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Economical and Practical Strategies for Synthesis of a-Trifluoromethylated Amines
Corresponding Author(s) : C.J. Jiang
Asian Journal of Chemistry,
Vol. 27 No. 7 (2015): Vol 27 Issue 7, 2015
Abstract
A powerful approach to synthesize a-trifluoromethylated amines has been developed. The method is operationally simple, broad in substrate scope and amenable to scale-up using trifluoroacetic anhydride. Meanwhile, the strategy not only provided a versatile approach to synthesize a-trifluoromethylated amines but also provides a new method for exploring the new reactivity of trifluoroacetic anhydride.
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- S. Purser, P.R. Moore, S. Swallow and V. Gouverneur, Chem. Soc. Rev., 37, 320 (2008); doi:10.1039/b610213c.
- Y. Gong, K. Kato and H. Kimoto, Bull. Chem. Soc. Jpn., 75, 2637 (2002); doi:10.1246/bcsj.75.2637.
- G.L. Grunewald, J. Lu, K.R. Criscione and C.O. Okoro, Bioorg. Med. Chem. Lett., 15, 5319 (2005); doi:10.1016/j.bmcl.2005.08.033.
- Z.J. Liu and J.T. Liu, Chem. Commun., 41, 5233 (2008); doi:10.1039/b810459j.
- C. Philippe, T. Milcent, T. Nguyen Thi Ngoc, B. Crousse and D. Bonnet-Delpon, Eur. J. Org. Chem., 5215 (2009); doi:10.1002/ejoc.200900578.
- K. Funabiki, M. Nagamori, M. Matsui and D. Enders, Synthesis, 2585 (2002); doi:10.1055/s-2002-35631.
- F. Gosselin, P.D. O’Shea, S. Roy, R.A. Reamer, C. Chen and R.P. Volante, Org. Lett., 7, 355 (2005); doi:10.1021/ol047431x.
- A. Deutsch, H. Glas, A. Hoffmann-Röder and C. Deutsch, RSC Adv., 4, 9288 (2014); doi:10.1039/c3ra47708h.
- M. Liu, J. Li, X. Xiao, Y. Xie and Y. Shi, Chem. Commun., 49, 1404 (2013); doi:10.1039/c2cc37423d.
- Y. Yokoyama and K. Mochida, Tetrahedron Lett., 38, 3443 (1997); doi:10.1016/S0040-4039(97)00641-2.
- Y. Xu and W.R. Dolbier, J. Org. Chem., 65, 2134 (2000); doi:10.1021/jo991750y.
- G.K.S. Prakash and M. Mandal, J. Fluor. Chem., 112, 123 (2001); doi:10.1016/S0022-1139(01)00477-8.
- I. Durán, A. Parrilla, J. Feixas and A. Guerrero, Bioorg. Med. Chem. Lett., 3, 2593 (1993); doi:10.1016/S0960-894X(01)80722-8.
- G.L. Grunewald, T.M. Caldwell, Q. Li and K.R. Criscione, J. Med. Chem., 42, 3315 (1999); doi:10.1021/jm980734a.
References
S. Purser, P.R. Moore, S. Swallow and V. Gouverneur, Chem. Soc. Rev., 37, 320 (2008); doi:10.1039/b610213c.
Y. Gong, K. Kato and H. Kimoto, Bull. Chem. Soc. Jpn., 75, 2637 (2002); doi:10.1246/bcsj.75.2637.
G.L. Grunewald, J. Lu, K.R. Criscione and C.O. Okoro, Bioorg. Med. Chem. Lett., 15, 5319 (2005); doi:10.1016/j.bmcl.2005.08.033.
Z.J. Liu and J.T. Liu, Chem. Commun., 41, 5233 (2008); doi:10.1039/b810459j.
C. Philippe, T. Milcent, T. Nguyen Thi Ngoc, B. Crousse and D. Bonnet-Delpon, Eur. J. Org. Chem., 5215 (2009); doi:10.1002/ejoc.200900578.
K. Funabiki, M. Nagamori, M. Matsui and D. Enders, Synthesis, 2585 (2002); doi:10.1055/s-2002-35631.
F. Gosselin, P.D. O’Shea, S. Roy, R.A. Reamer, C. Chen and R.P. Volante, Org. Lett., 7, 355 (2005); doi:10.1021/ol047431x.
A. Deutsch, H. Glas, A. Hoffmann-Röder and C. Deutsch, RSC Adv., 4, 9288 (2014); doi:10.1039/c3ra47708h.
M. Liu, J. Li, X. Xiao, Y. Xie and Y. Shi, Chem. Commun., 49, 1404 (2013); doi:10.1039/c2cc37423d.
Y. Yokoyama and K. Mochida, Tetrahedron Lett., 38, 3443 (1997); doi:10.1016/S0040-4039(97)00641-2.
Y. Xu and W.R. Dolbier, J. Org. Chem., 65, 2134 (2000); doi:10.1021/jo991750y.
G.K.S. Prakash and M. Mandal, J. Fluor. Chem., 112, 123 (2001); doi:10.1016/S0022-1139(01)00477-8.
I. Durán, A. Parrilla, J. Feixas and A. Guerrero, Bioorg. Med. Chem. Lett., 3, 2593 (1993); doi:10.1016/S0960-894X(01)80722-8.
G.L. Grunewald, T.M. Caldwell, Q. Li and K.R. Criscione, J. Med. Chem., 42, 3315 (1999); doi:10.1021/jm980734a.