Abstract
Amines are invaluable precursors and necessary chemical components in industrial settings as well as pharmaceutical industries, making methods for efficient formation of C-N bonds a vital chemical process. Of these methods, the hydroamination of alkenes and alkynes, specifically the addition of an N-H bond across a carbon-carbon π-bond, is especially relevant. The hydroamination reaction is theoretically 100% atom-economical, making it a desirable synthetic route for the formation of C-N bonds. Common synthetic methods for amines are cumbersome and require multiple steps that produce waste products. However, the hydroamination reaction itself has a large negative entropy, requiring the assistance of a catalyst to promote the reaction. As such, current research focuses on the development of organometallic catalysts that can increase the efficacy of hydroamination reactions. Herein, research towards the development of an efficient catalyst for intramolecular hydroamination of alkene is reviewed.
Similar content being viewed by others
References
Berndt, E.R., Health Affairs, 2001, vol. 20, p. 100.
Dugger, R.W., Ragan, J.A., and Ripin, D.H.B., Org. Process Res. Dev., 2005, vol. 9, p. 253.
Gübitz, G. and Schmid, M.G., Biopharm. Drug Dispos., 2001, vol. 22, p. 291.
Barbosa-Filho, J.M., Piuvezam, M.R., Moura, M.D., Silva, M.S., Lima, K.V.B., da-Cunha, E.V.L., Fechine, I.M., and Takemura, O.S., Revista Brasileira de Farmacognosia, 2006, vol. 16, p. 109.
Newman, D.J., Cragg, G.M., and Snader, K.M., J. Nat. Prod., 2003, vol. 66, p. 1022.
Mander, L.N. and McLachlan, M.M., J. Am. Chem. Soc., 2003, vol. 125, p. 2400.
Yang, P. and Zhou, Y. The enantioselective total synthesis of alkaloid (-)-galipeine, Tetrahedron: Asymmetry, 2004, vol. 15, p. 1145.
Larock, R.C., Comprehensive Organic Transformations: A Guide to Functional Group Preparations, USA: John Wiley and Sons, Inc., 1999, p. 2583.
Salvatore, R.N., Yoon, C.H., and Jung, K.W., Tetrahedron, 2001, vol. 57, p. 7785.
Ram, S. and Ehrenkaufer, R.E., Tetrahedron Lett., 1984, vol. 25, p. 3415.
Amundsen, L.H. and Nelson, L.S., J. Am. Chem. Soc., 1951, vol. 73, p. 242.
Micovic, V. and Mihailovic, M., J. Org. Chem., 1953, vol. 18, p. 1190.
Abdel-Magid, A., Carson, K.G., Harris, B.D., Maryanoff, C.A., and Shah, R.D., J. Org. Chem., 1996, vol. 61, p. 3849.
Apodaca, R. and Xiao, W., Org. Lett., 2001, vol. 3, p. 1745.
Raspoet, G., Nguyen, M.T., McGarraghy, M., and Hegarty, A.F., J. Org. Chem., 1998, vol. 63, p. 6867.
Saunders, J.H. and Slocombe, R.J., Chem. Rev., 1948, vol. 43, p. 203.
Beller, M., Trauthwein, H., Eichberger, M., Breindl, C., Herwig, J., Müller, T.E., and Thiel, O.R., Chemistry A European Journal, 1999, vol. 5, p. 1306.
Senn, H.M., Blochl, P.E., and Togni, A., J. Am. Chem. Soc., 2000, vol. 122, p. 4098.
MacDonald, M.J., Schipper, D.J., Ng, P.J., Moran, J., and Beauchemin, A.M., J. Am. Chem. Soc., 2011, vol. 133, p. 20100.
Severin, R. and Doye, S., Chem. Soc. Rev., 2007, vol. 36, p. 1407.
Müller, T.E., Hultzsch, K.C., Yus, M., Foubelo, F., and Tada, M., Chem. Rev., 2008, vol. 108, p. 3795.
Fujita, H., Tokuda, M., Nitta, M., and Suginome, H., Tetrahedron Lett., 1992, vol. 33, p. 6359.
Gagne, M.R., Stern, C.L., and Marks, T.J., J. Am. Chem. Soc., 1992, vol. 114, p. 275.
Hong, S. and Marks, T.J., Acc. Chem. Res., 2004, vol. 37, p. 673.
Li, Y. and Marks, T.J., J. Am. Chem. Soc., 1996, vol. 118, p. 9295.
Crimmin, M.R., Casely, I.J., and Hill, M.S., J. Am. Chem. Soc., 2005, vol. 127, p. 2042.
Leitch, D.C., Payne, P.R., Dunbar, C.R., and Schafer, L.L., J. Am. Chem. Soc., 2009, vol. 131, p. 18246.
Reznichenko, A.L. and Hultzsch, K.C., Organometallics, 2010, vol. 29, p. 24.
Thomson, R.K., Bexrud, J.A., and Schafer, L.L., Organometallics, 2006, vol. 25, p. 4069.
Hesp, K.D., Tobisch, S., and Stradiotto, M., J. Am. Chem. Soc., 2010, vol. 132, p. 413.
Julian, L.D. and Hartwig, J.F., J. Am. Chem. Soc., 2010, vol. 132, p. 13813.
Liu, Z., Yamamichi, H., Madrahimov, S.T., and Hartwig, J.F., J. Am. Chem. Soc., 2011, vol. 133, p. 2772.
Takemiya, A. and Hartwig, J.F., J. Am. Chem. Soc., 2006, vol. 128, p. 6042.
Utsunomiya, M., Kuwano, R., Kawatsura, M., and Hartwig, J.F., J. Am. Chem. Soc., 2003, vol. 125, p. 5608.
