Abstract
Ruthenium- and rhodium-based catalysts can be designed and finely tuned to some extent so as to mediate either carbene transfer to olefins (e.g., olefin cyclopropanation) or olefin metathesis. The different outcome of the reactions can be quite simply predicted based on either the ability or the absence of ability of the metal center to coordinate both the carbene and the olefin. Several available coordination sites at the metal center are favorable for metathesis to the prejudice of olefin cyclopropanation.
This is a preview of subscription content, log in via an institution to check access.
Similar content being viewed by others
References
T. Ye and M. A. McKervey,Chem. Rev., 1994,94, 1091.
G. Maas,Top. Curr. Chem., 1987,137, 75.
A. F. Noels and A. Demonceau,Applied Homogeneous Catalysis with Organometallic Compounds, VCH, Weinheim, 1996, 733.
Yu. V. Tomilov, V. A. Dokichev, U. M. Dzhemilev, and O. M. Nefedov,Uspekhi khimii, 1993, 847 [Russ. Chem. Rev., 1993,62, 799 (Engl. Transl.)].
M. Putala and D. A. Lemenovskii,Uspekhi khimii, 1994. 207 [Russ. Chem. Rev., 1994,63, 197 (Engl. Transl.)].
M. P. Doyle,Acc. Chem. Rev., 1986,86, 919.
A. Padwa and D. J. Austin,Angew. Chem. Int. Ed. (Engl.), 1994,33, 1797.
A. J. Anciaux, A. J. Hubert, A. F. Noels, N. Petiniot, and P. Teyssé,J. Org. Chem., 1980,45, 695.
A. Demonceau, A. F. Noels, E. Saive, and A. J. Hubert,J. Mol. Catal. A, 1992,76, 123.
A. W. Stumpf, E. Saive, A. Demonceau, and A. F. Noels,J. Chem. Soc., Chem. Commun., 1995, 1127.
P. Schwab, M. B. France, J. W. Ziller, and R. H. Grubbs,Angew. Chem. Int. Ed. (Engl.), 1995,34, 2039.
M. B. France, J. Feldman, and R. H. Grubbs,J. Chem. Soc., Chem. Commun., 1994, 1307.
P. Schwab, R. H. Grubbs, and J. W. Ziller,J. Am. Chem. Soc., 1996,118, 100.
M. A. Hillmeyer, A. D. Benedicto, S. T. Nguyen, Z. Wu, and R. H. Grubbs,Macromol. Symp., 1995,89, 411.
S. T. Nguyen, R. H. Grubbs, and J. W. Ziller,J. Am. Chem. Soc., 1993,115, 9856.
T. R. Cundari and M. S. Gordon,J. Am. Chem. Soc., 1991,113, 5231.
T. R. Cundari and M. S. Gordon,Organometallics, 1992,114, 539.
P. J. Brothers and W. R. Roper,Chem. Rev., 1988,88, 1293.
A. F. Noels, A. Demonceau, and E. Saive,Advances in Catalyst Design, Ed. 2, Vol. 2, World Scientific, Singapore, 1993, 73.
K. J. Ivin and J. C. Mol,Olefin Metathesis and Metathesis Polymerization, Academic Press Ltd, London, 1997.
R. Noyori,Asymmetric Catalysis in Organic Synthesis, Wiley and Sons, New York, 1994, 203.
P. W. Jennings and L. L. Johnson,Chem. Rev., 1994,94, 2241.
A. Demonceau, A. F. Noels, J. L. Costa, and A. J. Hubert,J. Mol. Catal., 1990,58, 21.
M. C. Pirrung and A. T. Morehead, Jr.,J. Am. Chem. Soc., 1994,116, 8991.
M. Brookhart and W. B. Studabaker,Chem. Rev., 1987,97, 411.
M. P. Doyle and M. A. McKervey,J. Chem. Soc., Chem. Commun., 1997, 983.
K. C. Brown and T. Kodadek,J. Am. Chem. Soc., 1992,114, 8336.
F. A. Cotton, K. R. Dunbar, and M. G. Verbruggen,J. Am. Chem. Soc., 1987.109, 5498.
F. A. Cotton, V. M. Miskowski, and B. Zhong,J. Am. Chem. Soc., 1989,111, 6177.
A. F. Noels, A. Demonceau, E. Carlier, A. J. Hubert, R. L. Marquez-Silva, and R. A. Sanchez-Delgado,J. Chem. Soc., Chem. Commun., 1988, 783.
A. Demonceau, A. W. Stumpf, E. Saive, and A. F. Noels,Macromolecules, 1997,30, 3127.
H. Nishiyama, Y. Itoh, H. Matsumoto, S.-B. Park, and K. Itoh,J. Am. Chem. Soc., 1994,116, 2223.
H. Nishiyama, K. Aoki, H. Itoh, T. Iwamura, N. Sakata, O. Kurihara, and Y. Motoyama,Chem. Lett., 1996, 1071.
M. P. Doyle, C. S. Peterson, Q. L. Zhou, and H. Nishiyama,J. Chem. Soc., Chem. Commun., 1997, 211.
F. Simal, A. Demonceau, A. F. Noels, D. R. T. Knowles, S. O'Leary, P. M. Maitlis, and O. Gusev,J. Organomet. Chem., 1998,558, 163.
M. T. Youinou, J. Kress, J. Fisher, A. Aguero, and J. A. Osborn,J. Am. Chem. Soc., 1988,110, 1488.
J. Kress and J. A. Osborn,Angew. Chem. Int. Ed. (Engl.), 1992,31, 1585.
R. H. Grubbs, S. J. Mitter, and G. C. Fu,Acc. Chem. Res., 1995,28, 446.
E. L. Dias and R. H. Grubbs,Organometallics, 1998,17, 2758.
Author information
Authors and Affiliations
Additional information
Translated fromIzvestiya Akademii Nauk, Seriya Khimicheskaya, No. 7, pp. 1219–1224, July, 1999.
Rights and permissions
About this article
Cite this article
Noels, A.F., Demonceau, A. & Jan, D. Late transition metal-based catalysts for olefin cyclopropanation or olefin metathesis. Importance of catalyst unsaturation. Russ Chem Bull 48, 1206–1211 (1999). https://doi.org/10.1007/BF02495278
Received:
Issue Date:
DOI: https://doi.org/10.1007/BF02495278