IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v13y2022i1d10.1038_s41467-022-31089-7.html
   My bibliography  Save this article

Photoredox catalytic radical fluorosulfonylation of olefins enabled by a bench-stable redox-active fluorosulfonyl radical precursor

Author

Listed:
  • Peng Wang

    (Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University)

  • Honghai Zhang

    (Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University)

  • Xingliang Nie

    (Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University)

  • Tianxiao Xu

    (Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University)

  • Saihu Liao

    (Key Laboratory of Molecule Synthesis and Function Discovery (Fujian Province University), State Key Laboratory of Photocatalysis on Energy and Environment, College of Chemistry, Fuzhou University
    Beijing National Laboratory of Molecular Science (BNLMS))

Abstract

Sulfonyl fluorides have attracted considerable and growing research interests from various disciplines, which raises a high demand for novel and effective methods to access this class of compounds. Radical flurosulfonylation is recently emerging as a promising approach for the synthesis of sulfonyl fluorides. However, the scope of applicable substrate and reaction types are severely restricted by limited known radical reagents. Here, we introduce a solid state, redox-active type of fluorosulfonyl radical reagents, 1-fluorosulfonyl 2-aryl benzoimidazolium triflate (FABI) salts, which enable the radical fluorosulfonylation of olefins under photoredox conditions. In comparison with the known radical precursor, gaseous FSO2Cl, FABI salts are bench-stable, easy to handle, affording high yields in the radical fluorosulfonylation of olefins with before challenging substrates. The advantage of FABIs is further demonstrated in the development of an alkoxyl-fluorosulfonyl difunctionalization reaction of olefins, which forges a facile access to useful β-alkoxyl sulfonyl fluorides and related compounds, and would thus benefit the related study in the context of chemical biology and drug discovery in the future.

Suggested Citation

  • Peng Wang & Honghai Zhang & Xingliang Nie & Tianxiao Xu & Saihu Liao, 2022. "Photoredox catalytic radical fluorosulfonylation of olefins enabled by a bench-stable redox-active fluorosulfonyl radical precursor," Nature Communications, Nature, vol. 13(1), pages 1-10, December.
  • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-31089-7
    DOI: 10.1038/s41467-022-31089-7
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-022-31089-7
    File Function: Abstract
    Download Restriction: no

    File URL: https://libkey.io/10.1038/s41467-022-31089-7?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. Genyi Meng & Taijie Guo & Tiancheng Ma & Jiong Zhang & Yucheng Shen & Karl Barry Sharpless & Jiajia Dong, 2019. "Modular click chemistry libraries for functional screens using a diazotizing reagent," Nature, Nature, vol. 574(7776), pages 86-89, October.
    2. Ruting Xu & Tianxiao Xu & Mingcheng Yang & Tianpeng Cao & Saihu Liao, 2019. "A rapid access to aliphatic sulfonyl fluorides," Nature Communications, Nature, vol. 10(1), pages 1-7, 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. Jian Rong & Ahmed Haider & Troels E. Jeppesen & Lee Josephson & Steven H. Liang, 2023. "Radiochemistry for positron emission tomography," Nature Communications, Nature, vol. 14(1), pages 1-23, December.
    2. Junkai Guo & Xiu Wang & Chuanfa Ni & Xiaolong Wan & Jinbo Hu, 2022. "SulfoxFluor-enabled deoxyazidation of alcohols with NaN3," Nature Communications, Nature, vol. 13(1), pages 1-8, December.
    3. Kazuki Yamamoto & Toyotaka Sato & Aili Hao & Kenta Asao & Rintaro Kaguchi & Shintaro Kusaka & Radhakrishnam Raju Ruddarraju & Daichi Kazamori & Kiki Seo & Satoshi Takahashi & Motohiro Horiuchi & Shin-, 2024. "Development of a natural product optimization strategy for inhibitors against MraY, a promising antibacterial target," Nature Communications, Nature, vol. 15(1), pages 1-15, December.
    4. Soo Bok Kim & Dong Hyeon Kim & Han Yong Bae, 2024. "“On-Water” accelerated dearomative cycloaddition via aquaphotocatalysis," Nature Communications, Nature, vol. 15(1), pages 1-11, December.
    5. Minlong Wang & Jiaman Hou & Hainam Do & Chao Wang & Xiaohe Zhang & Ying Du & Qixin Dong & Lijun Wang & Ke Ni & Fazheng Ren & Jie An, 2024. "Intramolecular chalcogen bonding activated SuFEx click chemistry for efficient organic-inorganic linking," Nature Communications, Nature, vol. 15(1), pages 1-12, December.
    6. Semih Sevim & Roger Sanchis-Gual & Carlos Franco & Albert C. Aragonès & Nadim Darwish & Donghoon Kim & Rosaria Anna Picca & Bradley J. Nelson & Eliseo Ruiz & Salvador Pané & Ismael Díez-Pérez & Josep , 2024. "Electrostatic catalysis of a click reaction in a microfluidic cell," 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_s41467-022-31089-7. 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.