Taylor, J.G., Whittall, N., and Hii, K.K., Org. Lett., 2006, vol. 8, p. 3561.
Roveda, J., Clavette, C., Hunt, A.D., Gorelsky, S.I., Whipp, C.J., and Beauchemin, A.M., J. Am. Chem. Soc., 2009, vol. 131, p. 8740.
Layer, R.W., Chem. Rev., 1963, vol. 63, p. 489.
Craig, N.L., Cohen-Fix, O., Green, R., Greider, C.W., Storz, G., and Wolberger, C., Molecular biology: principles of genome function, in The Chemical Basis of Life, New York: Oxford University Press, 2010, p. 83.
Arredondo, V.M., McDonald, F.E., and Marks, T.J., Organometallics, 1999, vol. 18, p. 1949.
Arredondo, V.M., Tian, S., McDonald, F.E., and Marks, T.J., J. Am. Chem. Soc., 1999, vol. 121, p. 3633.
Dang, Q., Liu, Y., and Erion, M.D., J. Am. Chem. Soc., 1999, vol. 121, p. 5833.
Ryu, J., Marks, T.J., and McDonald, F.E., J. Org. Chem., 2004, vol. 69, p. 1038.
Mauermann, H., Swepston, P.N., and Marks, T.J., Organometallics, 1985, vol. 4, p. 200.
Gagne, M.R., Nolan, S.P., and Marks, T.J., Organometallics, 1990, vol. 9, 1716.
Giardello, M.A., Conticello, V.P., Brard, L., Sabat, M., Rheingold, A.L., Stern, C.L., and Marks, T.J., J. Am. Chem. Soc., 1994, vol. 116, p. 10212.
Hong, S., Tian, S., Metz, M.V., and Marks, T.J., J. Am. Chem. Soc., 2003, vol. 125, p. 14768.
Riegert, D., Collin, J., Meddour, A., Schulz, E., and Trifonov, A., J. Org. Chem., 2006, vol. 71, p. 2514.
Hong, S. and Marks, T.J., J. Am. Chem. Soc., 2002, vol. 124, p. 7886.
Hong, S., Kawaoka, A.M., and Marks, T.J., J. Am. Chem. Soc., 2003, vol. 125, p. 15878.
Bruno, J.W., Marks, T.J., and Morss, L.R., J. Am. Chem. Soc., 1983, vol. 105, p. 6824.
Douglass, M.R., Ogasawara, M., Hong, S., Metz, M.V., and Marks, T.J., Organometallics, 2002, vol. 21, p. 283.
Beesley, R.M., Ingold, C.K., and Thorpe, J.F., J. Chem. Soc. Trans., 1915, vol. 107, p. 1080.
Lauterwasser, F., Hayes, P.G., Bräase, S., Piers, W.E., and Schafer, L.L., Organometallics, 2004, vol. 23, p. 2234.
Bexrud, J.A., Beard, J.D., Leitch, D.C., and Schafer, L.L., Org. Lett., 2005, vol. 7, p. 1959.
Hoover, J.M., Petersen, J.R., Pikul, J.H., and Johnson, A.R., Organometallics, 2004, vol. 23, p. 4614.
Bauer, E.B., Andavan, G.T.S., Hollis, T.K., Rubio, R.J., Cho, J., Kuchenbeiser, G.R., Helgert, T.R., Letko, C.S., and Tham, F.S., Org. Lett., 2008, vol. 10, p. 1175.
Ohmiya, H., Moriya, T., and Sawamura, M., Org. Lett., 2009, vol. 11, p. 2145.
Burling, S., Field, L.D., and Messerle, B.A., Organometallics, 2000, vol. 19, p. 87.
Hartung, C.G., Tillack, A., Trauthwein, H., and Beller, M., J. Org. Chem., 2001, vol. 66, p. 6339.
Burling, S., Field, L.D., Messerle, B.A., and Turner, P., Organometallics, 2004, vol. 23, p. 1714.
Burling, S., Field, L.D., Messerle, B.A., and Rumble, S.L., Organometallics, 2007, vol. 26, p. 4335.
Liu, Z. and Hartwig, J.F., J. Am. Chem. Soc., 2008, vol. 130, p. 1570.
Bender, C.F. and Widenhoefer, R.A., J. Am. Chem. Soc., 2005, vol. 127, p. 1070.
Bender, C.F., Hudson, W.B., and Widenhoefer, R.A., Organometallics, 2008, vol. 27, p. 2356.
Michael, F.E. and Cochran, B.M., J. Am. Chem. Soc., 2006, vol. 128, p. 4246.
Toyooka, N., Fukutome, A., Nemoto, H., Daly, J.W., Spande, T.F., Garraffo, H.M., and Kaneko, T., Org. Lett., 2002, vol. 4, p. 1715.
Yu, J., Wearing, X.Z., and Cook, J.M., Tetrahedron Lett., 2003, vol. 44, p. 543.
Novak, B.H., Hudlicky, T., Reed, J.W., Mulzer, J., and Trauner, D., Curr. Org. Chem., 2000, vol. 4, p. 343.
Voet, D., Voet, J.G., and Pratt, C.W., Fundamentals of biochemistry: life at the molecular level, hoboken, in Amino Acid Metabolism, NJ: John Wiley and Sons, 2008, p. 732.
Author information
Authors and Affiliations
Corresponding author
Additional information
The article is published in the original.
Rights and permissions
About this article
Cite this article
Patton, D.A., Cremeens, M.E. Organometallic catalysts for intramolecular hydroamination of alkenes. Ref. J. Chem. 4, 1–20 (2014). https://doi.org/10.1134/S207997801304002X
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S207997801304002X