Skip to main content
SpringerLink
Log in

Copper-Mediated Fluorination for Preparing Aryl Fluorides

  • Living reference work entry
  • First Online:
Fluorination

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

  • 291 Accesses

Introduction

Functionalized aryl fluorides are important motifs because of their widespread application in pharmaceuticals, agrochemicals, materials, and medical diagnosis (positron emission tomography, PET) [1]. As a result, the development of efficient and practical procedures for the construction of aryl C–F bonds has received much attention. Recently, a series of transition metals have been explored for preparing aryl fluorides [2, 3]. Inexpensive metals such as copper have emerged as alternative mediators of C−F bond formation [4]. This section mainly focused on recent advances in copper-mediated/-catalyzed fluorination reactions to construct aryl fluorides. Among these reactions, the fluoride sources could be divided into nucleophilic fluorinating reagents and electrophilic fluorinating reagents (Scheme 1).

Scheme 1
scheme 1

Copper-mediated arene fluorination

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) Purser, S.; Moore, P. R.; Swallow, S.; Gouverneur, V. Chem. Soc. Rev. 2008, 37, 320. (b) Kirk, K. L. Org. Process Res. Dev. 2008, 12, 305. (c) Müller, K.; Faeh, C.; Diederich, F. Science 2007, 317, 1881. (d) Josse, O.; Labar, D.; Georges, B.; Gregoire, V.; Marchand-Brynaert, J. Bioorg. Med. Chem. 2001, 9, 665. (e) Miller, P. W.; Long, N. J.; Vilar, R.; Gee, A. D. Angew. Chem. Int. Ed. 2008, 47, 8998. (f) Ametamey, S. M.; Honer, M.; Schubiger, P. A. Chem. Rev. 2008, 108, 1501. (g) Tredwell, M.; Gouverneur, V. Angew. Chem. Int. Ed. 2012, 51, 11426.

    Google Scholar 

  2. For silver-mediated or -catalyzed aromatic fluorination, see: (a) Furuya, T.; Strom, A. E.; Ritter, T. J. Am. Chem. Soc. 2009, 131, 1662. (b) Tang, P.; Furuya, T.; Ritter, T. J. Am. Chem. Soc. 2010, 132, 12150. (c) Furuya, T.; Ritter, T. Org. Lett. 2009, 11, 2860.

    Google Scholar 

  3. For palladium-mediated or -catalyzed aromatic fluorination, see: (a) Furuya, T.; Ritter, T. J. Am. Chem. Soc. 2008, 130, 10060. (b) Watson, D. A.; Su, M.; Teverovskiy, G.; Zhang, Y.; García-Fortanet,J.; Kinzel, T.; Buchwald, S. L. Science 2009, 325, 1661. (c) Noël, T.; Maimone, T. J.; Buchwald, S. L. Angew. Chem. Int. Ed. 2011, 50, 8900. (d) Mazzotti, A. R.; Campbell, M. G.; Tang, P.; Murphy, J. M.; Ritter, T. J. Am. Chem. Soc. 2013, 135, 14012. (e) Lee, H. G.; Milner, P. J.; Buchwald, S. L. Org. Lett. 2013, 15, 5602. (f) Lee, H. G.; Milner, P. J.; Buchwald, S. L. J. Am. Chem. Soc. 2014, 136, 3792.

    Google Scholar 

  4. Mu, X.; Liu, G. Org. Chem. Front. 2014, 1, 430.

    Article  CAS  Google Scholar 

  5. Fier, P. S.; Hartwig, J. F. J. Am. Chem. Soc. 2012, 134, 10795.

    Article  CAS  Google Scholar 

  6. Mu, X.; Zhang, H.; Chen, P.; Liu, G. Chem. Sci. 2014, 5, 275.

    Article  CAS  Google Scholar 

  7. For reviews on diaryliodonium salts, see: (a) Zhdankin, V. V. Chem. Rev. 2002, 102, 2523. (b) Deprez, N. R.; Sanford, M. S. Inorg. Chem. 2007, 46, 1924. (c) Zhdankin, V. V.; Stang, P. J. Chem. Rev. 2008, 108, 5299. (d) Merritt, E. A.; Olofsson, B. Angew. Chem., Int. Ed. 2009, 48, 9052.

