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Fluorination pp 1–11Cite as

Chemistry of BrF3 Constructing the CF2, CF3 and CF2H Groups

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

Bromine trifluoride, made directly from Br2 and F2, has been known since the beginning of the twentieth century [1]. However, it was rarely used in organic chemistry mainly because of its violent nature when it comes in contact with water or certain organic solvents. Martin was one of the first organic scientists to use BrF3 successfully as a fluorinating agent for octahedral nonmetallic elements (1) [2] followed by Lemal who used it for the synthesis of hexafluorocyclopentadiene (2) [3]. A few years later, Boguslavskaya and coworkers used it for fluorination of some short chlorinated alkane chains which invariably gave mixtures (e.g., 3 and 4) [4]. Gassen also performed similar chemistry and converted 3-chloropropene into α-fluoroacrylic acid (5) [5] (Fig. 1).

Fig. 1
figure 1

Some early works with BrF3

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References

  1. Labeau, H J. Phys. Chem. 1906, 10, 419.

    Google Scholar 

  2. Michalak, R. S.; Wilson, S. R.; Martin, J. C. (1984) J. Am. Chem. Soc., 106, 7529.

    Article  CAS  Google Scholar 

  3. Soelch, R. R.; Mauer, G. W.; Lemal, D. M. J. Org. Chem. 1985, 50, 5845.

    Article  CAS  Google Scholar 

  4. a) Kartashov, A. V.; Chuvatkin, N. N.; Boguslavskaya, L. S. Zhur. Organich. Khim. 1988, 24, 2522 (Engl. Trans.: Russ. J. Org. Chem. 1989, 2279). b) Kartashov, A. V.; Chuvatkin, N. N.; Boguslavskaya, L. S. ibid 1991, 27, 2522 (Engl. Trans.: Russ. J. Org. Chem. 1992, 2243). c) Kartashov, A. V.; Chuvatkin, N. N.; Boguslavskaya, L. S. ibid, 1989, 25, 2452.

    Google Scholar 

  5. Gassen, K. R.; Bielefeldt, D.; Marhold, A.; Andres, P. J. Fluorine Chem. 1991, 55, 149.

    Article  CAS  Google Scholar 

  6. (a) Rozov, L. A.; Huang, C. G.; Halpern, D. F.; Vernice, G. G. US Patent 5,283,372, 1994. (b) Rozov, L. A.; Huang, C. G.; Halpern, D. F.; Vernice, G. G.; Ramig, K. Tetrahedron Asymm. 1997, 8, 3023. (c) Ramig, K. Synthesis 2002, 2627.

    Google Scholar 

  7. Ruzicka, J. A.; Hardy, J. B.; Baker, M. T. J. Fluorine. Chem. 1995, 75, 191.

    Article  CAS  Google Scholar 

  8. Cohen, O.; Sasson, R.; Rozen, S. J. Fluorine Chem. 2006, 127, 433.

    Article  CAS  Google Scholar 

  9. Feiring, A. E.; Rozen, S.. U. S. Patent #5830962 (1998).

    Google Scholar 

  10. Shishimi, T., Hara, S. J. Fluorine Chem. 2013, 145, 128.

    Article  CAS  Google Scholar 

  11. Hagooly, A.; Ben-David, I.; Rozen, S. J. Org. Chem. 2002, 67, 8430.

    Article  CAS  Google Scholar 

  12. Hagooly, Y.; Rozen, S. Org. Lett. 2012, 14, 1114.

    Article  CAS  Google Scholar 

  13. I. Ben-David, D. Rechavi, E. Mishani, S. Rozen, J. Fluorine Chem. 1999, 97, 75.

    Article  CAS  Google Scholar 

  14. Hagooly, Y.; Sasson, R.; Welch, M. J.; Rozen, S. Eur. J. Org. Chem., 2008, 19, 2875.

    Article  Google Scholar 

  15. Hagooly, Y.; Cohen, O.; Rozen, S. Tetrahedron Lett. 2009, 50, 392.

    Article  CAS  Google Scholar 

  16. Hagooly, A; Rozen, S. Chem. Commun. 2004, 594.

    Google Scholar 

  17. Hagooly, A; Rozen, S. J. Org. Chem. 2004, 69, 7241.

    Article  CAS  Google Scholar 

  18. Rozen, S.; Mishani E. J. Chem. Soc. Chem. Commun. 1994, 2081.

    Google Scholar 

  19. Cohen, O.; Mishani, E.; Rozen, S. Tetrahedron 2010, 65, 3579.

    Article  Google Scholar 

  20. Hagooly, A.; Sasson, R.; Rozen, S. J. Org. Chem. 2003, 68, 8287.

    Article  CAS  Google Scholar 

  21. Sasson, R.; Rozen, S. Tetrahedron 2005, 61, 1083.

    Article  CAS  Google Scholar 

  22. Hagooly, Y.; Gatenyo, J.; Hagooly, A.; Rozen, S. J. Org. Chem. 2009, 74, 8578.

    Article  CAS  Google Scholar 

  23. Rozen, S.; Mishani, E.; Bar-Haim, A. J. Org. Chem. 1994, 59, 2918.

    Article  CAS  Google Scholar 

  24. Sasson, R.; Hagooly, A.; Rozen, S. Org. Lett. 2003, 5, 769.

    Article  CAS  Google Scholar 

  25. Shishimi, T.; Hara, S. J. Fluorine Chem. 2014, 168, 55.

    Article  CAS  Google Scholar 

  26. Hagooly, A.; Rozen, S. J. Fluorine Chem. 2005, 126, 1239.

    Article  CAS  Google Scholar 

  27. Hagooly, A.; Rozen, S. J. Org. Chem. 2004, 69, 8786.

    Article  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  29. Rozen, S.; Mishani E. J. Chem. Soc. Chem. Commun. 1993, 1761.

    Google Scholar 

  30. Hagooly, Y.; Welch, M. J.; Rozen, S. Org. Biomol. Chem. 2011, 9, 902.

    Article  CAS  Google Scholar 

  31. Y. Hagooly, S. Rozen, J. Org. Chem., 2008, 73, 6780.

    Article  CAS  Google Scholar 

  32. Rozen S.; Lerman, O. J. Org. Chem. 1993, 58, 239.

    Article  CAS  Google Scholar 

  33. Sasson, R.; Rozen, S. Org. Lett. 2005, 7, 2177.

    Article  CAS  Google Scholar 

  34. Matthews, D. P.; Whitten, J. P.; McCarthy, J. R. J. Org. Chem. 1986, 51, 3228.

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. Organic Chemistry, School of Chemistry, Tel-Aviv University, Tel-Aviv, 69978, Israel

    Shlomo Rozen

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  1. Shlomo Rozen
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Correspondence to Shlomo Rozen .

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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

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Rozen, S. (2018). Chemistry of BrF3 Constructing the CF2, CF3 and CF2H Groups. In: Hu, J., Umemoto, T. (eds) Fluorination. Synthetic Organofluorine Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-10-1855-8_32-1

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  • DOI: https://doi.org/10.1007/978-981-10-1855-8_32-1

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  • 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

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