Fluorination

Living Edition
| Editors: Jinbo Hu, Teruo Umemoto

Fluorinations in Organic Chemistry with Elemental Fluorine

Living reference work entry
First Online:
Received:
Accepted:
DOI: https://doi.org/10.1007/978-981-10-1855-8_31-1
How to cite

Introduction

There is a common belief that elemental fluorine, even when diluted, is a very dangerous material, extremely reactive, and hence completely unselective. We should be scared even when we only think of it! We can find many statements in the literature reflecting this sentiment: “Highly hazardous,” “use with great care,” “only for well-trained professionals,” “but fluorine – watch it,” “highly toxic,” and so on. (We don’t wish to mention the names of those scientists who otherwise are doing great chemistry, but such statements can be found in some of the most respected publications). Usually such statements come from people who never worked with diluted fluorine and in many cases as an “explanation” why they will work with other reagents frequently inferior to F2/N2mixtures. It should be remembered that dilute fluorine is less dangerous and easier to work with than chlorine, for example, as if released it may spread to much shorter distances, its pressure regulators on the...

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

Notes

Acknowledgment

Studies from this laboratory described in this review have been continuously supported by the Israel Science Foundation.

References

  1. 1.
    American Environmental Group Ltd. AEGL (Acute Exposure Guideline Level) (50), October 2, 2009.Google Scholar
  2. 2.
    Dayan, S.; Kol, M.; Rozen, S. Synthesis 1999, 1427.Google Scholar
  3. 3.
    Pianca, M.; Barchiesi, E.; Esposto, G.; Radice, S. J. Fluorine Chem. 1999, 95, 71.CrossRefGoogle Scholar
  4. 4.
    Tressaud, A.; Durand, E.; Labrugere, C.; Kharitonov, A. P.; Karitonova, L. N. J. Fluorine Chem. 2007, 128, 378.CrossRefGoogle Scholar
  5. 5.
    Belaish, I.; Davidov, D.; Selig, H.; McLean, M. R.; Dalton, L. Angew. Chem. Int. Ed. Engl. Adv. Mater. 1989, 28, 1569.CrossRefGoogle Scholar
  6. 6.
    Kirsch, P.; Bremer, M.; Kirsch, A.; Osterodt, J. J. Am. Chem. Soc. 1999, 121, 11277.CrossRefGoogle Scholar
  7. 7.
    Haiges, R.; Wagner, R.; Boatz, J. A.; Yousufuddin, M.; Etzkorn, M.; Prakash, G. K. S.; Christe, K. O.; Chapman, R. D.; Welker, M. F.; Kreutzberger, C. B. Angew. Chem. 2006, 45, 5179.CrossRefGoogle Scholar
  8. 8.
    Xue, X. S.; Wang, Y.; Li, M.; Cheng, J. P. J. Org. Chem. 2016, 81, 4280.CrossRefGoogle Scholar
  9. 9.
    Shimp, L. A.; Lagow, R. J. J. Org. Chem. 1977, 42, 3437.CrossRefGoogle Scholar
  10. 10.
    Levin, M. D.; Hamrock, S. J.; Kaszynski, P.; Shtarev, A. B.; Levina, G. A.; Noll, B. C.; Ashley, M. E.; Newmark, R.; Moore, G. G. I.; Michl, J. J. Am. Chem. Soc. 1997, 119, 12750.CrossRefGoogle Scholar
  11. 11.
    Callahan, R. P.; Yongstrom, C. R.; Lagow, R. J. J. Organometallic Chem 2000 , 596, 6.CrossRefGoogle Scholar
  12. 12.
    Lin, T. Y. Chang, H. C.; Lagow, R. J. J. Org. Chem. 1999, 64, 8127.CrossRefGoogle Scholar
  13. 13.
    Ono, T.; Yamanouchi, K.; Scherer, K. V. J. Fluorine Chem. 1995, 73, 267.CrossRefGoogle Scholar
  14. 14.
    Hung, M.; Farnham, W. B.; Feiring, A. E.; Rozen, S. J. Am. Chem. Soc. 1993, 115, 8954.CrossRefGoogle Scholar
  15. 15.
    Sievert, A. C.; Tong, W. R.; Napa, M. J. J. Fluorine Chem. 1991, 53, 397.CrossRefGoogle Scholar
  16. 16.
    Rozen, S.; Brand M. J. Org. Chem. 1981, 46, 733.CrossRefGoogle Scholar
  17. 17.
    Hebel, D.; Rozen, S. J. Org. Chem. 1987, 52, 2588.CrossRefGoogle Scholar
  18. 18.
    Namavari, M.; Satyamurthy, N.; Barrio J. R. J. Fluorine Chem. 1995, 74, 113.CrossRefGoogle Scholar
  19. 19.
    Dolle, F.; Demphel, S.; Hinnen, F.; Fornier, D.; Vaufrey, F.; Crouzel, C. J. Lab. Cpd. Radiopharm. 1998, 41, 105.CrossRefGoogle Scholar
