Synthesis and activity of a new generation of ruthenium-based olefin metathesis catalysts coordinated with 1,3-dimesityl-4,5-dihydroimidazol-2-ylidene ligands

Organic Letters

Volumn 1, Issue 6, 1999, Pages 953-956

  Scholl, Matthias ^a   Ding, Sheng ^a   Lee, Choon Woo ^a   Grubbs, Robert H ^a  

^a California Institute of Technology ^*  (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; IMIDAZOLE DERIVATIVE; LIGAND; RUTHENIUM;

ARTICLE; CATALYSIS; CHEMISTRY;

ALKENES; CATALYSIS; IMIDAZOLES; LIGANDS; RUTHENIUM;

EID: 0033598258     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990909q     Document Type: Article

References (38)

1. For recent reviews on olefin metathesis, see: (a) Ivin, K. J. J. Mol. Catal. A-Chem. 1998, 133, 1-16.
2. (b) Grubbs, R. H.; Chang, S. Tetrahedron 1998, 54, 4413-4450.
3. (c) Randall, M. L.; Snapper, M. L. J. Mol. Catal. A-Chem. 1998, 133, 29-40.
4. (a) Schrock, R. R.; Murdzek, J. S.; Bazan, G. C.; Robbins, J.; Dimare, M.; O'Regan, M. J. Am. Chem. Soc. 1990, 112, 3875-3886.
5. (b) Bazan, G. C.; Khosravi, E.; Schrock, R. R.; Feast, W. J.; Gibson, V. C.; O'Regan, M. B.; Thomas, J. K.; Davis, W. M. J. Am. Chem. Soc. 1990, 112, 8378-8387.
6. (c) Bazan, G. C.; Oskam, J. H.; Cho, H. N.; Park, L. Y.; Schrock, R. R. J. Am. Chem. Soc. 1991, 113, 6899-6907.
7. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
8. (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
9. Kirkland, T. A.; Grubbs, R. H. J. Org. Chem. 1997, 62, 7310-7318.
10. (a) Scholl, M.; Trnka, T. M.; Morgan, J. P.; Grubbs, R. H. Tetrahedron Lett. 1999, 40, 2247-2250.
11. (b) Concurrently another research group reported similar results: Huang, J. K.; Stevens, E. D.; Nolan, S. P.; Petersen, J. L. J. Am. Chem. Soc. 1999, 121, 2674-2678.
12. (c) For a follow-up study, see: Ackermann, L.; Furstner, A.; Weskamp, T.; Kohl, F. J.; Herrmann, W. A. Tetrahedron Lett. 1999, 40, 4787-4790.
13. For initial reports on the 1,3-diaryl-4,5-dihydroimidazol-2-ylidenes, see: (a) Wanzlick, H.-W.; Kleiner, H. J. Angew. Chem. 1961, 37, 493.
14. (b) Wanzlick, H. W. Angew. Chem., Int. Ed. Engl. 1962, 1, 75-80.
15. (c) Wanzlick, H.-W.; Schikora, E. Chem. Ber. 1961, 94, 2389-2393.
16. (d) Wanzlick, H.-W.; Esser, F.; Kleiner, H. J. Chem. Ber. 1963, 96, 1208-1212.
17. (e) Wanzlick, H.-W.; Lachmann, B.; Schikora, E. Chem. Ber. 1965, 98, 3170-3177.
18. (f) Lachmann, B.; Wanzlick, H.-W. Justus Liebigs Ann. Chem. 1969, 729, 27.
19. (g) Lemal, D. M.; Kawano, K. I. J. Am. Chem. Soc. 1962, 84, 1761-1762.
20. (h) Lemal, D. M.; Lovald, R. A.; Kawano, K. I. J. Am. Chem. Soc. 1964, 86, 2518-2519.
21. For the first report of isolation of 1,3-dimesityl-4,5-dihydroimidazol-2-ylidenes, see: Arduengo, A. J.; Goerlich, J. R.; Marshall, W. J. J. Am. Chem. Soc. 1995, 117, 11027-11028.
22. For other examples of saturated carbene ligands, see: (a) Alder, R. W.; Allen, P. R.; Murray, M.; Orpen, A. G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1121-1123.
23. (b) Alder, R. W.; Blake, M. E.; Bortolotti, C.; Bufali, S.; Butts, C. P.; Linehan, E.; Oliva, J. M.; Orpen, A. G.; Quayle, M. A. Chem. Commun. 1999, 241-242.
24. Ding, S.; Feldmann, M. T.; Grubbs, R. H.; Goddard, W. A. J. Am. Chem. Soc. 1999, submitted.
25. Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887-3897.
26. For examples, see: (a) Hutchins, R. O.; Su, W.-Y.; Sivakumar, R.; Cistone, F.; Stercho, Y. P. J. Org. Chem. 1983, 48, 3412-3422.
27. (b) Dieck, H. t.; Verfürth, U.; Diblitz, K.; Ehlers, J.; Fendesak, G. Chem. Ber. 1989, 122, 129-131.
28. For example, see: Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215-7216. For a recent review of palladium-catalyzed amination of aryl halides, see: Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146.
29. For example, see: Wolfe, J. P.; Wagaw, S.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 7215-7216. For a recent review of palladium-catalyzed amination of aryl halides, see: Yang, B. H.; Buchwald, S. L. J. Organomet. Chem. 1999, 576, 125-146.
30. Saba, S.; Brescia, A.-M.; Kaloustain, M. K. Tetrahedron Lett. 1991, 32, 5031-5034.
31. Herrmann, W. A.; Köcher, C.; Goossen, L. J.; Artus, G. R. J. Chem. Eur. J. 1996, 2, 1627-1636.
32. (a) Trnka, T. M.; Grubbs, R. H. Manuscript in preparation.
33. For reports of preparation and isolation of triazol-5-ylidenes starting from the 5-methoxytriazoles, see: (b) Enders, D.; Breuer, K.; Raabe, G.; Runsink, J.; Teles, J. H.; Melder, J. P.; Ebel, K.; Brode, S. Angew. Chem., Int. Ed. Engl. 1995, 34, 1021-1023.
34. (c) Teles, J. H.; Melder, J. P.; Ebel, K.; Schneider, R.; Gehrer, E.; Harder, W.; Brode, S.; Enders, D.; Breuer, K.; Raabe, G. Helv. Chim. Acta 1996, 79, 61-83.
35. +] 848.3306, found 848.3286.
36. For a study of the effects of olefin substitution on the ring-closing metathesis of dienes with complexes 1 and 2, see ref 4.
37. The decomposition half-life at 55°C in benzene of the (tricyclohexylphosphine)(1,3-dimesityl-4,5-dihydoimidazol-2-ylidene)methylidene ruthenium dichloride is approximately 6 h: Ulman, M. 1999, unpublished results. This is significantly longer than the corresponding half-life for the decomposition of bis(tricyclohexylphosphine)methylideneruthenium dichloride, which is only approximately 40 min: Ulman, M.; Grubbs, R. H. J. Org. Chem. 1999, accepted.
38. Léonard, A. Ruthenium. In Handbook on Toxicity of Inorganic Compounds; Seiler, H. G., Sigel, H., Sigel, A., Eds.; Dekker: New York, 1988; pp 571-574.