IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v13y2022i1d10.1038_s41467-022-30278-8.html
   My bibliography  Save this article

Mechanistic insights into photochemical nickel-catalyzed cross-couplings enabled by energy transfer

Author

Listed:
  • Rajesh Kancherla

    (King Abdullah University of Science and Technology (KAUST))

  • Krishnamoorthy Muralirajan

    (King Abdullah University of Science and Technology (KAUST))

  • Bholanath Maity

    (King Abdullah University of Science and Technology (KAUST))

  • Safakath Karuthedath

    (King Abdullah University of Science and Technology (KAUST))

  • Gadde Sathish Kumar

    (King Abdullah University of Science and Technology (KAUST))

  • Frédéric Laquai

    (King Abdullah University of Science and Technology (KAUST))

  • Luigi Cavallo

    (King Abdullah University of Science and Technology (KAUST))

  • Magnus Rueping

    (King Abdullah University of Science and Technology (KAUST)
    Institute for Experimental Molecular Imaging (ExMI), RWTH Aachen, University Clinic)

Abstract

Various methods that use a photocatalyst for electron transfer between an organic substrate and a transition metal catalyst have been established. While triplet sensitization of organic substrates via energy transfer from photocatalysts has been demonstrated, the sensitization of transition metal catalysts is still in its infancy. Here, we describe the selective alkylation of C(sp3)–H bonds via triplet sensitization of nickel catalytic intermediates with a thorough elucidation of its reaction mechanism. Exergonic Dexter energy transfer from an iridium photosensitizer promotes the nickel catalyst to the triplet state, thus enabling C–H functionalization via the release of bromine radical. Computational studies and transient absorption experiments support that the reaction proceeds via the formation of triplet states of the organometallic nickel catalyst by energy transfer.

Suggested Citation

  • Rajesh Kancherla & Krishnamoorthy Muralirajan & Bholanath Maity & Safakath Karuthedath & Gadde Sathish Kumar & Frédéric Laquai & Luigi Cavallo & Magnus Rueping, 2022. "Mechanistic insights into photochemical nickel-catalyzed cross-couplings enabled by energy transfer," Nature Communications, Nature, vol. 13(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30278-8
    DOI: 10.1038/s41467-022-30278-8
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-022-30278-8
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-022-30278-8?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
    ---><---

    Citations

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


    Cited by:

    1. Long Huang & Marcin Szewczyk & Rajesh Kancherla & Bholanath Maity & Chen Zhu & Luigi Cavallo & Magnus Rueping, 2023. "Modulating stereoselectivity in allylic C(sp3)-H bond arylations via nickel and photoredox catalysis," Nature Communications, Nature, vol. 14(1), pages 1-10, December.
    2. Krishnamoorthy Muralirajan & Rajesh Kancherla & Bholanath Maity & Safakath Karuthedath & Frédéric Laquai & Luigi Cavallo & Magnus Rueping, 2023. "Mechanistic insights into excited-state palladium catalysis for C–S bond formations and dehydrogenative sulfonylation of amines," Nature Communications, Nature, vol. 14(1), pages 1-12, 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:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30278-8. 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.