IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v13y2022i1d10.1038_s41467-022-32467-x.html
   My bibliography  Save this article

[3+2] Cycloaddition of alkyl aldehydes and alkynes enabled by photoinduced hydrogen atom transfer

Author

Listed:
  • Siya Le

    (Zhejiang Normal University)

  • Ji Li

    (Zhejiang Normal University)

  • Jian Feng

    (Zhejiang Normal University)

  • Zuxiao Zhang

    (Zhejiang Normal University)

  • Yihui Bai

    (Zhejiang Normal University)

  • Zheliang Yuan

    (Zhejiang Normal University)

  • Gangguo Zhu

    (Zhejiang Normal University)

Abstract

[3+2] Cycloaddition is a step- and atom-economic method for the synthesis of five-membered rings. Despite the great success of 1,3-dipolar cycloadditions, the radical [3+2] annulation of alkynes remains a formidable challenge. Herein, a photoinduced decatungstate-catalyzed [3+2] cycloaddition of various internal alkynes using abundant aliphatic aldehydes as a three-carbon synthon is developed, producing elaborate cyclopentanones in 100% atom economy with excellent site-, regio-, and diastereoselectivity under mild conditions. The catalytic cycle consists of hydrogen atom abstraction from aldehydes, radical addition, 1,5-hydrogen atom transfer, anti-Baldwin 5-endo-trig cyclization, and back hydrogen abstraction. The power of this method is showcased by the late-stage elaboration of medicinally relevant molecules and total or formal synthesis of (±)-β-cuparenone, (±)-laurokamurene B, and (±)-cuparene.

Suggested Citation

  • Siya Le & Ji Li & Jian Feng & Zuxiao Zhang & Yihui Bai & Zheliang Yuan & Gangguo Zhu, 2022. "[3+2] Cycloaddition of alkyl aldehydes and alkynes enabled by photoinduced hydrogen atom transfer," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-32467-x
    DOI: 10.1038/s41467-022-32467-x
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-022-32467-x
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-022-32467-x?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. Yuwei Hong & Jiayan Qiu & Zhenzhen Wu & Sangxuan Xu & Hanliang Zheng & Gangguo Zhu, 2024. "Tetrafluoroisopropylation of alkenes and alkynes enabled by photocatalytic consecutive difluoromethylation with CF2HSO2Na," Nature Communications, Nature, vol. 15(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:13:y:2022:i:1:d:10.1038_s41467-022-32467-x. 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.