IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v13y2022i1d10.1038_s41467-022-30287-7.html
   My bibliography  Save this article

Construction of boron-stereogenic compounds via enantioselective Cu-catalyzed desymmetric B–H bond insertion reaction

Author

Listed:
  • Guan Zhang

    (Fujian Province University, College of Chemistry at Fuzhou University)

  • Zhihan Zhang

    (Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology)

  • Mengyuan Hou

    (Fujian Province University, College of Chemistry at Fuzhou University)

  • Xinping Cai

    (Fujian Province University, College of Chemistry at Fuzhou University)

  • Kai Yang

    (Fujian Province University, College of Chemistry at Fuzhou University)

  • Peiyuan Yu

    (Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology)

  • Qiuling Song

    (Fujian Province University, College of Chemistry at Fuzhou University
    Guangdong Provincial Key Laboratory of Catalysis, Southern University of Science and Technology
    Institute of Next Generation Matter Transformation, College of Materials Science Engineering at Huaqiao University 668 Jimei Boulevard
    School of Chemistry and Chemical Engineering, Henan Normal University)

Abstract

Compared with the well-developed carbon-stereogenic chemistry, the construction of boron-stereogenic compounds remains undeveloped and challenging. Herein, the previously elusive catalytic enantioselective construction of boron-stereogenic compounds has been achieved through enantioselective desymmetric B–H bond insertion reaction. The B–H bond insertion reaction of 2-arylpyridine-boranes with versatile diazo compounds under chiral copper catalyst can afford boron-stereogenic compounds with good to excellent enantioselectivity. Moreover, the synthetic utility of this reaction is demonstrated by the scalability and downstream transformations. DFT calculations provide insights into the reaction mechanism and the origin of stereoselectivity.

Suggested Citation

  • Guan Zhang & Zhihan Zhang & Mengyuan Hou & Xinping Cai & Kai Yang & Peiyuan Yu & Qiuling Song, 2022. "Construction of boron-stereogenic compounds via enantioselective Cu-catalyzed desymmetric B–H bond insertion reaction," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30287-7
    DOI: 10.1038/s41467-022-30287-7
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-022-30287-7
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-022-30287-7?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
    ---><---

    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:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30287-7. 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.