    Google Scholar 

  8. For selected examples, see: (a) Jalalian, N.; Ishikawa, E. E.; Silva, L. F.; Olofsson, B. Org. Lett. 2011, 13, 1552. (b) Laudge, K. P.; Jang, K. S.; Lee, S. Y.; Chi, D. Y. J. Org. Chem. 2012, 77, 5705. (c) Umierski, N.; Manolikakes, G. Org. Lett. 2013, 15, 188. (d) Wagner, A. M.; Sanford, M. S. J. Org. Chem. 2014, 79, 2263.

    Google Scholar 

  9. For selected examples, see: (a) Lv, T.; Wang, Z.; You, J.; Lan, J.; Gao, G. J. Org. Chem. 2013, 78, 5723. (b) Cullen, S. C.; Shekhar, S.; Nere, N. K. J. Org. Chem. 2013, 78, 12194. (c) Sokolovs, I.; Lubriks, D.; Suna, E. J. Am. Chem. Soc. 2014, 136, 6920. (d) Fañanás-Mastral, M.; Feringa, B. L. J. Am. Chem. Soc. 2014, 136, 9894.

    Google Scholar 

  10. (a) Ichiishi, N.; Canty, A. J.; Yates, B. F.; Sanford, M. S. Org. Lett. 2013, 15, 5134. (b) Ichiishi, N.; Canty, A. J.; Yates, B. F.; Sanford, M. S. Organometallics 2014, 33, 5525.

    Google Scholar 

  11. Fier, P. S.; Luo, J.; Hartwig, J. F. J. Am. Chem. Soc. 2013, 135, 2552.

    Article  CAS  Google Scholar 

  12. Ye, Y.; Sanford, M. S. J. Am. Chem. Soc. 2013, 135, 4648.

    Article  CAS  Google Scholar 

  13. Ye, Y.; Schimler, S. D.; Hanley, P. S.; Sanford, M. S. J. Am. Chem. Soc. 2013, 135, 16292.

    Article  CAS  Google Scholar 

  14. Gamache, R. F.; Waldmann, C.; Murphy, J. M. Org. Lett. 2016, 18, 4522.

    Article  CAS  Google Scholar 

  15. Truong, T.; Klimovica, K.; Daugulis, O. J. Am. Chem. Soc. 2013, 135, 9342.

    Article  CAS  Google Scholar 

  16. (a) Cai, L.; Lu, S.; Pike, V. W. Eur. J. Org. Chem. 2008, 2853. (b) Ametamey, S. M.; Honer, M.; Schubiger, P. A. Chem. Rev. 2008, 108, 1501. (c) Littich, R.; Scott, P. J. H. Angew. Chem., Int. Ed. 2012, 51, 1106.

    Google Scholar 

  17. Preshlock, S.; Tredwell, M.; Gouverneur, V. Chem. Rev. 2016, 116, 719.

    Article  CAS  Google Scholar 

  18. (a) Ichiishi, N.; Brooks, A. F.; Topczewski, J. J.; Rodnick, M. E.; Sanford, M. S.; Scott, P. J. H. Org. Lett. 2014, 16, 3224. (b) Mossine, A. V.; Brooks, A. F.; Makaravage, K. J.; Miller, J. M.; Ichiishi, N.; Sanford, M. S.; Scott, P. J. H. Org. Lett. 2015, 17, 5780. (c) Tredwell, M.; Preshlock, S. M.; Taylor, N. J.; Gruber, S.; Huiban, M.; Passchier, J.; Mercier, J.; Génicot, C.; Gouverneur, V. Angew. Chem., Int. Ed. 2014, 53, 7751. (d) Taylor, N. J.; Emer, E.; Preshlock, S.; Schedler, M.; Tredwell, M.; Verhoog, S.; Mercier, J.; Genicot, C.; Gouverneur, V. J. Am. Chem. Soc. 2017, 139, 8267.

    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, Chinese Academy of Sciences, Shanghai, China

    Wenjun Miao & Jinbo Hu

Authors
  1. Wenjun Miao
    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

© 2019 Springer Nature Singapore Pte Ltd.

About this entry

Check for updates. Verify currency and authenticity via CrossMark

Cite this entry

Miao, W., Hu, J. (2019). Copper-Mediated 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_63-1

Download citation

  • DOI: https://doi.org/10.1007/978-981-10-1855-8_63-1

  • 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