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α,α-Difluorobenzylamines Deoxofluorination

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Fluorination

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

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Introduction

α,α-Difluorobenzylamines are an important class of “N-CF2R” type deoxofluorination reagents. Among various α,α-difluorobenzylamines with different substitution groups, α,α-difluorobenzyl(dimethyl)amine (DBDA) was first used for the deoxofluorination of simple alcohols and carboxylic acids [1]. However, the deoxofluorination property of DBDA has not been systematically studied, and the thermal stability of DBDA was also not shown. In 2004, N,N-Diethyl-α,α-difluoro(meta-methylbenzyl)amine (DFMBA) was first reported as a deoxofluorination reagent by Hara and coworkers [2]. In the next few years, the deoxofluorination property of DFMBA was well studied. DFMBA is a commercially available colorless liquid with boiling point of 81–83 °C/4 mmHg. Accelerating rate calorimetry analysis (ARC) showed that it is stable at temperatures up to 180 °C and decomposes gradually at 210 °C [3]. However, DFMBA can be destroyed gradually by moisture in air; thus, it must be stored in the...

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References

  1. Dmowski, W.; Kamiński, M. J. Fluorine Chem.1983, 23, 219–228.

    Article  CAS  Google Scholar 

  2. Kobayashi, S.; Yoneda, A.; Fukuhara, T.; Hara, S. Tetrahedron Lett.2004, 45, 1287–1289.

    Article  CAS  Google Scholar 

  3. Yoshimura, T.; Fushimi, N.; Hidaka, T.; Kawai, K. WO 03/020685 A1 2003.

    Google Scholar 

  4. Hasek, W. R.; Smith, W. C.; Engelhardt, V. A. J. Am. Chem. Soc.1960, 82, 543–551.

    Article  CAS  Google Scholar 

  5. (a) Dmowski, W.; Kamiński, M. J. Fluorine Chem.1983, 23, 207–218. (b) Dmowski, W.; Kamiński, M. Pol. J. Chem.1982, 56, 1369–1378.

    Google Scholar 

  6. Furuya, T.; Fukuhara, T.; Hara, S. J. Fluorine Chem.2005, 126, 721–725.

    Article  CAS  Google Scholar 

  7. Fukuhara, T.; Hasegawa, C.; Hara, S. Synthesis2007, 2007, 1528–1534.

    Article  Google Scholar 

  8. Sharts, C. M.; Sheppard, W. A. Org. React.1974, 21, 160.

    Google Scholar 

  9. Lloyd, A. E.; Coe, P. L.; Walker, R. T.; Howarth, O. W. J. Fluorine Chem.1993, 60, 239–250.

    Article  CAS  Google Scholar 

  10. Kobayashi, S.; Yoneda, A.; Fukuhara, T.; Hara, S. Tetrahedron2004, 60, 6923–6930.

    Article  CAS  Google Scholar 

  11. Szarek, W. A.; Grynkiewicz, G.; Doboszewski, B.; Hay, G. W. Chem. Lett.1984, 13, 1751–1754.

    Article  Google Scholar 

  12. Fujimoto, Y.; Iwata, M.; Imakita, N.; Shimoyama, A.; Suda, Y.; Kusumoto, S.; Fukase, K. Tetrahedron Lett.2007,48, 6577–6581.

    Article  CAS  Google Scholar 

  13. Yoneda, A.; Fukuhara, T.; Hara, S. Chem. Commun.2005, 3589–3590.

    Google Scholar 

  14. Ahmed, M. M.; O’Doherty, G. A. Carbohydr. Res.2006, 341, 1505–1521.

    Article  CAS  Google Scholar 

  15. Suwada, M.; Fukuhara, T.; Hara, S. J. Fluorine Chem.2007, 128, 1121–1125.

    Article  CAS  Google Scholar 

  16. Nomoto, T.; Fukuhara, T.; Hara, S. Synlett2006, 2006, 1744–1746.

    Article  Google Scholar 

  17. Wakita, N.; Hara, S. Tetrahedron2010, 66, 7939–7945.

    Article  CAS  Google Scholar 

  18. Hamatani, T.; Matsubara, S.; Matsuda, H.; Schlosser, M. Tetrahedron1988, 44, 2875–2881.

    Article  CAS  Google Scholar 

  19. Tavasli, M.; O’Hagan, D.; Pearson, C.; Petty, M. C. Chem. Commun.2002, 1226–1227.

    Google Scholar 

  20. Yu, H.-W.; Nakano, Y.; Fukuhara, T.; Hara, S. J. Fluorine Chem.2005, 126, 962–966.

    Article  CAS  Google Scholar 

  21. Sano, K.; Fukuhara, T.; Hara, S. J. Fluorine Chem.2009, 130, 708–713.

    Article  CAS  Google Scholar 

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Correspondence to Jinbo Hu .

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Li, L., Hu, J. (2020). α,α-Difluorobenzylamines Deoxofluorination. In: Hu, J., Umemoto, T. (eds) Fluorination. Synthetic Organofluorine Chemistry. Springer, Singapore. https://doi.org/10.1007/978-981-10-3896-9_49

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