10.1038_s41586-019-1640-2.html
   My bibliography  Save this article

Metal-free directed sp2-C–H borylation

Author

Listed:
  • Jiahang Lv

    (Nanjing University
    Yangzhou University)

  • Xiangyang Chen

    (University of California, Los Angeles)

  • Xiao-Song Xue

    (University of California, Los Angeles
    Nankai University)

  • Binlin Zhao

    (Nanjing University)

  • Yong Liang

    (Nanjing University)

  • Minyan Wang

    (Nanjing University)

  • Liqun Jin

    (Zhejiang University of Technology)

  • Yu Yuan

    (Yangzhou University)

  • Ying Han

    (Yangzhou University)

  • Yue Zhao

    (Nanjing University)

  • Yi Lu

    (Nanjing University)

  • Jing Zhao

    (Nanjing University)

  • Wei-Yin Sun

    (Nanjing University)

  • Kendall. N. Houk

    (University of California, Los Angeles)

  • Zhuangzhi Shi

    (Nanjing University
    Yangzhou University
    Nankai University)

Abstract

Organoboron reagents are important synthetic intermediates that have a key role in the construction of natural products, pharmaceuticals and organic materials1. The discovery of simpler, milder and more efficient approaches to organoborons can open additional routes to diverse substances2–5. Here we show a general method for the directed C–H borylation of arenes and heteroarenes without the use of metal catalysts. C7- and C4-borylated indoles are produced by a mild approach that is compatible with a broad range of functional groups. The mechanism, which is established by density functional theory calculations, involves BBr3 acting as both a reagent and a catalyst. The potential utility of this strategy is highlighted by the downstream transformation of the formed boron species into natural products and drug scaffolds.

Suggested Citation

  • Jiahang Lv & Xiangyang Chen & Xiao-Song Xue & Binlin Zhao & Yong Liang & Minyan Wang & Liqun Jin & Yu Yuan & Ying Han & Yue Zhao & Yi Lu & Jing Zhao & Wei-Yin Sun & Kendall. N. Houk & Zhuangzhi Shi, 2019. "Metal-free directed sp2-C–H borylation," Nature, Nature, vol. 575(7782), pages 336-340, November.
    • Handle: RePEc:nat:nature:v:575:y:2019:i:7782:d:10.1038_s41586-019-1640-2
    DOI: 10.1038/s41586-019-1640-2
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41586-019-1640-2
    File Function: Abstract
    Download Restriction: Access to the full text of the articles in this series is restricted.
    File URL: https://libkey.io/10.1038/s41586-019-1640-2?utm_source=ideas
    LibKey link: if access is restricted and if your library uses this service, LibKey will redirect you to where you can use your library subscription to access this item
    ---><---

    As the access to this document is restricted, you may want to search for a different version of it.

    Citations

    Citations are extracted by the CitEc Project, subscribe to its RSS feed for this item.
    as


    Cited by:

    1. Peng Wang & Jiang Liu & Xiaomei Zhu & Kenry & Zhengqing Yan & Jiahui Yan & Jitong Jiang & Manlin Fu & Jingyan Ge & Qing Zhu & Yuguo Zheng, 2023. "Modular synthesis of clickable peptides via late-stage maleimidation on C(7)-H tryptophan," Nature Communications, Nature, vol. 14(1), pages 1-14, December.

    More about this item

    Statistics

    Access and download statistics

    Corrections

    All material on this site has been provided by the respective publishers and authors. You can help correct errors and omissions. When requesting a correction, please mention this item's handle: RePEc:nat:nature:v:575:y:2019:i:7782:d:10.1038_s41586-019-1640-2. See general information about how to correct material in RePEc.

    If you have authored this item and are not yet registered with RePEc, we encourage you to do it here. This allows to link your profile to this item. It also allows you to accept potential citations to this item that we are uncertain about.

    We have no bibliographic references for this item. You can help adding them by using this form .

    If you know of missing items citing this one, you can help us creating those links by adding the relevant references in the same way as above, for each refering item. If you are a registered author of this item, you may also want to check the "citations" tab in your RePEc Author Service profile, as there may be some citations waiting for confirmation.

    For technical questions regarding this item, or to correct its authors, title, abstract, bibliographic or download information, contact: Sonal Shukla or Springer Nature Abstracting and Indexing (email available below). General contact details of provider: http://www.nature.com .

    Please note that corrections may take a couple of weeks to filter through the various RePEc services.

    IDEAS is a RePEc service. RePEc uses bibliographic data supplied by the respective publishers.