Abstract
A convenient synthetic approach to the adducts (C n F2n+1)3BNHR2 (n = 2–4, 6; R = Me, Et) was developed, based on the reaction of lithium perfluoroalkyls with dichloro(dialkylamino)boranes at temperatures below −90°C. The target products can be synthesized with preparative yields of 50–90%.
Similar content being viewed by others
References
Piers, W.E., Advances in Organometallic Chemistry, San Diego: Elsevier Academic Press, Inc., 2005, vol. 52, p. 1.
Bardin, V.V., Frohn, H.J., Main Group Met. Chem., 2002, vol. 25, no. 10, p. 589.
Chivers, T., J. Fluorine Chem., 2002, vol. 115, no. 1, p. 1.
Frohn, H.J. and Bardin, V.V., Organometallics, 2001, vol. 20, no. 23, p. 4750.
Piers, W.E. and Chivers, T., Chem. Soc. Rev., 1997, vol. 26, no. 5, p. 345.
Krossing, I. and Raabe, I., Angew. Chem., Int. Edit., 2004, vol. 43, no. 16, p. 2066.
Focante, F., Mercandelli, P., Sironi, A., and Resconi, L., Coord. Chem. Rev., 2006, vol. 250, nos. 1–2, p. 170.
Pawelke, G. and Burger, H., Coord. Chem. Rev., 2001, vol. 215, p. 243.
Brauer, D.J., Burger, H., Dorrenbach, F., Krumm, B., Pawelke, G., and Weuter, W., J. Organomet. Chem., 1990, vol. 385, no. 2, p. 161.
Ansorge, A., Brauer, D.J., Burger, H., Dorrenbach, F., Krumm, B., and Pawelke, G., J. Fluorine Chem., 1991, vol. 54, nos. 1–3, p. 181.
Pawelke, G. and Burger, H., Appl. Organomet. Chem., 1996, vol. 10, nos. 3–4, p. 147.
Brauer, D.J., Chebude, Y., and Pawelke, G., J. Fluorine Chem., 2001, vol. 112, no. 2, p. 265.
Pawelke, G. and Willner, H., Z. Anorg. Allg. Chem., 2005, vol. 631, no. 4, p. 759.
Volbach, W. and Ruppert, I., Tetrahedron Lett., 1983, vol. 24, no. 49, p. 5509.
Ruppert, I., J. Fluorine Chem., 1985, vol. 29, nos. 1–2, p. 98.
Pawelke, G., J. Fluorine Chem., 1989, vol. 42, no. 3, p. 429.
Frohn, H.J., Adonin, N.Y., and Bardin, V.V., Main Group Met. Chem., 2001, vol. 24, no. 12, p. 845.
Adonin, N.Y., Bardin, V.V., and Frohn, H.-J., Z. Anorg. Allg. Chem., 2007, vol. 633, no. 4, p. 647.
Abo-Amer, A., Adonin, N.Y., Bardin, V.V., Fritzen, P., Frohn, H.J., and Steinberg, C., J. Fluorine Chem., 2004, vol. 125, no. 11, p. 1771.
Adonin, N.Y., Frohn, H.-J., and Bardin, V.V., Organometallics, 2007, vol. 26, no. 9, p. 2420.
Mikhailov, B.M. and Bubnov, Yu.N., Bororganicheskie soedineniya v organicheskom sinteze (Organoboron Compounds in Organic Synthesis), Moscow: Nauka, 1977.
Kolomeitsev, A.A. Kadyrov, A.A., Szczepkowska-Sztolcman, J., Milewska, M., Koroniak, H., Bissky, G., Barten, J.A., and Röschenthaler, G.-V., Tetrahedron Lett., 2003, vol. 44, no. 45, p. 8273.
Uno, H. and Suzuki, H., Synlett., 1993, no. 2, p. 91.
Johncock, P., J. Organomet. Chem., 1969, vol. 19, no. 2, p. 257.
Frohn, H.-J., Adonin, N.Y., and Bardin, V.V., Main Group Met. Chem., 2001, vol. 24, no. 12, p. 845.
Abo-Amer, A., Adonin, N.Y., Bardin, V.V., Fritzen, P., Frohn, H.-J., and Steinberg, C., J. Fluorine Chem., 2004, vol. 125, no. 11, p. 1771.
Niedenzu, K. and Dawson, J.W., J. Am. Chem. Soc., 1959, vol. 81, no. 14, p. 3561.
Brauer, D.J., Bürger, H., Dorrenbach, F., Pawelke, G., and Weuter, W., J. Organomet. Chem., 1989, vol. 378, no. 2, p. 125.
Bürger, H., Grunwald, M., and Pawelke, G., J. Fluorine Chem., 1986, vol. 31, no. 1, p. 89.
Bernhardt, E., Brauer, D.J., Köckerling, M., and Pawelke, G., Z. Anorg. Allg. Chem., 2007, vol. 633, no. 7, p. 947.
Brauer, D.J., Brger, H., Dorrenbach, F., Krumm, B., Pawelke, G., and Weuter, W., J. Organomet. Chem., 1990, vol. 385, no. 2, p. 161.
Lazerte, J.D., Hals, L.J., Reid, T.S., and Smith, G.H., J. Am. Chem. Soc., 1953, vol. 75, no. 18, p. 4525.
Author information
Authors and Affiliations
Corresponding author
Additional information
Original Russian Text © N.Yu. Adonin, V.V. Bardin, U. Flörke, H.-J. Fron, 2011, published in Zhurnal Obshchei Khimii, 2011, Vol. 81, No. 3, pp. 413–420.
An erratum to this article can be found at http://dx.doi.org/10.1134/S1070363211050252
Rights and permissions
About this article
Cite this article
Adonin, N.Y., Bardin, V.V., Flörke, U. et al. New approach to the synthesis of tris(perfluoroalkyl)borane adducts with dialkylamines. Russ J Gen Chem 81, 509–516 (2011). https://doi.org/10.1134/S107036321103011X
Received:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S107036321103011X