IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v16y2025i1d10.1038_s41467-025-56372-1.html
   My bibliography  Save this article

Photoredox/Cr-catalyzed enantioselective radical-polar crossover transformation via C-H functionalization

Author

Listed:
  • Si-Yuan Tang

    (ShanghaiTech University)

  • Zhan-Jie Wang

    (ShanghaiTech University)

  • Yu Ao

    (ShanghaiTech University)

  • Ning Wang

    (ShanghaiTech University)

  • Huan-Ming Huang

    (ShanghaiTech University)

Abstract

Asymmetric multicomponent reactions that aim to control multiple chiral centers with high selectivity in a single step remain an on-gonging challenge. The realm of enantioselective radical-polar crossover transformation achieved through C-H Functionalization has yet to be fully explored. Herein, we present a successful description of a photoredox/Cr-catalyzed enantioselective three-component (hetero)arylalkylation of 1,3-dienes through C-H functionalization. A diverse array of chiral homoallylic alcohols could be obtained in good to excellent yields, accompanied by outstanding enantioselectivity. The asymmetric radical-polar crossover transformation could build two chiral centers simultaneously and demonstrates broad substrate tolerance, accommodating various drug-derived aldehydes, (hetero)aromatics, and 1,3-diene derivatives. Preliminary mechanistic studies indicate the involvement of a radical intermediate, with the chiral allylic chromium species reacting with various aliphatic and aromatic aldehydes through Zimmerman–Traxler transition states enabled by dual photoredox and chiral chromium catalysis.

Suggested Citation

  • Si-Yuan Tang & Zhan-Jie Wang & Yu Ao & Ning Wang & Huan-Ming Huang, 2025. "Photoredox/Cr-catalyzed enantioselective radical-polar crossover transformation via C-H functionalization," Nature Communications, Nature, vol. 16(1), pages 1-9, December.
    • Handle: RePEc:nat:natcom:v:16:y:2025:i:1:d:10.1038_s41467-025-56372-1
    DOI: 10.1038/s41467-025-56372-1
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-025-56372-1
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-025-56372-1?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. Feng-Hua Zhang & Xiaochong Guo & Xianrong Zeng & Zhaobin Wang, 2022. "Asymmetric 1,4-functionalization of 1,3-enynes via dual photoredox and chromium catalysis," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    2. 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.
    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. 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.
    2. Long Zou & Xinyue Zheng & XueZheng Yi & Qingquan Lu, 2024. "Asymmetric paired oxidative and reductive catalysis enables enantioselective alkylarylation of olefins with C(sp3)−H bonds," Nature Communications, Nature, vol. 15(1), pages 1-8, 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:16:y:2025:i:1:d:10.1038_s41467-025-56372-1. 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.