The chapter will focus on the tools available for performing a selective replacement of a hydrogen by a metal in organic substrates. In addition some applications to the synthesis of valuable building blocks or target compounds using simple and selective strategies with alkali metals will be also presented.
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References
Clayden, J. Organolithiums: Selectivity for Synthesis. Pergamon Press, Oxford, 2002, Vol. 23.
Hodgson, D. M. (ed.) Organolithiums in Enantioselective Synthesis. Springer, Berlin, 2003, Vol. 5.
Mordini, A. and Valacchi, M. In Science of Synthesis, Majewski, M. S. and Trost, B. M. (eds.), Vol. V. Georg Thieme Verlag, Stuttgart/New York, 2006, Vol. 8b, pp. 1437–1474.
Mordini, A. In Comprehensive Organometallic Chemistry III, Knochel, P. V. E. C., R. H. and Mingos, D. M. P. (eds.), Elsevier, Oxford, 2007, Vol. 9, p. 3–30.
Schlosser, M. In Organometallics in Synthesis. A Manual. Schlosser, M. (ed.), Wiley, London, 1994.
Schlosser, M. In Organometallics in Synthesis. A Manual. 2nd ed., Schlosser, M. (ed.), Wiley, Chichester, 2002.
Schlosser, M. Angew. Chem. Int. Ed. Engl. 2005, 44, 376–393.
Snieckus, V. Chem. Rev. 1990, 90, 879.
Beak, P. and Meyers, A. Acc. Chem. Res. 1986, 19, 356.
Hoppe, D. and Hense, T. Angew. Chem., Int. Ed. Engl. 1997, 36, 2282.
Whistler, M. C., MacNeil, S., Snieckus, V., and Beak, P. Angew. Chem. Int. Ed. Engl. 2004, 43, 2206–2225.
Hoppe, D., Hintze, F., and Tebben, P. Angew. Chem. Int. Ed. Engl. 1990, 29, 1422–1424.
Beak, P., Basu, A., Gallagher, D. J., and Park, Y. S.; Thayumanavan, S. Acc. Chem. Res. 1996, 29, 552.
Nozaki, H., Aratani, T., Toraya, T., and Noyori, R. Tetrahedron 1971, 27, 905–913.
Marsch, M., Harms, K., Zschage, O., Hoppe, D., and Boche, G. Angew. Chem., Int. Ed. Engl. 1991, 30, 321–323.
Hoppe, D., Marr, F., and Bruggemann, M. In Organolithiums in Enantioselective Synthesis. Hodgson, D. M. (ed.), Springer, Berlin, 2003.
Beak, P., Johnson, T. A., Kim, D. D., and Lim, S. H. In Organolithiums in Enantioselective Synthesis, Hodgson, D. M. (ed.), Springer, Berlin, 2003, p. 139–176.
Beak, P., Anderson, D. R., Curtis, M. D., Laumer, J. M., Pippel, D. J., and Weisenburger, G. A. Acc. Chem. Res. 2000, 33, 715–727.
Dixon, A. J., McGrath, M. J., O’Brien, P., Holle, S., and Furstner, A. Organic Synthesis 2006, 83, 141.
O’Brien, P., Wilberg, K. B., Bailey, W. F., Hermet, J.-P. R., and McGrath, M. J. J. Am. Chem. Soc. 2004, 126, 15480.
McGrath, M. J. and O’Brien, P. J. Am. Chem. Soc. 2005, 127, 16378.
McGrath, M. J., Bilke, J. L., and O’Brien, P. Chem. Commun. 2006, 2607.
Wittig, G., Pockels, O., Dröge, H. Ber. Dtsch. Chem. Ges. A 1938, 71, 1903.
Gilman, H. and Bebb, R. J. Am. Chem. Soc. 1939, 61, 109.
Beak, P. and Reitz, D. B. Chem. Rev. 1978, 78, 275.
Meyers, A. Tetrahedron 1992, 48, 2589–2612.
Gilman, H. and Bebb, R. J. Am. Chem. Soc. 19389, 61, 109.
Mongin, F. and Quéguiner, G. Tetrahedron 2001, 57, 4059.
Turck, A., Plé, N., Mongin, F., and Quéguiner, G. Tetrahedron 2001, 57, 4489.
