IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v15y2024i1d10.1038_s41467-024-53266-6.html
   My bibliography  Save this article

Direct oxygen insertion into C-C bond of styrenes with air

Author

Listed:
  • Qixue Qin

    (Chang Cheng Rd. 700)

  • Liang Zhang

    (Chang Cheng Rd. 700)

  • Jialiang Wei

    (Peking University)

  • Xu Qiu

    (Peking University)

  • Shuanghong Hao

    (Chang Cheng Rd. 700)

  • Xiao-De An

    (Chang Cheng Rd. 700)

  • Ning Jiao

    (Peking University)

Abstract

Skeletal editing of single-atom insertion to basic chemicals has been demonstrated as an efficient strategy for the discovery of structurally diversified compounds. Previous endeavors in skeletal editing have successfully facilitated the insertion of boron, nitrogen, and carbon atoms. Given the prevalence of oxygen atoms in biologically active molecules, the direct oxygenation of C-C bonds through single-oxygen-atom insertion like Baeyer-Villiger reaction is of particular significance. Herein, we present an approach for the skeletal modification of styrenes using O2 via oxygen insertion, resulting in the formation of aryl ether frameworks under mild reaction conditions. The broad functional-group tolerance and the excellent chemo- and regioselectivity are demonstrated in this protocol. A preliminary mechanistic study indicates the potential involvement of 1,2-aryl radical migration in this reaction.

Suggested Citation

  • Qixue Qin & Liang Zhang & Jialiang Wei & Xu Qiu & Shuanghong Hao & Xiao-De An & Ning Jiao, 2024. "Direct oxygen insertion into C-C bond of styrenes with air," Nature Communications, Nature, vol. 15(1), pages 1-7, December.
    • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-53266-6
    DOI: 10.1038/s41467-024-53266-6
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-024-53266-6
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-024-53266-6?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. Evan J. Horn & Brandon R. Rosen & Yong Chen & Jiaze Tang & Ke Chen & Martin D. Eastgate & Phil S. Baran, 2016. "Scalable and sustainable electrochemical allylic C–H oxidation," Nature, Nature, vol. 533(7601), pages 77-81, May.
    2. Jisoo Woo & Colin Stein & Alec H. Christian & Mark D. Levin, 2023. "Carbon-to-nitrogen single-atom transmutation of azaarenes," Nature, Nature, vol. 623(7985), pages 77-82, November.
    3. Sean H. Kennedy & Balu D. Dherange & Kathleen J. Berger & Mark D. Levin, 2021. "Skeletal editing through direct nitrogen deletion of secondary amines," Nature, Nature, vol. 593(7858), pages 223-227, May.
    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. Hong Lu & Yu Zhang & Xiu-Hong Wang & Ran Zhang & Peng-Fei Xu & Hao Wei, 2024. "Carbon–nitrogen transmutation in polycyclic arenol skeletons to access N-heteroarenes," Nature Communications, Nature, vol. 15(1), pages 1-8, December.
    2. Pan Ran & Aoqian Qiu & Tianshu Liu & Fangyuan Wang & Bailin Tian & Beiyao Xiang & Jun Li & Yang Lv & Mengning Ding, 2024. "Universal high-efficiency electrocatalytic olefin epoxidation via a surface-confined radical promotion," Nature Communications, Nature, vol. 15(1), pages 1-12, December.
    3. Haitao Qin & Ting Guo & Ken Lin & Guigen Li & Hongjian Lu, 2023. "Synthesis of dienes from pyrrolidines using skeletal modification," Nature Communications, Nature, vol. 14(1), pages 1-8, December.
    4. Zhiwei Zhao & Ranran Zhang & Yaowen Liu & Zile Zhu & Qiuyan Wang & Youai Qiu, 2024. "Electrochemical C−H deuteration of pyridine derivatives with D2O," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    5. Hanah Na & Liviu M. Mirica, 2022. "Deciphering the mechanism of the Ni-photocatalyzed C‒O cross-coupling reaction using a tridentate pyridinophane ligand," Nature Communications, Nature, vol. 13(1), pages 1-11, December.
    6. Min Liu & Tian Feng & Yanwei Wang & Guangsheng Kou & Qiuyan Wang & Qian Wang & Youai Qiu, 2023. "Metal-free electrochemical dihydroxylation of unactivated alkenes," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    7. Kaifa Du & Enlai Gao & Chunbo Zhang & Yongsong Ma & Peilin Wang & Rui Yu & Wenmiao Li & Kaiyuan Zheng & Xinhua Cheng & Diyong Tang & Bowen Deng & Huayi Yin & Dihua Wang, 2023. "An iron-base oxygen-evolution electrode for high-temperature electrolyzers," Nature Communications, Nature, vol. 14(1), pages 1-8, December.
    8. Hongyu Zhong & Dominic T. Egger & Valentina C. M. Gasser & Patrick Finkelstein & Loris Keim & Merlin Z. Seidel & Nils Trapp & Bill Morandi, 2023. "Skeletal metalation of lactams through a carbonyl-to-nickel-exchange logic," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    9. Zhonghe Wang & Yang Tang & Songtao Liu & Liang Zhao & Huaqing Li & Cheng He & Chunying Duan, 2024. "Energy transfer-mediated multiphoton synergistic excitation for selective C(sp3)–H functionalization with coordination polymer," Nature Communications, Nature, vol. 15(1), pages 1-11, 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:15:y:2024:i:1:d:10.1038_s41467-024-53266-6. 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.