Abstract
The catalytic carbonylation reactions of α-haloketones in the presence of palladium compounds were studied. Chloroketones were selectively converted into β-ketoesters, whereas bromoacetophenone was partially reduced to acetophenone. The reaction rate at atmospheric pressure was much lower than that at an elevated pressure. A reaction mechanism was proposed.
Similar content being viewed by others
REFERENCES
Kenner, G.W. and Todd, A., Heterocyclic Compounds, Weissberger, A., Ed., New York: Wiley, 1957, vol. 6.
Brown, D.J., The Chemistry of Heterocyclic Compounds, Weissberger, A., Ed., New York: Wiley, 1962, vol. 16, 22.
Benningshof, J.C.J., Blaauw, R.H., Van Ginkel, A.E., Rutjes, F.P.J.T., Fraanje, J., Goubitz, K., Schenk, H., and Hiemstra, H., Chem. Commun., 2000, no. 16, p. 1465.
Compernolle, F., Baens, N., and Hoornaert, G.J., Bull. Soc. Chim. Belg., 1997, vol. 106, p. 433.
Coffey, D.S., Overman, L.E., and Stappenbeck, F., J. Am. Chem. Soc., 2000, vol. 122, p. 4904.
Haudrechy, A., Chassaing, C., Riche, C., and Langlois, Y., Tetrahedron, 2000, vol. 56, p. 3181.
Backhaus, D., Tetrahedron Lett., 2000, vol. 41, p. 2087.
Raboin, J.-C., Beley, M., and Kirsch, G., Tetrahedron Lett., 2000, vol. 41, p. 1175.
Jpn. Patent 08302286, 1996.
EEC Patent 950727, 1999.
Toth, E., Van Uffelen, I., Helm, L., Morbach, A.E., Ladd, D., Briley-Sabø K., and Kellar K.E., Magn. Res. Chem., 1998, vol. 36, p. 125.
Jpn. Patent 09318814, 1997.
EEC Patent 881253, 1998.
Jpn. Patent 1060275, 1998.
Hoeblel, D., Reinerf, T., and Schmidt, A., J. Sol-Gel Technol., 1997, vol. 10, p. 115.
Colguhoun, H.M., Thompson, D.J., and Twigg, M.V., Carbonylation: Direct Synthesis of Carbonyl Compounds, New York: Plenum, 1991.
Parshall, G.W. and Itell, S.D., Homogeneous Catalysis: The Applications and Chemistry of Catalysis by Soluble Transition Metal Complexes, New York: Wiley, 1992.
Gulevich, Yu.V., Bumagin, N.A., and Beletskaya, I.P., Usp. Khim., 1988, vol. 57, p. 529.
Lapidus, A.L. and Pirozhkov, S.D., Usp. Khim., 1989, vol. 58, p. 197.
Stille, J.K. and Wong, P.K., J. Org. Chem., 1975, vol. 40, p. 532.
Choudary, B.M., Reddy, N.P., and Jamil, M.Z., Polyhedron, 1986, vol. 5, p. 911.
Adapa, S.R. and Pasad, C.S.N., J. Chem. Soc., Perkin Trans., 1989, no. 9, p. 1706.
Cavinato, G. and Toniolo, L., J. Mol. Catal., A: Chem., 1999, vol. 143, p. 325.
Gore, P.H., Chem. Rev., 1955, vol. 55, p. 229.
Moser, R.W., Wong, A.W., and Kildahl, N.K., J. Am. Chem. Soc., 1988, vol. 110, p. 2816.
Hidai, M., Kokura, M., and Uchida, Y., J. Organomet. Chem., 1973, vol. 52, p. 43.
Cassar, L., Foa, M., and Gardano, A., J. Organomet. Chem., 1976, vol. 121, p. 55.
Alper, H., Hashem, K., and Heveling, J., Organometallics, 1982, vol. 1, p. 775.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Lapidus, A.L., Eliseev, O.L., Bondarenko, T.N. et al. Carbonylation of α-Haloketones. Kinetics and Catalysis 45, 234–238 (2004). https://doi.org/10.1023/B:KICA.0000023797.89865.e5
Issue Date:
DOI: https://doi.org/10.1023/B:KICA.0000023797.89865.e5