IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v13y2022i1d10.1038_s41467-022-28007-2.html
   My bibliography  Save this article

Photocatalytic defluoroalkylation and hydrodefluorination of trifluoromethyls using o-phosphinophenolate

Author

Listed:
  • Can Liu

    (University of Science and Technology of China)

  • Ni Shen

    (University of Science and Technology of China)

  • Rui Shang

    (University of Science and Technology of China
    The University of Tokyo)

Abstract

Under visible light irradiation, o-phosphinophenolate functions as an easily accessible photoredox catalyst to activate trifluoromethyl groups in trifluoroacetamides, trifluoroacetates, and trifluoromethyl (hetero)arenes to deliver corresponding difluoromethyl radicals. It works in relay with a thiol hydrogen atom transfer (HAT) catalyst to enable selective defluoroalkylation and hydrodefluorination. The reaction allows for the facile synthesis of a broad scope of difluoromethylene-incorporated carbonyl and (hetero)aromatic compounds, which are valuable fluorinated intermediates of interest in the pharmaceutical industry. The ortho-diphenylphosphino substituent, which is believed to facilitate photoinduced electron transfer, plays an essential role in the redox reactivity of phenolate. In addition to trifluoromethyl groups, pentafluoroethyl groups could also be selectively defluoroalkylated.

Suggested Citation

  • Can Liu & Ni Shen & Rui Shang, 2022. "Photocatalytic defluoroalkylation and hydrodefluorination of trifluoromethyls using o-phosphinophenolate," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-28007-2
    DOI: 10.1038/s41467-022-28007-2
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-022-28007-2
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-022-28007-2?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
    ---><---

    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_s41467-022-28007-2. 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.