Simple and convenient synthesis of 3,5-bis-(trifluoromethyl)benzylamine via biomimetic 1,3-proton shift reaction

Journal of Fluorine Chemistry

Volumn 127, Issue 7, 2006, Pages 889-893

  Soloshonok, Vadim A ^a   Yasumoto, Manabu ^a  

^a UNIVERSITY OF OKLAHOMA   (United States)

Author keywords

1,3 Proton shift reaction; Biomimetic reductive methodology; Fluorine and compounds; Imines; Operationally convenient conditions

Indexed keywords

EID: 33745200707     PISSN: 00221139     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.jfluchem.2006.03.013     Document Type: Article

References (27)

1. V.A. Soloshonok, V.A. Petrov (Guest Editors) J. Fluor. Chem. 125 (2004) 487-645 (Special Issue).
2. In: Soloshonok V.A. (Ed). ACS Symposium Series #911 (2005), Oxford University Press
3. Cappelli A., Giuliani G., Mohr G.P., Gallelli A., Anzini M., Vomero S., Cupello A., Scarrone S., Matarrese M., Moresco R.M., Fazio F., Finetti F., Morbidelli L., and Ziche M. J. Med. Chem. 47 (2004) 1315-1318
4. Seto S., Tanioka A., Ikeda M., and Izawa S. Bioorg. Med. Chem. 13 (2005) 5717-5732
5. Sulnier M.G., Zimmermann K., Struzynski C.P., Xiaopeng S., Velaparthi U., Wittman M., and Frennwsson D.B. Tetrahedron Lett. 45 (2004) 397-399
6. A. Wada, T. Fujima, S. Sakamoto, Jpn. Kokai Tokkyo Koho JP 03,238,499 (2003).
7. Y. Hamada, K. Umezu, Y. Yoshida, PCT Int. Appl. 02,096,853 (2002).
8. For most recent publications, see
9. Berbasov D.O., Ojemaye I.D., and Soloshonok V.A. J. Fluor. Chem. 125 (2004) 603-607
10. Ohkura H., Berbasov D.O., and Soloshonok V.A. Tetrahedron 59 (2003) 1647-1656
11. Ohkura H., Berbasov D.O., and Soloshonok V.A. Tetrahedron Lett. 44 (2003) 2417-2420
12. Soloshonok V.A., Ohkura H., and Uneyama K. Tetrahedron Lett. 43 (2002) 5449-5452
13. The term "transamination" was coined in the following paper, A.E. Braunshtein, M.G. Kritsman, Biokhimiya (Moscow) 2 (1937) 859-874.
14. Upthagrove A.L., and Nelson W.L. Drug Metabol. Dispos. 29 (2001) 1377-1388
15. Jiang J., Shah H., and DeVita R.J. Org. Lett. 5 (2003) 4101-4103
16. Yuan C., Li S., Xiao J., Cui S., and Wang G. Phosphorus, Sulfur Silicon Relat. Elem. 177 (2002) 1731-1734
17. Yuan C., Li S., and Xiao J. Heteroat. Chem. 11 (2000) 541-545
18. Xiao J., Zhang X., and Yuan C. Heteroat. Chem. 11 (2000) 536-540
19. Soloshonok V.A., and Berbasov D.O. J. Fluor. Chem. 125 (2004) 1757-1763
20. Kanai M., Yasumoto M., Kuriyama Y., Inomiya K., Katsuhara Y., Higashiyama K., and Ishii A. Org. Lett. 5 (2003) 1007-1010
21. Khotkevich A.B., Soloshonok V.A., and Yagupolskii Y.L. Zh. Obshch. Khim. 60 (1990) 1005-1008 (Chem. Abstr. 113: 171274y)
22. Soloshonok V.A., and Ono T. Synlett (1996) 919-921
23. Soloshonok V.A., and Ono T. Tetrahedron 52 (1996) 14701-14712
24. Ono T., Kukhar V.P., and Soloshonok V.A. J. Org. Chem. 61 (1996) 6563-6569
25. Soloshonok V.A., and Ono T. J. Org. Chem. 62 (1997) 3030-3031
26. Soloshonok V.A., Ono T., and Soloshonok I.V. J. Org. Chem. 62 (1997) 7538-7539
27. (p-Methoxy)benzylamine 12 is more than 10 times more expansive than benzylamine.