  20. 20.
    Barton, D. H. R.; Hesse, R. H.; Markwell, R. E.; Pechet, M. M.; Rozen, S. J. Am. Chem. Soc. 1976, 98, 3036.CrossRefGoogle Scholar
  21. 21.
    Breslow, R. Acc. Chem. Res. 1980, 13, 170.CrossRefGoogle Scholar
  22. 22.
    Rozen, S.; Gal, C. Tetrahedron Lett. 1984, 25, 449.CrossRefGoogle Scholar
  23. 23.
    Fukaya, H.; Morokuma, K. J. Org. Chem. 2003, 68, 8170.CrossRefGoogle Scholar
  24. 24.
    Rozen, S.; Gal, C.; Faust, Y. J. Am. Chem. Soc. 1980, 102, 6861.CrossRefGoogle Scholar
  25. 25.
    Rozen, S.; Gal, C. J. Org. Chem. 1987a, 52, 2769.CrossRefGoogle Scholar
  26. 26.
    Dixon, D. A.; Kleier, D. A.; Lipscomb, W. N. J. Am. Chem. Soc. 1978, 100, 5681.CrossRefGoogle Scholar
  27. 27.
    Rozen, S.; Gal, C. J. Org. Chem. 1987b, 52, 4928.CrossRefGoogle Scholar
  28. 28.
    Rozen, S.; Gal, C. J. Org. Chem. 1988, 53, 2803.CrossRefGoogle Scholar
  29. 29.
    Rozen, S.; Ben-Shoshan, G. J. Org. Chem. 1986, 51, 3522.CrossRefGoogle Scholar
  30. 30.
    Rozen, S.; Ben-Shoshan, G. Org. Magn. Res. 1985, 23, 116.Google Scholar
  31. 31.
    Bornstein, J.; Borden, M. R.; Nunes, F.; Tarlin, H. I. J. Am. Chem. Soc. 1963, 85, 1609.CrossRefGoogle Scholar
  32. 32.
    Sket, B.; Zupan, M. J. Chem. Soc. Perkin Trans. I, 1977, 2169.Google Scholar
  33. 33.
    Shellhamer, D. F.; Conner, R. J.; Richardson, R. E.; Heasley, V. L. J. Org. Chem. 1984, 49, 5015.CrossRefGoogle Scholar
  34. 34.
    Miller, W. T.; Staffer, J. O.; Fuller, J.; Currie, A. C. J. Am. Chem. Soc. 1964, 86, 51.CrossRefGoogle Scholar
  35. 35.
    Scherer, K. V. Jr.; Ono, T.; Yamanouchi, K.; Fernandez, R.; Henderson, P. J. Am. Chem. Soc. 1985, 107, 718.CrossRefGoogle Scholar
  36. 36.
    Rozen, S.; Brand, M. J. Org. Chem. 1986, 51, 3607.CrossRefGoogle Scholar
  37. 37.
    Gatenyo, J.; Rozen, S. J. Fluorine Chem. 2009, 130, 332.CrossRefGoogle Scholar
  38. 38.
    Vints, I.; Rozen, S. Tetrahedron 2016, 72, 632.CrossRefGoogle Scholar
  39. 39.
    Vints, I.; Rozen, S. J. Org. Chem. 2014, 79, 7261.CrossRefGoogle Scholar
  40. 40.
    Sato, M.; Taniguchi, T.; Hirokawa, T.; Kaneko, C. Tetrahedron Lett. 1995, 36, 6705.CrossRefGoogle Scholar
  41. 41.
    Sato, M.; Hirokawa, T.; Hattori, H.; Toyota, A.; Kaneko, C. Tetrahedron Asymmetry 1994, 5, 975.CrossRefGoogle Scholar
  42. 42.
    Toyota, A.; Uchiyama, M.; Kaneko, C. Tetrahedron 1997, 53, 6327.CrossRefGoogle Scholar
  43. 43.
    Feiring, A. E.; Rozen, S.; Wonchoba, E. R. J. Fluorine Chem. 1998, 89, 31.CrossRefGoogle Scholar
  44. 44.
    Chambers, R. D.; Fox, M. A.; Sanford, G.; Trmcic, J.; Goeta, A. J. Fluorine Chem. 2007, 128, 29.CrossRefGoogle Scholar
  45. 45.
    Storer, R.; Ashton, C. J.; Baxter, A. D.; Han, M. M.; Marr, C. L. P.; Mason, A. M.; Mo, C. L.; Myers, P. L.; Noble, S. A.; Penn, C. R.; Weir, N. G.; Woods, J. M.; Coe, P. L. Nucleosides Nucleotides 1999, 18, 203.CrossRefGoogle Scholar
  46. 46.
    Selig, H.; Lifshitz, C.; Peres, T.; Fischer, J. E.; McGhie, A. R.; Romanow, W. J.; McCauley Jr, J. P.; Smith, A. B., III J. Am. Chem. Soc. 1991, 113, 5475.CrossRefGoogle Scholar
  47. 47.
    Tuinman, A. A.; Gakh, A. A.; Adcock, J. L.; Compton, R. N. J. Am. Chem. Soc. 1993, 115, 5885.CrossRefGoogle Scholar
  48. 48.
    Kniaz, K; Fischer, J. E.; Selig, H.; Vaugham, G. B. M.; Romanow, W. J.; Cox, D. M.; Chowdhury, S. K.; McCauley, J. P.; Strongin, R. M.; Smith, A. B., III J. Am. Chem. Soc. 1993, 115, 6060.CrossRefGoogle Scholar
  49. 49.
    Muramatsu, H.; Kim, Y. A.; Hayashi, T.; Endo, M.; Yonemoto, A.; Arikai H.; Okino, F.; Touhara, H Chem. Commun. 2005, 2002.Google Scholar

Copyright information

© Springer Nature Singapore Pte Ltd. 2018

Authors and Affiliations

  1. 1.School of Chemistry, Tel-Aviv UniversityTel-AvivIsrael