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Modular click chemistry libraries for functional screens using a diazotizing reagent

Author

Listed:
  • Genyi Meng

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

  • Taijie Guo

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

  • Tiancheng Ma

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

  • Jiong Zhang

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

  • Yucheng Shen

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

  • Karl Barry Sharpless

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

  • Jiajia Dong

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

Abstract

Click chemistry is a concept in which modular synthesis is used to rapidly find new molecules with desirable properties1. Copper(i)-catalysed azide–alkyne cycloaddition (CuAAC) triazole annulation and sulfur(vi) fluoride exchange (SuFEx) catalysis are widely regarded as click reactions2–4, providing rapid access to their products in yields approaching 100% while being largely orthogonal to other reactions. However, in the case of CuAAC reactions, the availability of azide reagents is limited owing to their potential toxicity and the risk of explosion involved in their preparation. Here we report another reaction to add to the click reaction family: the formation of azides from primary amines, one of the most abundant functional groups5. The reaction uses just one equivalent of a simple diazotizing species, fluorosulfuryl azide6–11 (FSO2N3), and enables the preparation of over 1,200 azides on 96-well plates in a safe and practical manner. This reliable transformation is a powerful tool for the CuAAC triazole annulation, the most widely used click reaction at present. This method greatly expands the number of accessible azides and 1,2,3-triazoles and, given the ubiquity of the CuAAC reaction, it should find application in organic synthesis, medicinal chemistry, chemical biology and materials science.

Suggested Citation

  • 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.
  • Handle: RePEc:nat:nature:v:574:y:2019:i:7776:d:10.1038_s41586-019-1589-1
    DOI: 10.1038/s41586-019-1589-1
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    Cited by:

    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. 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.
    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. 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.
    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.
    6. 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.

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