Abstract
Different modifications of the Heck reaction involving the activation of carbon-halogen and carbon-oxygen bonds by palladium (styrene phenylation with iodobenzene or benzoic anhydride and iodobenzene carbonylation, reductive coupling, and reduction) are studied by in situ 31P NMR spectroscopy. The catalytic cycles of the reactions include oxidative addition to Pd(0) formed in situ. The product composition in this step depends strongly on the composition of the reaction mixture, which is related to PhX conversion in the main catalytic process and with the nature of the catalyst precursor. A new hypothesis as to the mechanism of the catalytic cycle in alkene arylation in the presence of phosphine ligands is suggested. This hypothesis is consistent with NMR monitoring data and with the value of the kinetic isotope effect.
Similar content being viewed by others
REFERENCES
Amatore, C., Carre, E., Jutand, A., M’Barki, M.A., and Meyer, G., Organometallics, 1995, vol. 14, no.12, p. 5605.
Amatore, C. and Jutand, A., Acc. Chem. Res., 2000, vol. 33, no.5, p. 314.
Amatore, C. and Jutand, A., J. Organomet. Chem., 1999, vol. 576, nos.1–2, p. 254.
Amatore, C., Carre, E., Jutand, A., and Medjour, Y., Organometallics, 2002, vol. 21, no.21, p. 4540.
Nagayama, K., Kawataka, F., Sakamota, M., Shimizu, I., and Yamamoto, A., Chem. Lett., 1995, no. 5, p. 367.
Garrou, P.E. and Heck, R.F., J. Am. Chem. Soc., 1976, vol. 98, no.14, p. 4115.
Amatore, C., Azzabi, M., and Jutand, A., J. Am. Chem. Soc., 1991, vol. 113, no.22, p. 8375.
Shmidt, A.F. and Khalaika, A., Kinet. Katal., 1998, vol. 39, no.6, p. 875.
Herrmann, W.A., Elison, M., Fischer, M., Kocher, C., and Artus, G.R.J., Angew. Chem., 1995, vol. 107, no.21, p. 2602.
Calo, V., Nacci, A., Lopez, L., and Mannarini, N., Tetrahedron Lett., 2000, vol. 41, no.46, p. 8973.
Shmidt, A.F., Smirnov, V.V., Starikova, O.V., and Elaev, A.V., Kinet. Katal., 2001, vol. 42, no.2, p. 223.
Casey, M., Lawless, J., and Shirran, C., Polyhedron, 2000, vol. 19, no.5, p. 517.
Buback, M., Perkovic, T., Redlich, S., and de Meijere, A., Eur. J. Org. Chem., 2003, no. 13, p. 2375.
Rosner, T., Bars, J., Pfaltz, A., and Blackmond, A., J. Am. Chem. Soc., 2001, vol. 123, no.9, p. 1848.
Shmidt, A.F. and Smirnov, V.V., Kinet. Katal., 2001, vol. 42, no.6, p. 800.
Fitton, P. and Rick B.B., J. Organomet. Chem., 1971, vol. 28, no.1, p. 287.
Stephan, M.S., Teunissen, A.J.J.M., Verzijl, G.K.M., and de Vries, J.G., Angew. Chem., 1998, vol. 37, no.5, p. 662.
Shmidt, A.F. and Smirnov, V.V., Kinet. Katal., 2000, vol. 41, no.6, p. 820.
Shmidt, A.F. and Smirnov, V.V., Kinet. Katal., 2002, vol. 43, no.2, p. 215.
Jutand, A., Negri, S., and de Vries, J.G., Eur. J. Inorg. Chem., 2002, no. 7, p. 1711.
Author information
Authors and Affiliations
Additional information
__________
Translated from Kinetika i Kataliz, Vol. 46, No. 4, 2005, pp. 529–535.
Original Russian Text Copyright © 2005 by Shmidt, Smirnov.
Rights and permissions
About this article
Cite this article
Shmidt, A.F., Smirnov, V.V. Oxidative Addition Step in Reactions Involving Palladium Activation of Carbon-Halogen and Carbon-Oxygen Bonds. Kinet Catal 46, 495–501 (2005). https://doi.org/10.1007/s10975-005-0101-0
Received:
Issue Date:
DOI: https://doi.org/10.1007/s10975-005-0101-0