IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v12y2021i1d10.1038_s41467-021-26794-8.html
   My bibliography  Save this article

Catalytic enantioselective reductive domino alkyl arylation of acrylates via nickel/photoredox catalysis

Author

Listed:
  • Pengcheng Qian

    (Nanjing Tech University)

  • Haixing Guan

    (Nanjing Tech University
    Shandong University of Traditional Chinese Medicine)

  • Yan-En Wang

    (Hebei Agricultural University)

  • Qianqian Lu

    (Nanjing Tech University)

  • Fan Zhang

    (Nanjing Tech University)

  • Dan Xiong

    (Nanjing Tech University)

  • Patrick J. Walsh

    (University of Pennsylvania)

  • Jianyou Mao

    (Nanjing Tech University)

Abstract

Nonsteroidal anti-inflammatory drug derivatives (NSAIDs) are an important class of medications. Here we show a visible-light-promoted photoredox/nickel catalyzed approach to construct enantioenriched NSAIDs via a three-component alkyl arylation of acrylates. This reductive cross-electrophile coupling avoids preformed organometallic reagents and replaces stoichiometric metal reductants by an organic reductant (Hantzsch ester). A broad range of functional groups are well-tolerated under mild conditions with high enantioselectivities (up to 93% ee) and good yields (up to 90%). A study of the reaction mechanism, as well as literature precedence, enabled a working reaction mechanism to be presented. Key steps include a reduction of the alkyl bromide to the radical, Giese addition of the alkyl radical to the acrylate and capture of the α-carbonyl radical by the enantioenriched nickel catalyst. Reductive elimination from the proposed Ni(III) intermediate generates the product and forms Ni(I).

Suggested Citation

  • Pengcheng Qian & Haixing Guan & Yan-En Wang & Qianqian Lu & Fan Zhang & Dan Xiong & Patrick J. Walsh & Jianyou Mao, 2021. "Catalytic enantioselective reductive domino alkyl arylation of acrylates via nickel/photoredox catalysis," Nature Communications, Nature, vol. 12(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:12:y:2021:i:1:d:10.1038_s41467-021-26794-8
    DOI: 10.1038/s41467-021-26794-8
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-021-26794-8
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-021-26794-8?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. Yuxi Gao & Lijuan Gao & Endiao Zhu & Yunhong Yang & Mi Jie & Jiaqian Zhang & Zhiqiang Pan & Chengfeng Xia, 2023. "Nickel/photoredox dual catalyzed arylalkylation of nonactivated alkenes," Nature Communications, Nature, vol. 14(1), pages 1-9, 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:12:y:2021:i:1:d:10.1038_s41467-021-26794-8. 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.