IDEAS home Printed from https://ideas.repec.org/a/nat/nature/v640y2025i8057d10.1038_s41586-025-08784-8.html
   My bibliography  Save this article

Photoinduced copper-catalysed deracemization of alkyl halides

Author

Listed:
  • Feng Zhong

    (California Institute of Technology)

  • Renhe Li

    (California Institute of Technology)

  • Binh Khanh Mai

    (University of Pittsburgh)

  • Peng Liu

    (University of Pittsburgh)

  • Gregory C. Fu

    (California Institute of Technology)

Abstract

Deracemization is an emerging strategy for generating enantioenriched compounds wherein the two enantiomers of a readily available racemic starting material are transformed into a single enantiomer, typically through the action of a light-induced catalyst1,2. Excellent proof of principle for this potentially powerful approach to asymmetric catalysis has been described3–8; nevertheless, substantial challenges have not yet been addressed, including the exploitation of carbon–heteroatom (rather than only carbon–hydrogen and carbon–carbon) bond cleavage to achieve deracemization, as well as the development of processes that provide broad classes of useful enantioenriched compounds and tetrasubstituted stereocentres. Here we describe a straightforward method that addresses these challenges, using a chiral copper catalyst, generated in situ from commercially available components, to achieve the photoinduced deracemization of tertiary (and secondary) alkyl halides through carbon–halogen bond cleavage. Mechanistic studies (including the independent synthesis of postulated intermediates, photophysical, spectroscopic and reactivity studies, and density functional theory calculations) provide support for the key steps and intermediates in our proposed catalytic cycle, as well as insight into the origin of enantioselectivity.

Suggested Citation

  • Feng Zhong & Renhe Li & Binh Khanh Mai & Peng Liu & Gregory C. Fu, 2025. "Photoinduced copper-catalysed deracemization of alkyl halides," Nature, Nature, vol. 640(8057), pages 107-113, April.
  • Handle: RePEc:nat:nature:v:640:y:2025:i:8057:d:10.1038_s41586-025-08784-8
    DOI: 10.1038/s41586-025-08784-8
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41586-025-08784-8
    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/s41586-025-08784-8?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.

    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:640:y:2025:i:8057:d:10.1038_s41586-025-08784-8. 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.