Skip to main content
SpringerLink
Log in

N-Haloimide/HF Dethiofluorination

  • Living reference work entry
  • Latest version View entry history
  • First Online:
Fluorination

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

  • 153 Accesses

Introduction

Synthetic methods for organofluorine compounds[1] are categorized roughly into two types [2]: (1) fluorination and (2) use of fluorinated building blocks. Fluorination is further classified into three classes depending on the nature of fluorinating species: (1) electrophilic fluorination (from C-H to C-F using F2 or electrophilic agents), (2) nucleophilic fluorination (from C-Lv (Lv: leaving group) to C-F using fluoride reagents), and (3) deoxofluorination (replacement of hydroxyl or carbonyl groups with one or two fluorides, respectively).

Nucleophilic fluorination is the most accessible reaction, since fluoride ion reagents are stable and easy to handle. However, a fluoride ion is a hard base and poor nucleophile, although bifluoride F- (HF) (or HF2-) and dihydrogen trifluoride F- (HF)2 (or H2F3-) are deemed better nucleophiles. Accordingly, a reactive enough leaving group is essential for successful nucleophilic fluorination. Halogens (Cl, Br, and I), tosylates, and/or...

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. Banks, R. E.; Smart, B. E.; Tatlow, J. C. Organofluorine Chemistry Principles and Commercial Applications Plenum Press, New York and London, 1994. Biomedical Aspects of Fluorine Chemistry Ed. By Filler, R.; Kobayashi Y. Kodansya Ltd. Tokyo and Elsevier Biomedical Press, Amsterdam-New York-Oxford, 1982.

    Book  Google Scholar 

  2. Hiyama, T.; Kanie, K.; Kusumoto, T.; Morizawa, Y.; Shimizu M. Organofluorine Compounds. Chemistry and Applications Springer-Verlag, Berlin, 2000. Synthesis of Fluoroorganic Compounds Ed. By Knunyants, I. L.; Yakobson, G. G. Springer-Verlag, Berlin, 1985.

    Book  Google Scholar 

  3. Mensink, R. A.; Elferink, H.; White, P. B.; Pers, N.; Rutjes, F. P. J. T.; Boltje, T. J. Eur. J. Org. Chem. 2016, 4656–4667.

