IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v16y2025i1d10.1038_s41467-025-59809-9.html
   My bibliography  Save this article

Photochemical C3-amination of pyridines via Zincke imine intermediates

Author

Listed:
  • Kitti Franciska Szabó

    (Institute of Organic Chemistry Polish Academy of Sciences)

  • Piotr Banachowicz

    (Institute of Organic Chemistry Polish Academy of Sciences)

  • Antoni Powała

    (Institute of Organic Chemistry Polish Academy of Sciences
    Department of Chemistry, Warsaw University of Technology)

  • Danijela Lunic

    (Universidad de La Rioja)

  • Ignacio Funes Ardoiz

    (Universidad de La Rioja)

  • Dorota Gryko

    (Institute of Organic Chemistry Polish Academy of Sciences)

Abstract

Selective skeletal and peripheral editing of the pyridine moiety has broadly expanded the chemical space. While C-H functionalization at C2 and C4 positions are enabled by the inherent reactivity of this heteroarene, selective derivatization at the C3 position has long posed a significant challenge. Recently, based on a dearomatization-rearomatization sequence, involving Zincke imine intermediates, selective halogenation (-Br, -Cl, and -I) and isotopic labelling were accomplished. Here, we report a mild and regioselective method for C3-amination that relies on the photochemical reaction of Zincke imine with an amidyl radical generated from N-aminopyridinium salts. Mechanistic and theoretical studies indicate that radical intermediates are involved and explain the C3 regioselectivity of the reaction.

Suggested Citation

  • Kitti Franciska Szabó & Piotr Banachowicz & Antoni Powała & Danijela Lunic & Ignacio Funes Ardoiz & Dorota Gryko, 2025. "Photochemical C3-amination of pyridines via Zincke imine intermediates," Nature Communications, Nature, vol. 16(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-59809-9
    DOI: 10.1038/s41467-025-59809-9
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-025-59809-9
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-025-59809-9?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:16:y:2025:i:1:d:10.1038_s41467-025-59809-9. 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.