Skip to main content
SpringerLink
Log in

NFSI and Its Analogues’ Fluorination for Preparing Aryl Fluorides

  • Living reference work entry
  • First Online:
Fluorination

Part of the book series: Synthetic Organofluorine Chemistry ((SYOC))

  • 138 Accesses

N-Fluorobenzenesulfonimide (NFSI, 1) was first reported by Differding and coworkers in 1991 and soon became popular owing to its suitable reactivity, ready availability, and operational simplicity [1]. Prior to the development of NFSI, N-fluor-N-alkylsulfonamides 2 [2], DesMarteau’s reagent (3) [3], and perfluoro-[N-fluoro-N-(4-pyridyl)-methanesulfonamide] (4) [4] had found application in some electrophilic aromatic substitution reactions (Fig. 1). Generally, the direct fluorination of (hetero)aromatics with NFSI and its analogues is influenced by both the electrophilicity of the “F+” sources and the nucleophilicity of the electron nature of the aromatic substrates.

Fig. 1
figure 1

Structures of several N-fluorosulfonimide reagents

Full size image

This is a preview of subscription content, log in via an institution to check access.

Access this chapter

Log in via an institution

Institutional subscriptions

References

  1. (a) Differding, E.; Ofner, H. Synlett 1991, 187. (b) Lal, G. S.; Pez, G. P.; Syvret, R. G. Chem. Rev. 1996, 96, 1737. (c) Campbell, M. G.; Ritter, T. Chem. Rev. 2015, 115, 612. (d) Champagne, P. A.; Desroches, J.; Hamel, J. D.; Vandamme, M.; Paquin, J. F. Chem. Rev. 2015, 115, 9073.

    Google Scholar 

  2. Barnette, W. E. J. Am. Chem. Soc. 1984, 106, 452.

    Article  CAS  Google Scholar 

  3. Singh, S.; DesMarteau, D. D.; Zuberi, S. S.; Witz, M.; Huang, H-N. J. Am. Chem. Soc. 1987, 109, 7194.

    Article  CAS  Google Scholar 

  4. Banks, R. E.; Khazaei, A. J. Fluorine Chem. 1990, 46, 297.

    Article  CAS  Google Scholar 

  5. (a) Snieckus, V.; Beaulieu, F.; Mohri, K.; Han, W.; Murphy, C. K.; Davis, F. A. Tetrahedron Lett. 1994, 35, 3465. (b) Davis, F. A.; Han, W.; Murphy, C. K. J. Org. Chem. 1995, 60, 4730.

    Google Scholar 

  6. Lal, G. S. U.S. Patent 5,233,074, 1993.

    Google Scholar 

  7. (a) Taylor, E. C.; Zhou, P. Org. Prep. Proced. Int. 1997, 29, 221. (b) Sakamoto, Y.; Komatsu, S.; Suzuki, T. J. Am. Chem. Soc. 2001, 123, 4643. (c) Lai, G.; Guo, T. Syn. Commun. 2008, 38, 72. (d) Wang, W.; Xu, T.; Liang, Y.; Wu, Y.; Li, G.; Yu, L. J. Am. Chem. Soc. 2011, 133, 1885. (e) Gohier, F.; Frere, P.; Roncali, J. J. Org. Chem. 2013, 78, 1497.

    Google Scholar 

  8. Briner, P. H.; Fyfe, M. C. T.; Martin, P.; Murray, P. J.; Naud, F.; Procter, M. J. Org. Process Res. Dev. 2006, 10, 346.

    Article  CAS  Google Scholar 

  9. Ghosh, A. K.; Lagisetty, P.; Zajc, B. J. Org. Chem. 2007, 72, 8222.

    Article  CAS  Google Scholar 

  10. Bellamy, E.; Bayh, O.; Hoarau, C.; Trecourt, F.; Queguiner, G.; Marsais, F. Chem. Commun. 2010, 46, 7043.

    Article  CAS  Google Scholar 

  11. Yamada, S.; Gavryushin, A.; Knochel, P. Angew. Chem. Int. Ed. 2010, 49, 2215.

    Article  CAS  Google Scholar 

  12. Yamada, S.; Knochel, P. Synthesis 2010, 2490.

    Google Scholar 

  13. Nagaki, A.; Uesugi, Y.; Kim, H.; Yoshida, J. Chem. Asian J. 2013, 8, 705.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Key Laboratory of Organofluorine Chemistry, Center for Excellence in Molecular Synthesis, Shanghai Institute of Organic Chemistry, University of Chinese Academy of Sciences, Chinese Academy of Sciences, Shanghai, China

    Jingyu Hu & Jinbo Hu

Authors
  1. Jingyu Hu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Jinbo Hu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Jinbo Hu .

Editor information

Editors and Affiliations

  1. Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China

    Jinbo Hu

  2. R&D Center, Zhejiang Jiuzhou Pharmaceutical Co., Ltd, Taizhou, Zhejiang, China

    Teruo Umemoto

Rights and permissions

Reprints and permissions

Copyright information

© 2020 Springer Nature Singapore Pte Ltd.

About this entry

Check for updates. Verify currency and authenticity via CrossMark

Cite this entry

Hu, J., Hu, J. (2020). NFSI and Its Analogues’ Fluorination for Preparing Aryl Fluorides. In: Hu, J., Umemoto, T. (eds) Fluorination. Synthetic Organofluorine Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-10-1855-8_52-1

Download citation

  • DOI: https://doi.org/10.1007/978-981-10-1855-8_52-1

  • Received:

  • Accepted:

  • Published:

  • Publisher Name: Springer, Singapore

  • Print ISBN: 978-981-10-1855-8

  • Online ISBN: 978-981-10-1855-8

  • eBook Packages: Springer Reference Chemistry and Mat. ScienceReference Module Physical and Materials ScienceReference Module Chemistry, Materials and Physics

Publish with us

Policies and ethics

Search

Navigation