    Article  CAS  Google Scholar 

  4. Kuroboshi, M.; Hiyama, T. Tetrahedron Lett. 1991, 32, 1215–1218.

    Article  CAS  Google Scholar 

  5. Hara, S.; Kishikawa, Y.; Shirai, A.; Namikawa, T.; Ishihara, S. PCT Int. Appl. 2015, WO2015050229 A1.

    Google Scholar 

  6. Matthews, D. P.; Whitten, J. P.; McCarthy, J. R. Tetrahedron Lett. 1986, 27, 4861–4864.

    Article  CAS  Google Scholar 

  7. Hara, S.; Monoi, M.; Umemura, R.; Fuse, C. Tetrahedron 2012, 68, 10145–10150.

    Article  CAS  Google Scholar 

  8. Furuta, S.; Kuroboshi, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1999, 72, 805–819.

    Article  CAS  Google Scholar 

  9. Kuroboshi, M.; Hiyama, T. J. Synth. Org. Chem. Jpn. 1993, 51, 1124–1133.

    Article  CAS  Google Scholar 

  10. Furuta, S.; Hiyama, T. Synlett 1996, 1199–1200.

    Article  Google Scholar 

  11. Zupan, M.; Bregar, Z. Tetrahedron Lett. 1990, 31, 3357–3358.

    Article  CAS  Google Scholar 

  12. Kuroboshi, M.; Hiyama, T. Tetrahedron Lett. 1992, 33, 4177–4178.

    Article  CAS  Google Scholar 

  13. Kanie, K.; Mizuno, K.; Kuroboshi, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1998, 71, 1973–1991.

    Article  CAS  Google Scholar 

  14. Furuta, S.; Kuroboshi, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1998, 71, 2687–2694.

    Article  CAS  Google Scholar 

  15. Torii, T.; Onishi, T.; Izawa, K. Jpn. Kokai Tokkyo Koho 2006, 052182.

  16. Kanie, K.; Tanaka, Y.; Shimizu, M.; Takehara, S.; Hiyama, T. Chem. Lett. 1997, 827–828.

    Article  Google Scholar 

  17. Kanie, K.; Tanaka, Y.; Suzuki, K.; Kuroboshi, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 471–484.

    Article  CAS  Google Scholar 

  18. Koen, M. J.; Guyader, F. L.; Motherwell, W. B. J. Chem. Soc., Chem. Commun. 1995, 1241–1242.

    Google Scholar 

  19. Kanie, K.; Tanaka, Y.; Shimizu, K.; Kuroboshi, M.; Hiyama, T. Chem. Commun. 1997, 309–310.

    Google Scholar 

  20. Kuroboshi, M.; Hiyama, T. J. Fluorine Chem. 1994, 69, 127–128.

    Article  CAS  Google Scholar 

  21. Kanie, K.; Kuroboshi, M.; Takehara, S.; Hiyama, T. J. Fluorine Chem. 1999, 97, 201–206.

    Article  CAS  Google Scholar 

  22. Ben-David, I.; Rechavi, D.; Mishani, E.; Rozen, S. J. Fluorine Chem. 1999, 97, 75–78.

    Article  CAS  Google Scholar 

  23. Kanie, K.; Takehara, S.; Hiyama, T. Bull. Chem. Soc. Jpn. 2000, 73, 1875–1892.

    Article  CAS  Google Scholar 

  24. Furuta, S.; Kuroboshi, M.; Hiyama, T. Bull. Chem. Soc. Jpn. 1999, 72, 805–819.

    Article  CAS  Google Scholar 

  25. Saulnier, S.; Ciardi, M.; Lppez-Carrillo, V.; Gualandi, A.; Cozzi, P. G. Chem. Euro. J. 2015, 21, 13689–13695.

    Article  CAS  Google Scholar 

  26. Kuroboshi, M.; Hiyama, T. Synlett 1991, 909–910.

    Article  Google Scholar 

  27. Reddy, V. P.; Prakash, G. K. S.; Olah, S. G. A. Adv. Org. Synth. 2006, 2, 183–122.

    CAS  Google Scholar 

  28. Yoshiyama, T.; Fuchigami, T. Chem. Lett. 1992, 1995–1998.

    Article  Google Scholar 

  29. Motherwell, W. B.; Wilkinson, J. A. Synlett 1991, 191–192.

    Article  Google Scholar 

  30. Fuchigami, T.; Inagi, S.; Hayashi, S. Jpn Kokai Tokkyo Koho 2010, JP2010065242.

    Google Scholar 

  31. Kuroboshi, M.; Furuta, S.; Hiyama, T. Tetrahedron Lett. 1995, 36, 6121–6122.

    Article  CAS  Google Scholar 

  32. Ulbrich, D.; Daniliuc, C. G.; Haufe, G. Org. Biomol. Chem. 2016, 14, 2755–2767.

    Article  CAS  Google Scholar 

  33. Hugenberg, V.; Haufe, G. J. Fluorine Chem. 2010, 131, 942–950.

    Article  CAS  Google Scholar 

  34. Hugenberg, V.; Haufe, G. Synlett 2009, 106–108.

    Google Scholar 

  35. Hugenberg, V.; Haufe, G. J. Fluorine Chem. 2012, 143, 238–262.

    Article  CAS  Google Scholar 

  36. Hugenberg, V.; Wagner, S.; Kopka, K.; Schober, O.; Schaefers, M.; Haufe, G. J. Org. Chem. 2010, 75, 6086–6095.

    Article  CAS  Google Scholar 

  37. Kuroboshi, M.; Hiyama, T. Tetrahedron Lett. 1994, 35, 3983–3984.

    Article  CAS  Google Scholar 

  38. Kuroboshi, M.; Hiyama, T. Synlett 1994, 251–252.

