Abstract
The main steps of the catalytic cycle of the alkene arylation reaction with the participation of anhydrides of aromatic acids as arylation agents were studied by 31P NMR spectroscopy. In contrast to the mechanism proposed earlier, palladium complexes containing benzoate anions as acidoligands were not found in the reaction mixture. It was found that the catalytic cycle of the reaction includes the steps of oxidative addition of Pd(0) formed in situ to the anhydride of acid, the substitution of acidoligand, and the elimination of the CO molecule. Further transformations probably take place according to the usual steps of the Heck reaction. It was shown that CO elimination is a limiting step.
Similar content being viewed by others
REFERENCES
Stephan, M.S., Teunissen, A.J., Verzijl, G.K.M., and De Vries, J.G., Angew. Chem., Int. Ed. Engl., 1998, vol. 37, no. 5, p. 662.
Beletskaya, I.P. and Cheprakov, A.V., Chem. Rev., 2000, vol. 100, no. 8, p. 3009.
Shmidt, A.F. and Smirnov, V.V., Kinet. Katal., 2000, vol. 41, no. 6, p. 820.
Nagayama, K., Kawataka, F., Sakamoto, M., Shimizu, I., and Yamamoto, A., Chem. Lett., 1995, no. 5, p. 367.
Garrou, P.E. and Heck, R., J. Am. Chem. Soc., 1976, vol. 98, no. 14, p. 4115.
Amatore, C. and Jutand, A., J. Organomet. Chem., 1999, vol. 576, nos. 1-2, p. 254.
Shmidt, A.F. and Khalaika, A., Kinet. Katal., 1998, vol. 39, no. 6, p. 875.
Author information
Authors and Affiliations
Rights and permissions
About this article
Cite this article
Shmidt, A.F., Smirnov, V.V. The NMR Study of the Mechanism of Alkene Arylation with Anhydrides of Aromatic Acids. Kinetics and Catalysis 43, 195–198 (2002). https://doi.org/10.1023/A:1015364310409
Issue Date:
DOI: https://doi.org/10.1023/A:1015364310409