Ruthenium olefin metathesis catalysts bearing an N-fluorophenyl-N-mesityl- substituted unsymmetrical N-heterocyclic carbene

Organometallics

Volumn 26, Issue 9, 2007, Pages 2469-2472

  Vougioukalakis, Georgios C ^a   Grubbs, Robert H ^a  

^a California Institute of Technology   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CROSS METATHESIS; HETEROCYCLIC CARBENES; METATHESIS;

LIGANDS; OLEFINS; POLYMERIZATION; RUTHENIUM; SYNTHESIS (CHEMICAL);

CATALYSTS;

EID: 34248348750     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om0610593     Document Type: Article

References (33)

1. Grubbs, R. H. Handbook of Metathesis; Wiley-VCH: Weinheim, Germany, 2003.
2. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
3. (b) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
4. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett. 1999, 1, 953-956.
5. (a) Kingsbury, J. S.; Harrity, J. P. A.; Bonitatebus, P. J., Jr.; Hoveyda, A. H. J. Am. Chem. Soc. 1999, 121, 791-799.
6. (b) Garber, S. B.; Kingsbury, J. S.; Gray, B. L.; Hoveyda. A. H. J. Am. Chem. Soc. 2000, 122, 8168-8179.
7. Fürstner, A.; Ackermann, L.; Gabor, B.; Goddard, R.; Lehmann, C. W.; Mynott, R.; Stelzer, F.; Thiel, O. R. Chem.-Eur. J. 2001, 7, 3236-3253.
8. Dinger, M. B.; Nieczypor, P.; Mol, J. C. Organometallics 2003, 22, 5291-5296.
9. Vehlow, K.; Maechling, S.; Blechen, S. Organometallics 2006, 25, 25-28.
10. Ledoux, N.; Allaert, B.; Pattyn, S.; Mierde, H. V.; Vercaemst, C.; Verpoort, F. Chem.-Eur. J. 2006, 12, 4654-4661.
11. 3(NHC) complexes, alkyl-substituted NHCs are only slightly more electron donating than aryl-substituted ones and that saturated NHCs are somewhat less electron donating than their unsaturated analogues:
12. (b) Dorta, R.; Stevens, E. D.; Scott, N. M.; Costabile, C.; Cavallo, L.; Hoff, C. D.; Nolan, S. P. J. Am. Chem. Soc. 2005, 127, 2485-2495. For another classification of the relative σ-donor/π- acceptor properties of a series of NHC ligands see:
13. (c) Herrmann, W. A.; Schütz, J.; Frey, G. D.; Herdtweck, E. Organometallics 2006, 25, 2437-2448.
14. (a) Van Veldhuizen, J. J.; Garber, S. B.; Kingsbury, J. S.; Hoveyda, A. H. J. Am. Chem. Soc. 2002, 124, 4954-4955.
15. (b) Van Veldhuizen, J. J.; Gillingham, D. G.; Garber, S. B.; Kataoka, O.; Hoveyda, A. H. J. Am. Chem. Soc. 2003, 125, 12502-12508.
16. (c) Gillingham, D. G.; Kataoka, O.; Garber, S. B.; Hoveyda, A. H. J. Am. Chem. Soc. 2004, 126, 12288-12290.
17. (d) Van Veldhuizen, J. J.; Campbell, J. E.; Giudici, R. E.; Hoveyda, A. H. J. Am. Chem. Soc. 2005, 127, 6877-6882.
18. Ritter, T.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2006, 128, 11768-11769.
19. 2IMes parent complex 2. For a recent decomposition study in ruthenium-catalyzed olefin metathesis reactions see: Hong, S. H.; Day, M. W.; Grubbs, R. H. J. Am. Chem. Soc. 2004, 126, 7414-7415.
20. (a) Perera, S. D.; Shaw, B. L. Inorg. Chim. Acta 1995, 228, 127-131. For related review articles see:
21. (b) Kiplinger, J. L.; Richmond, T. G.; Osterberg, C. E. Chem. Rev. 1994, 94, 373-431.
22. (c) Kulawiec, R. J.; Crabtree, R. H. Coord. Chem. Rev. 1990, 99, 89-115.
23. Waltman, A. W.; Grubbs, R. H. Organometallics 2004, 23, 3105-3107.
24. Dwyer, C. L.; Kirk, M. M.; Meyer, W. H.; van Rensburg, W. J.; Forman, G. S. Organometallics 2006, 25, 3806-3812.
25. Sanford, M. S. Ph.D. Thesis, California Institute of Technology, Pasadena, 2001.
26. Review articles on π-π stacking interactions: (a) Williams, J. H. Acc. Chem. Res. 1993, 26, 593-598.
27. (b) Janiak, C. J. Chem. Soc., Dalton Trans. 2000, 3885-3896. For a more recent example of intramolecular π-π stacking interactions see:
28. (c) Mandal, D.; Gupta, B. D. Organometallics 2006, 25, 3305-3307.
29. (d) Mandai, D.; Gupta, B. D. Organometallics 2007, 26, 658-670.
30. All reactions were performed at least in duplicate to confirm reproducibility. For experimental procedures see: Ritter, T.; Hejl, A.; Wenzel, A. G.; Funk, T. W.; Grubbs, R. H. Organometallics 2006, 25, 5740-5745.
31. (a) Sanford, M. S.; Ulman, M.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 749-750.
32. (b) Sanford, M. S.; Love, J. A.; Grubbs, R. H. J. Am. Chem. Soc. 2001, 123, 6543-6554.
33. Chatterjee, A. K.; Choi, T. L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360-11370.