Letters in Organic Chemistry

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

DOI: 10.2174/1570178616666190311162001

DownloadDownload PDF Flyer Cite As
Trifluoroacetylation of Anilines with Ethyl Trifluoropyruvate Mediated by Copper(I) Chloride

Page: [860 - 864] Pages: 5

  • * (Excluding Mailing and Handling)

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.