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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Letter Article

Trifluoroacetylation of Anilines with Ethyl Trifluoropyruvate Mediated by Copper(I) Chloride

Author(s): Jieyu Zhang, Qiumin Ke, Jiaying Chen, Jian Yu* and Guobing Yan*

Volume 16, Issue 11, 2019

Page: [860 - 864] Pages: 5

DOI: 10.2174/1570178616666190311162001

Price: $65

Abstract

A novel copper(I)-mediated trifluoroacetylation of anilines with ethyl trifluoropyruvate as a trifluoroacetylating reagent has been developed. Although this protocol could provide good yields in most cases, the reaction exhibited the obvious electronic and steric effects of substituents. The trace amount of products was only obtained for the substrates with ortho-substituted or electron-deficient groups.

Keywords: Trifluoroacetylation, anilines, ethyl trifluoropyruvate, copper catalysis, cross-coupling, deficient groups.

Graphical Abstract

[1]
Green, T.W.; Wuts, P.G.M. Protective Groups in Organic Synthesis, 4th ed; Wiley-Interscience: New York, 2007.
[2]
Friestad, G.K.; Banerjee, K. Org. Lett., 2009, 11, 1095-1098.
[3]
(a) Schallenberg, E.E.; Calvin, M. J. Am. Chem. Soc., 1955, 77, 2779-2783.
(b) Jr. Forbus, T.R. Taylor, S.L.; Martin. J.C. J. Org. Chem., 1987, 52, 4156-4159.
(c) Bergeron, R.J.; McMains, J.S. J. Org. Chem., 1988, 53, 3108-3111.
(d) Katritzky, A.R.; Yang, B.; Qiu, G.; Zhang, Z. Synthesis, 1999, 55-57.
(e) Katritzky, A.R.; Yang, B.; Semenzin, D. J. Org. Chem., 1997, 62, 726-728.
(f) Delgado, A.; Clardy, J. J. Org. Chem., 1993, 58, 2862-2866.
(g) Kiselyov, A.S.; Harvey, R.G. Tetrahedron Lett., 1995, 36, 4005-4008.
(h) Prashad, M.; Hu, B.; Har, D.; Repič, O.; Blacklock, T.J. Tetrahedron Lett., 2000, 41, 9957-9961.
(i)Gribble, G.W.; Fraser, H.L.; Badenock, J.C. Chem. Commun., 2001, 805-806.
(j)Wynne, J.H.; Lloyd, C.T.; Jensen, S.D.; Boson, S.; Stalick, W.M. Synthesis, 2004, 14, 2277-2282.
(k)Park, C.M.; Kim, S.Y.; Park, W.K.; Park, N.S.; Seong, C.M. Bioorg. Med. Chem. Lett., 2008, 18, 3844-3847.
(l)Ohtaka, J.; Sakamoto, T.; Kikugawa, Y. Tetrahedron Lett., 2009, 50, 1681-1683.
(m)Bovens, S.; Elfringhoff, A.S.; Kaptur, M.; Reinhardt, D.; Schäfers, M.; Lehr, M. J. Med. Chem., 2010, 53, 8298-8308.
(n)Kim, J.G.; Jang, D.O. Tetrahedron Lett., 2010, 51, 683-685.
[4]
Saha, A.; van Heijst, J.; Sakamoto, J.; Schlüter, A.D. Synlett, 2012, 23, 1467-1472.
[5]
(a) Lyle, M.P.A.; Draper, N.D.; Wilson, P.D. Org. Lett., 2005, 7, 901-904.
(b) Nakamura, S.; Hyodo, K.; Nakamura, Y.; Shibata, N.; Torua, T. Adv. Synth. Catal., 2008, 350, 1443-1448.
(c) Nie, J.; Zhang, G.W.; Wang, L.; Zheng, D.H.; Zheng, Y.; Ma, J-A. Eur. J. Org. Chem., 2009, 3145-3149.
(d) Grach, G.; Dinut, A.; Marque, S.; Marrot, J.; Gil, R.; Prim, D. Org. Biomol. Chem., 2011, 9, 497-503.
(e) Han, X.; Liu, B.; Zhou, H-B. Tetrahedron Asymmetry, 2012, 23, 1332-1337.
(f) Han, X.; Ouyang, W.; Liu, B.; Wang, W.; Tien, P.; Wu, S.; Zhou, H-B. Org. Biomol. Chem., 2013, 11, 8463-8475.
[6]
Wu, W.; Tian, Q.; Chen, T.; Weng, Z. Chem.-Eur. J., 2016, 22, 16455-16458.
[7]
Darehkordi, A. Rahmani, F. J. Fluor. Chem., 2016, 190, 41-47.
[8]
López, S.E.; Pérez, Y.; Restrepo, J.; Salazar, J.; Charris, J. J. Fluorine. Chem., 2007, 128, 566-569.
[9]
Guo, H.; Wang, Y.; Du, G.F.; Dai, B.; He, L. Tetrahedron, 2015, 71, 3472-3477.
[10]
Augurusa, A.; Mehta, M.; Perez, M.; Zhu, J.; Stephan, D.W. Chem. Commun., 2016, 52, 12195-12198.
[11]
Holder, J.C.; Goodman, E.D.; Kikushima, K.; Gatti, M.; Marziale, A.N.; Stoltz, B.M. Tetrahedron, 2015, 71, 5781-5792.
[12]
Monzon, G.; Tirotta, I.; Knochel, P. Angew. Chem. Int. Ed., 2012, 51, 10624-10627.
[13]
Salazar, J.; López, S.E.; Rebollo, O. J. Fluorine. Chem., 2003, 124, 111-113.
[14]
Bougrin, K.; Loupy, A.; Petit, A.; Benhida, R.; Fourrey, J-L.; Daoua, B.; Soufiaoui, M. Tetrahedron Lett., 2000, 41, 4875-4879.

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