Artículos de revistas
Hydroamination Reactions By Metal Triflates: Brønsted Acid Vs. Metal Catalysis?
Registro en:
Dalton Transactions. , v. 39, n. 5, p. 1171 - 1175, 2010.
14779226
10.1039/b918970j
2-s2.0-76749171787
Autor
Taylor J.G.
Adrio L.A.
Hii K.K.
Institución
Resumen
Catalytic hydroamination reactions involving the addition of carboxamides (X = CO), carbamates (X = CO2) and sulfonamides (X = SO2) to unactivated CC bonds are briefly reviewed. Development in this field of catalytic research is briefly charted, followed by a discussion of possible mechanisms, including arguments to support the operation of both metal and Brønsted acid catalysis in these systems. Future developments in the area are summarised. © The Royal Society of Chemistry 2010. 39 5 1171 1175 Müller, T.E., Hultzsch, K.C., Yus, M., Foubelo, F., Tada, M., (2008) Chem. Rev., 108, p. 3795 Constable, D.J.C., Dunn, P.J., Hayler, J.D., Humphrey, G.R., Leazer, J.L., Linderman, R.J., Lorenz, K., Zhang, T.Y., (2007) Green Chem., 9, p. 411 Ranu, B.C., Banerjee, S., (2007) Tetrahedron Lett., 48, p. 141. , For example, see Kumar, R., Chaudhary, P., Nimesh, S., Chandra, R., (2006) Green Chem., 8, p. 356 Dzhemilev, U., Tolstikov, G., Khusnutdinov, R., (2009) Russ. J. Org. Chem., 45, p. 957 Quinet, C., Jourdain, P., Hermans, C., Atest, A., Lucas, I., Marko, I.E., (2008) Tetrahedron, 64, p. 1077. , See for example Horrillo-Martinez, P., Hultzsch, K.C., Gil, A., Branchadell, V., (2007) Eur. J. Org. Chem., p. 3311 Crimmin, M.R., Arrowsmith, M., Barrett, A.G.M., Casely, I.J., Hill, M.S., Procopiou, P.A., (2009) J. Am. Chem. Soc., 131, p. 9670 Hong, S., Marks, T.J., (2004) Acc. Chem. Res., 37, p. 673 Walsh, P.J., Baranger, A.M., Bergman, R.G., (1992) J. Am. Chem. Soc., 114, p. 1708 Müller, C., Koch, R., Doye, S., (2008) Chem.-Eur. J., 14, p. 10430 Beller, M., Trauthwein, H., Eichberger, M., Breindl, C., Herwig, J., Müller, T.E., Thiel, O.R., (1999) Chem.-Eur. J., 5, p. 1306 Rodriguez-Zubiri, M., Anguille, S., Brunet, J.J., (2007) J. Mol. Catal. A: Chem., 271, p. 145 Bäckvall, J.E., Åkermark, B., Ljunggren, S.O., (1979) J. Am. Chem. Soc., 101, p. 2411 Hahn, C., (2004) Chem.-Eur. J., 10, p. 5888. , See for example Motta, A., Fragala, I.L., Marks, T.J., (2006) Organometallics, 25, p. 5533 Tobisch, S., (2008) Chem.-Eur. J., 14, p. 8590 Aillaud, I., Collin, J., Hannedouche, J., Schulz, E., (2007) Dalton Trans., p. 5105 Qian, H., Widenhoefer, R.A., (2005) Org. Lett., 7, p. 2635 Karshtedt, D., Bell, A.T., Tilley, T.D., (2005) J. Am. Chem. Soc., 127, p. 12640 Zhang, J., Yang, C., He, C., (2006) J. Am. Chem. Soc., 128, p. 1798 Brouwer, C., He, C., (2006) Angew. Chem., Int. Ed., 45, p. 1744 Giner, X., Najera, C., (2008) Org. Lett., 10, p. 2919 Taylor, J.G., Whittall, N., Hii, K.K., (2005) Chem. Commun., p. 5103 Taylor, J.G., Whittall, N., Hii, K.K., (2006) Org. Lett., 8, p. 3561 Dias, H.V.R., Wu, J., (2008) Eur. J. Inorg. Chem., p. 509. , For a discussion of ethylene complexes ofCu(i), Ag(i) and Au(i), see McBee, J.L., Bell, A.T., Tilley, T.D., (2008) J. Am. Chem. Soc., 130, p. 16562 Cheng, X.J., Xia, Y.Z., Wei, H., Xu, B., Zhang, C.G., Li, Y.H., Qian, G.M., Li, W., (2008) Eur. J. Org. Chem., p. 1929 Rosenfeld, D.C., Shekhar, S., Takemiya, A., Utsunomiya, M., Hartwig, J.F., (2006) Org. Lett., 8, p. 4179 Li, Z., Zhang, J., Brouwer, C., Yang, C.-G., Reich, N.W., He, C., (2006) Org. Lett., 8, p. 4175 Wabnitz, T.C., Yu, J.Q., Spencer, J.B., (2004) Chem.-Eur. J., 10, p. 484 Taylor, J.G., (2008), PhD Thesis, Imperial College LondonHuang, J.M., Wong, C.M., Xu, F.X., Loh, T.P., (2007) Tetrahedron Lett., 48, p. 3375 Michaux, J., Terrasson, V., Marque, S., Wehbe, J., Prim, D., Campagne, J.M., (2007) Eur. J. Org. Chem., p. 2601 Motokura, K., Nakagiri, N., Mori, K., Mizugaki, T., Ebitani, K., Jitsukawa, K., Kaneda, K., (2006) Org. Lett., 8, p. 4617 Yang, L., Xu, L.W., Xia, C.G., (2008) Tetrahedron Lett., 49, p. 2882 Kovacs, G., Ujaque, G., Lledos, A., (2008) J. Am. Chem. Soc., 130, p. 853 Dorta, R., Egli, P., Zurcher, F., Togni, A., (1997) J. Am. Chem. Soc., 119, p. 10857 Hartwig, J.F., (2004) Pure Appl. Chem., 76, p. 507. , These were shown to proceed via allylpalladium(ii) intermediates, see, and references therein Johns, A.M., Sakai, N., Ridder, A., Hartwig, J.F., (2006) J. Am. Chem. Soc., 128, p. 9306 Zhang, Z., Lee, S.D., Widenhoefer, R.A., (2009) J. Am. Chem. Soc., 131, p. 5372 Anastas, P., Warner, J., (1998) Green Chemistry: Theory and Practice, , Oxford University Press, New York