Gros, P. and Fort, Y. Eur. J. Org. Chem. 2002, 3375.
Schlosser, M. J. Organomet. Chem. 1967, 8, 9.
Schlosser, M. Pure Appl. Chem. 1988, 60, 1627.
Schlosser, M. In Modern Synthetic Methods, Scheffold, R. (ed.), Verlag Helvetica Chimica Acta, Basel, 1992, Vol. 6, p. 227.
Schlosser, M., Desponds, O., Lehmann, R., Moret, E., and Rauchschwalbe, G. Tetrahedron 1993, 49, 10175.
Mordini, A. In Advances in Carbanion Chemistry, Snieckus, V. (ed.), Jai Press, Greenwich, CT, 1992, Vol. 1, p. 1.
Mordini, A. In Comprehensive Organometallic Chemistry II. Snieckus, V. V. E. (ed.), Pergamon Press, Oxford, 1995, Vol. 11, p. 93.
Mordini, A., BenRayana, E., Margot, C., and Schlosser, M. Tetrahedron 1990, 46, 2411.
Mordini, A., Russo, F., Valacchi, M., Zani, L., Degl’Innocenti, A., and Reginato, G. Tetrahedron 2002, 58, 7153–7163.
Schlosser, M. and Hartmann, J. J. Am. Chem. Soc. 1976, 98, 4674.
Hartmann, J., Muthukrishnan, R., and Schlosser, M. Helv. Chim. Acta 1974, 57, 2261.
Schlosser, M. and Hartmann, J. Angew. Chem. Int. Ed. Engl. 1973, 12, 508.
Giner, J. L., Margot, C., and Djerassi, C. J. Org. Chem. 1989, 54, 2117.
Desponds, O., Franzini, L., and Schlosser, M. Synthesis 1997, 150.
Hartmann, J. and Schlosser, M. Synthesis 1975, 328.
Rauchschwalbe, G. and Schlosser, M. Helv. Chim. Acta 1975, 58, 1094.
Schlosser, M. and Zhong, G.-F. Tetrahedron Lett. 1993, 34, 5441.
Schlosser, M. and Kotthaus, M. Eur. J. Org. Chem. 1999, 459.
Thompson, T. B. and Ford, W. T. J. Am. Chem. Soc. 1979, 101, 5459.
Schlosser, M. Hartmann, J., and David, V. Helv. Chim. Acta 1974, 57, 1567.
Franzini, L., Moret, E., and Schlosser, M. Chem. Ber. 1997, 130, 83.
Young, S., Coblens, K. E., and Ganem, B. Tetrahedron Lett. 1981, 22, 4887.
Morton, A. A. J. Am. Chem. Soc. 1947, 69, 969.
Maggi, R. and Schlosser, M. J. Org. Chem. 1996, 61, 5430.
Mongin, F., Maggi, R., and Schlosser, M. Chimia 1996, 50, 650.
Katsoulos, G., Takagishi, S., and Schlosser, M. Synlett 1991, 731.
Takagishi, S. and Schlosser, M. Synlett 1991, 119.
Schlosser, M. and Geneste, H. Chem. Eur. J. 1998, 4, 1969.
Margot, C. and Schlosser, M. Tetrahedron 1985, 26, 1035.
Erden, I. In Comprehensive Heterocyclic Chemistry II, Padwa, A. (ed.), Pergamon Press, Oxford, 1996, Vol. 1A, p. 97 e 145.
Pearson, W. H., Lian, B. W. and Bergmeier, S. C. In Comprehensive Heterocyclic Chemistry II, Padwa, A. (ed.), Pergamon Press, Oxford, 1996, Vol. 1A, p. 1.
McCoull, W. and Davis, F. A. Synthesis 2000, 1347–1365.
Aziridines and Epoxides in Organic Synthesis, Yudin, A. K. (ed.), Wiley-VCH, Weinheim, 2006.
Satoh, T. Chem. Rev. 1996, 96, 3303.
Florio, S. E. Tetrahedron, issue on Oxiranyl and Aziridynil Anions as Reactive Intermediates in Synthetic Organic Chemistry 2003, 59, 9683–9864.
Crandall, J. K. and Apparu, M. Org. React. 1983, 29, 345.
Thummel, R. P. and Rickborn, B. J. Am. Chem. Soc. 1970, 92, 2064.
