IDEAS home Printed from https://ideas.repec.org/a/nat/natcom/v13y2022i1d10.1038_s41467-022-30132-x.html
   My bibliography  Save this article

SulfoxFluor-enabled deoxyazidation of alcohols with NaN3

Author

Listed:
  • Junkai Guo

    (University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Xiu Wang

    (University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Chuanfa Ni

    (University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Xiaolong Wan

    (University of Chinese Academy of Sciences, Chinese Academy of Sciences)

  • Jinbo Hu

    (University of Chinese Academy of Sciences, Chinese Academy of Sciences)

Abstract

Direct deoxyazidation of alcohols with NaN3 is a straightforward method for the synthesis of widely used alkyl azides in organic chemistry. However, known methods have some limitations such as high reaction temperatures and narrow substrate scope. Herein, a general and practical method for the preparation of alkyl azides from alcohols using NaN3 has been developed. N-tosyl-4-chlorobenzenesulfonimidoyl fluoride (SulfoxFluor) plays an important role in this deoxyazidation process, which converts a broad range of alcohols into alkyl azides at room temperature. The power of this deoxyazidation protocol has been demonstrated by successful late-stage deoxyazidation of natural products and pharmaceutically relevant molecules.

Suggested Citation

  • 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.
    • Handle: RePEc:nat:natcom:v:13:y:2022:i:1:d:10.1038_s41467-022-30132-x
    DOI: 10.1038/s41467-022-30132-x
    as

    Download full text from publisher

    File URL: https://www.nature.com/articles/s41467-022-30132-x
    File Function: Abstract
    Download Restriction: no
    File URL: https://libkey.io/10.1038/s41467-022-30132-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
    ---><---

    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.
    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. 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.
    2. 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.
    3. 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.
    4. 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.
    5. 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_s41467-022-30132-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.

    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.