Latent ruthenium olefin metathesis catalysts that contain an N-heterocyclic carbene ligand

Organometallics

Volumn 23, Issue 23, 2004, Pages 5399-5401

  Ung, Thay ^a   Hejl, Andrew ^b   Grubbs, Robert H ^b   Schrodi, Yann ^a  

^a Materia Inc   (United States)

^b CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

LIGANDS; RING-CLOSING METATHESIS (RCM); RING-OPENING METATHESIS POLYMERIZATION (ROMP); X-RAY STRUCTURES;

CATALYSTS; CHEMICAL BONDS; COMPLEXATION; RING OPENING POLYMERIZATION; RUTHENIUM; SYNTHESIS (CHEMICAL);

OLEFINS;

EID: 9144245653     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0493210     Document Type: Article

References (27)

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3. (c) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003; Vols. 2 and 3.
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7. (d) Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18-29.
8. (e) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, Germany, 2003; Vol. 1.
9. (a) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1992, 114, 3974-3975.
10. (b) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
11. (c) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1986, 118, 100-110.
12. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
13. Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda, A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179.
14. (a) Sanford, M. S.; Love, J. A.; Grubbs, R. H. Organometallics 2001, 20, 5314-5318.
15. (b) Love, J. A.; Morgan, J. P.; Trnka, T. M.; Grubbs, R. H. Angew. Chem., Int. Ed. 2002, 41, 4035-4037.
16. van der Schaaf, P. A.; Kolly, R.; Kirner, H.-J.; Rime, P.; Mühlebach, A.; Hafner, A. J. Organomet? Chem. 2000, 606, 65-74.
17. 1H NMR singlets described are consistent with a C symmetry and free rotation of the sIMes ligand around the Ru-C bond (on the NMR time scale).
18. Attempts to measure the kinetics of the approach to equilibrium were hampered by a decomposition process concurrent with the 4a ↔4b isomerization process.
19. Ruthenium complexes containing chelating bis-phosphine Uganda and cis chlorides have been described: (a) Hansen, S. M.; Volland, M. A. O.; Rominger, F.; Eisenträger, F.; Hofman, P. Angew. Chem., Int. Ed. 1999, 35, 1273-1276. (b) Hansen, S. M.; Rominger, F.; Metz, M.; Hofman, P. Chem. Eur. J. 1999, 5, 557-566. (c) Volland, M. A. O.; Straub, B. F.; Gruber, I.; Rominger, F.; Hofman, P. J. Organomet. Chem. 2001, 617, 288-291. (d) Nieczypor, P.; van Leeuwen, P. W. N. M.; Mol, J. C.; Lutz, M.; Spek, A. L. J. Organomet. Chem. 2001, 625, 58-66.
20. Ruthenium complexes containing chelating bis-phosphine Uganda and cis chlorides have been described: (a) Hansen, S. M.; Volland, M. A. O.; Rominger, F.; Eisenträger, F.; Hofman, P. Angew. Chem., Int. Ed. 1999, 35, 1273-1276. (b) Hansen, S. M.; Rominger, F.; Metz, M.; Hofman, P. Chem. Eur. J. 1999, 5, 557-566. (c) Volland, M. A. O.; Straub, B. F.; Gruber, I.; Rominger, F.; Hofman, P. J. Organomet. Chem. 2001, 617, 288-291. (d) Nieczypor, P.; van Leeuwen, P. W. N. M.; Mol, J. C.; Lutz, M.; Spek, A. L. J. Organomet. Chem. 2001, 625, 58-66.
21. Ruthenium complexes containing chelating bis-phosphine Uganda and cis chlorides have been described: (a) Hansen, S. M.; Volland, M. A. O.; Rominger, F.; Eisenträger, F.; Hofman, P. Angew. Chem., Int. Ed. 1999, 35, 1273-1276. (b) Hansen, S. M.; Rominger, F.; Metz, M.; Hofman, P. Chem. Eur. J. 1999, 5, 557-566. (c) Volland, M. A. O.; Straub, B. F.; Gruber, I.; Rominger, F.; Hofman, P. J. Organomet. Chem. 2001, 617, 288-291. (d) Nieczypor, P.; van Leeuwen, P. W. N. M.; Mol, J. C.; Lutz, M.; Spek, A. L. J. Organomet. Chem. 2001, 625, 58-66.
22. Ruthenium complexes containing chelating bis-phosphine Uganda and cis chlorides have been described: (a) Hansen, S. M.; Volland, M. A. O.; Rominger, F.; Eisenträger, F.; Hofman, P. Angew. Chem., Int. Ed. 1999, 35, 1273-1276. (b) Hansen, S. M.; Rominger, F.; Metz, M.; Hofman, P. Chem. Eur. J. 1999, 5, 557-566. (c) Volland, M. A. O.; Straub, B. F.; Gruber, I.; Rominger, F.; Hofman, P. J. Organomet. Chem. 2001, 617, 288-291. (d) Nieczypor, P.; van Leeuwen, P. W. N. M.; Mol, J. C.; Lutz, M.; Spek, A. L. J. Organomet. Chem. 2001, 625, 58-66.
23. (a) Prühs, S.; Lehman, C. W.; Fürstner, A. Organometallics 2004, 23, 280-287.
24. (b) Slugovc, C.; Perner, B.; Selzer, F.; Mereiter, K. Organometallics 2004, 23, 3622-3626.
25. A related complex with cis neutral liganda and cis anionic pentafluorophenoxide ligands has been reported: Conrad, J. C.; Amoroso, D.; Czechura, P.; Yap, G. P. A.; Fogg, D. E. Organometallics 2003, 22, 3634-3636.
26. A related vinylcarbene ruthenium complex containing cis chlorides has also been reported: Trnka, T. M.; Day, M. W.; Grubbs, R. H. Organometallics 2001, 20, 3845-3847.
27. See ref 13 for a discussion on the conformation of olefin metathesis intermediates.