IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v14y2023i1d10.1038_s41467-023-42392-2.html
   My bibliography  Save this article

Mechanistic insights into excited-state palladium catalysis for C–S bond formations and dehydrogenative sulfonylation of amines

Author

Listed:
  • Krishnamoorthy Muralirajan

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

  • Rajesh Kancherla

    (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))

  • 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))

Abstract

Photocatalytic selective C(sp3)–H activation/cross-coupling reactions are appealing in organic synthesis. In this manuscript, we describe the development of photoexcited-state Pd-catalyzed dehydrogenative β-sulfonylation reactions using amines and aryl sulfonyl chlorides via intermolecular hydrogen atom transfer and C−S cross-coupling processes at room temperature. The transformation can be achieved by the direct generation of two distinct Pd-radical hybrid species and their capability to promote two different reactivities from Pd(0) and aryl sulfonyl chlorides, allowing for the efficient conversion of readily available amines into stable sulfonyl-substituted enamines at room temperature. The in-depth experimental, computational, and transient optical spectroscopic study and catalytic applications of a dehydrogenative functionalization event provide evidence for both static and dynamic quenching, as well as inner-sphere and outer-sphere mechanisms.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:14:y:2023:i:1:d:10.1038_s41467-023-42392-2
    DOI: 10.1038/s41467-023-42392-2
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-023-42392-2
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-023-42392-2?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
    ---><---

    References listed on IDEAS

    as
    1. 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.
    Full references (including those not matched with items on IDEAS)

    Most related items

    These are the items that most often cite the same works as this one and are cited by the same works as this one.
    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.

    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:14:y:2023:i:1:d:10.1038_s41467-023-42392-2. 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.

    If CitEc recognized a bibliographic reference but did not link an item in RePEc to it, you can help with 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.