IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v15y2024i1d10.1038_s41467-024-45015-6.html
   My bibliography  Save this article

Electrophotocatalytic hydrogenation of imines and reductive functionalization of aryl halides

Author

Listed:
  • Wen-Jie Kang

    (Fudan University)

  • Yanbin Zhang

    (Fudan University)

  • Bo Li

    (California Institute of Technology)

  • Hao Guo

    (Fudan University)

Abstract

The open-shell catalytically active species, like radical cations or radical anions, generated by one-electron transfer of precatalysts are widely used in energy-consuming redox reactions, but their excited-state lifetimes are usually short. Here, a closed-shell thioxanthone-hydrogen anion species (3), which can be photochemically converted to a potent and long-lived reductant, is generated under electrochemical conditions, enabling the electrophotocatalytic hydrogenation. Notably, TfOH can regulate the redox potential of the active species in this system. In the presence of TfOH, precatalyst (1) reduction can occur at low potential, so that competitive H2 evolution can be inhibited, thus effectively promoting the hydrogenation of imines. In the absence of TfOH, the reducing ability of the system can reach a potency even comparable to that of Na0 or Li0, thereby allowing the hydrogenation, borylation, stannylation and (hetero)arylation of aryl halides to construct C−H, C−B, C−Sn, and C−C bonds.

Suggested Citation

  • Wen-Jie Kang & Yanbin Zhang & Bo Li & Hao Guo, 2024. "Electrophotocatalytic hydrogenation of imines and reductive functionalization of aryl halides," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
  • Handle: RePEc:nat:natcom:v:15:y:2024:i:1:d:10.1038_s41467-024-45015-6
    DOI: 10.1038/s41467-024-45015-6
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-024-45015-6
    File Function: Abstract
    Download Restriction: no

    File URL: https://libkey.io/10.1038/s41467-024-45015-6?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. Ian A. MacKenzie & Leifeng Wang & Nicholas P. R. Onuska & Olivia F. Williams & Khadiza Begam & Andrew M. Moran & Barry D. Dunietz & David A. Nicewicz, 2020. "Discovery and characterization of an acridine radical photoreductant," Nature, Nature, vol. 580(7801), pages 76-80, April.
    2. Guo-Quan Sun & Peng Yu & Wen Zhang & Wei Zhang & Yi Wang & Li-Li Liao & Zhen Zhang & Li Li & Zhipeng Lu & Da-Gang Yu & Song Lin, 2023. "Electrochemical reactor dictates site selectivity in N-heteroarene carboxylations," Nature, Nature, vol. 615(7950), pages 67-72, March.
    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. Shun Li & Juan Tang & Yonglin Shi & Meixin Yan & Yihua Fu & Zhishan Su & Jiaqi Xu & Weichao Xue & Xueli Zheng & Yicen Ge & Ruixiang Li & Hua Chen & Haiyan Fu, 2024. "C3 Selective chalcogenation and fluorination of pyridine using classic Zincke imine intermediates," Nature Communications, Nature, vol. 15(1), pages 1-9, December.
    2. Le Zeng & Ling Huang & Wenhai Lin & Lin-Han Jiang & Gang Han, 2023. "Red light-driven electron sacrificial agents-free photoreduction of inert aryl halides via triplet-triplet annihilation," Nature Communications, Nature, vol. 14(1), pages 1-9, December.
    3. 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.
    4. Le Zeng & Ling Huang & Zhi Huang & Tomoyasu Mani & Kai Huang & Chunying Duan & Gang Han, 2024. "Long wavelength near-infrared and red light-driven consecutive photo-induced electron transfer for highly effective photoredox catalysis," Nature Communications, Nature, vol. 15(1), pages 1-10, December.
    5. Björn Pfund & Deyanira Gejsnæs-Schaad & Bruno Lazarevski & Oliver S. Wenger, 2024. "Picosecond reactions of excited radical ion super-reductants," Nature Communications, Nature, vol. 15(1), pages 1-7, December.
    6. Guanqun Han & Guodong Li & Jie Huang & Chuang Han & Claudia Turro & Yujie Sun, 2022. "Two-photon-absorbing ruthenium complexes enable near infrared light-driven photocatalysis," Nature Communications, Nature, vol. 13(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:15:y:2024:i:1:d:10.1038_s41467-024-45015-6. 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.