    Article  Google Scholar 

  39. Bunnelle, W. H.; McKinnis, B. R.; Narayanan, B. A. J. Org. Chem. 1990, 55, 768–770.

    Article  CAS  Google Scholar 

  40. Fukuhara, T.; Hara, S. Synlett 2009, 198–200.

    Google Scholar 

  41. York, C.; Prakash, G. K. S.; Olah, G. A. Tetrahedron 1996, 52, 9–14.

    Article  CAS  Google Scholar 

  42. Hugenberg, V.; Haufe, G. J. Fluorine Chem. 2012, 143, 238–262.

    Article  CAS  Google Scholar 

  43. York, C.; Prakash, G. K. S.; Olah, G. A. Tetrahedron 1996, 52, 9–14.

    Article  CAS  Google Scholar 

  44. Nicolaou, K. C.; Dolle, R. E.; Papahatjis, D. P.; Randall, J. L. J. Am. Chem. Soc. 1984, 106, 4189–4192.

    Article  CAS  Google Scholar 

  45. Ichikawa, J.; Sugimoto, K.-I.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1987, 1995–1998.

    Google Scholar 

  46. Caddick, S.; Gazzaard, L.; Motherwell, W. B.; Wilkinson, J. A. Tetrahedron 1996, 52, 149–156.

    Article  CAS  Google Scholar 

  47. Dolle, R. E.; Nicolaou, K. C. J. Am. Chem. Soc. 1985, 107, 1691–1694.

    Article  CAS  Google Scholar 

  48. Fuchigami T. Ryusan to Kogyo 2008, 61, 149–154.

    CAS  Google Scholar 

  49. Koemn, M. J.; Le Guyader, F.; Motherwell, W. B. J. Chem. Soc., Chem. Commun. 1995, 1241–1242.

    Google Scholar 

  50. Takahashi, K.; Inagi, S.; Fuchigami, T. J. Electrochem. Soc. 2013, 160, G3046-G3052.

    Article  CAS  Google Scholar 

  51. Fuchigami, T.; Sano, M. J. Electroanal. Chem. 1996, 414, 81–84.

    Article  Google Scholar 

  52. Purrington, S. T.; Pitt, J. H. Tetrahedron Lett. 1988, 29, 6851–6852.

    Article  CAS  Google Scholar 

  53. Kulanthaivel, P.; Pelletier, S. W. Tetrahedron Lett. 1987, 28, 3883–3886.

    Article  CAS  Google Scholar 

  54. Hasegawa, M.; Ishii, H.; Fuchigami, T. Green Chem. 2003, 5, 512–515.

    Article  CAS  Google Scholar 

  55. Ulbrich, D.; Daniliuc, C. G.; Haufe, G. Org. Biomolecular Chem. 2016, 14, 2755–2767.

    Article  CAS  Google Scholar 

  56. Shishimi T.; Hara, S. J. Fluorine Chem. 2014, 168, 55–60.

    Article  CAS  Google Scholar 

  57. Rayala, R.; Giuglio-Tonoko, A.; Broggi, J.; Terme, T.; Vanelle, P.; Theard, P.; Medebielle, M.; Wnuk, S. F. Tetrahedron 2016, 72, 1969–1977.

    Article  CAS  Google Scholar 

  58. Aso, Y.; Ie Y. Jpn. Tokkyo Koho 2013, JP5124081.

    Google Scholar 

  59. Tahara, R.; Fukuhara, T.; Hara, S. J. Fluorine Chem. 2011, 132, 579–586.

    Article  CAS  Google Scholar 

  60. Kanie, K.; Takehara, S.; Hiyama T. Bull. Chem. Soc. Jpn. 2000, 73, 1875–1892.

    Article  CAS  Google Scholar 

  61. Inoue, T.; Fuse, C.; Hara, S. J. Fluorine Chem. 2015, 179, 48–52.

    Article  CAS  Google Scholar 

  62. Kuroboshi, M.; Hiyama, T. Tetrahedron Lett. 1992, 33, 4177–4178.

    Article  CAS  Google Scholar 

  63. Kanie, K.; Mizuno, K.; Kuroboshi, M.; Takehara, S.; Hiyama T. Bull. Chem. Soc. Jpn. 1999, 72, 2523–2535.

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Applied Chemistry, Faculty of Engineering, Okayama University, Okayama, Japan

    Manabu Kuroboshi

  2. Research and Development Initiative, Chuo University, Bunkyo-ku, Tokyo, Japan

    Tamejiro Hiyama

Authors
  1. Manabu Kuroboshi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tamejiro Hiyama
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Manabu Kuroboshi .

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

Kuroboshi, M., Hiyama, T. (2019). N-Haloimide/HF Dethiofluorination. In: Hu, J., Umemoto, T. (eds) Fluorination. Synthetic Organofluorine Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-10-1855-8_3-2

Download citation

  • DOI: https://doi.org/10.1007/978-981-10-1855-8_3-2

  • 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

Chapter history

  1. Latest

    N-Haloimide/HF Dethiofluorination
    Published:
    17 October 2018

    DOI: https://doi.org/10.1007/978-981-10-1855-8_3-2

  2. Original

    N-Haloimide/HF Dethiofluorination
    Published:
    14 October 2017

    DOI: https://doi.org/10.1007/978-981-10-1855-8_3-1

Search

Navigation