Morgan, K. M., and Gronert, S. J. Org. Chem. 2000, 65, 1461.
Morgan, K. M. and Gajewski, J. J. J. Org. Chem. 1996, 61, 820.
Sodergren, M. J., Bertilsson, S. K., and Andersson, P. G. J. Am. Chem. Soc. 2000, 122, 6610.
Degl’Innocenti, A., Mordini, A., Pecchi, S., Pinzani, D., Reginato, G., and Ricci, A. Synlett 1992, 803.
Mordini, A., Pecchi, S., Capozzi, G., Capperucci, A., Degl’Innocenti, A., Reginato, G., and Ricci, A. J. Org. Chem. 1994, 59, 4784.
Mordini, A., Valacchi, M., Pecchi, S., Degl’Innocenti, A., and Reginato, G. Tetrahedron Lett. 1996, 37, 5209.
Gao, Y., Hanson, R. M., Klunder, J. M., Ko, S. Y., Masamune, H., and Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
Katsuki, T. and Martin, V. S. In Organic Reactions. Wiley, New York, 1996, Vol. 48, p. 3.
Rossiter, B. E. In Asymmetric Synthesis – Chiral Catalysis, Morrison, J. D. (ed.), Academic Press, New York, 1985, Vol. 5.
Mordini, A., Sbaragli, L., Valacchi, M., Russo, F., and Reginato, G. Chem. Commun. 2002, 778–779.
Mordini, A., Comes Franchini, M., and Bracchi, P. (unpublished results).
Hodgson, D. M., Miles, T. J., and Witherington, J. Synlett 2002, 310.
Hodgson, D. M., Miles, T. J., Witherington, J. J. Org. Chem. 2006, 71, 8510.
Mordini, A., Bindi, S., Pecchi, S., Degl’Innocenti, A., Reginato, G., and Serci, A. J. Org. Chem. 1996, 61, 4374.
Bird, C. W., and Hormozi, N. Tetrahedron Lett. 1990, 31, 3501.
Ichikawa, Y., Niitsuma, S., Kuniki, K., and Takita, T. J. Chem. Soc., Chem. Commun. 1988, 625.
Mordini, A., Bindi, S., Capperucci, A., Nistri, D., Reginato, G., and Valacchi, M. J. Org. Chem. 2001, 66, 3201.
Fleming, F. F. and Shook, B. C. Tetrahedron 2002, 58, 1–23.
Lambs, L., Singh, N. P., and Biellmann, J.-F. J. Org. Chem 1992, 57, 6301–6304.
Langer, P. and Freifeld, I. Org. Lett. 2001, 3, 3903–3905.
Babler, J. H.; Tortorello, A. J. J. Org. Chem 1976, 41, 885–887.
Le Corre, M., Hercouet, A., and Bessieres, B. Tetrahedron: Asymmetry 1995, 6, 683–684.
Majewski, J. and Snieckus, V. J. Org. Chem 1984, 49, 2682–2687.
Crotti, P., Di Bussolo, V., Favero, L., Macchia, F., Pineschi, M., and Napolitano, E. Tetrahedron 1999, 55, 5853–5866.
Benedetti, F., Berti, F., Fabrissin, S., Gianferrara, T., and Risaliti, A. J. Org. Chem 1991, 56, 3530–3537.
Corbel, B., and Durst, T. J. Org. Chem 1976, 41, 3648–3650.
Gaoni, Y. J. Org. Chem 1982, 47, 2564–2571.
Narjes, F., Bolte, O., Icheln, D., Konig, A., and Schaumann, E. J. Org. Chem 1993, 58, 626–632.
Apparu, M. and Barrelle, M. Tetrahedron Lett. 1976, 33, 2837–2840.
Apparu, M. and Barrelle, M. Tetrahedron 1978, 34, 1691–1697.
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Mordini, A., Peruzzi, D., Russo, F., Reginato, G. (2008). Highly Selective Metalation Reactions. In: Mordini, A., Faigl, F. (eds) New Methodologies and Techniques for a Sustainable Organic Chemistry. NATO Science Series II: Mathematics, Physics and Chemistry, vol 246. Springer, Dordrecht. https://doi.org/10.1007/978-1-4020-6793-8_15
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