Olefin metathesis-active ruthenium complexes bearing a nucleophilic carbene ligand

Journal of the American Chemical Society

Volumn 121, Issue 12, 1999, Pages 2674-2678

  Huang, Jinkun ^a   Stevens, Edwin D ^a   Nolan, Steven P ^a   Petersen, Jeffrey L ^b  

^a UNIVERSITY OF NEW ORLEANS   (United States)

^b WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BIS(2,4,6 TRIMETHYLPHENYL)IMIDAZOL 2 YLIDENE; ALKENE; IMIDAZOLE DERIVATIVE; RUTHENIUM; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL REACTION; COMPLEX FORMATION; CRYSTAL STRUCTURE; ENTHALPY; MOLECULAR STABILITY; STRUCTURE ANALYSIS; THERMODYNAMICS; THERMOSTABILITY; X RAY CRYSTALLOGRAPHY; X RAY DIFFRACTION;

EID: 0033620417     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja9831352     Document Type: Article

References (46)

1. (a) Pignolet, L. H., Ed. Homogeneous Catalysis with Metal Phosphine Complexes; Plenum: New York, 1983.
2. (b) Parshall, G. W.; Ittel, S. D. Homogeneous Catalysis; Wiley-Interscience: New York, 1992.
3. Collman, J. P.; Hegedus, L. S.; Norton, J. R.; Finke, R. G. Principles and Applications of Organotransition Metal Chemistry, 2nd ed.; University Science: Mill Valley, CA, 1987.
4. (a) Kubas, G. J. Acc. Chem. Res. 1988, 21, 120-128 and references therein.
5. (b) Gonzalez, A. A.; Mukerjee, S. L.; Chou, S.-J.; Zhang, K.; Hoff, C. D. J. Am. Chem. Soc. 1988, 110, 4419-4421.
6. (c) Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9858-9859.
7. (d) Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856-9857.
8. (a) For a brief review of the first carbene of this type, see: Wanzlick, H.-W. Angew. Chem., Int. Ed. Engl. 1962, 1, 75-80. (b) For a review of these ligands as phosphine mimics, see: Lappert, M. F. J. Organomet. Chem. 1988, 358, 185-213. (c) For a review dealing with carbene steric factors and stability, see: Arduengo, A. J., III; Krafczyk, R. Chem. Z. 1998, 32, 6-14.
9. (a) For a brief review of the first carbene of this type, see: Wanzlick, H.-W. Angew. Chem., Int. Ed. Engl. 1962, 1, 75-80. (b) For a review of these ligands as phosphine mimics, see: Lappert, M. F. J. Organomet. Chem. 1988, 358, 185-213. (c) For a review dealing with carbene steric factors and stability, see: Arduengo, A. J., III; Krafczyk, R. Chem. Z. 1998, 32, 6-14.
10. (a) For a brief review of the first carbene of this type, see: Wanzlick, H.-W. Angew. Chem., Int. Ed. Engl. 1962, 1, 75-80. (b) For a review of these ligands as phosphine mimics, see: Lappert, M. F. J. Organomet. Chem. 1988, 358, 185-213. (c) For a review dealing with carbene steric factors and stability, see: Arduengo, A. J., III; Krafczyk, R. Chem. Z. 1998, 32, 6-14.
11. Herrmann, W. A.; Goossen, L. J.; Spiegler, M. J. Organomet. Chem. 1997, 547, 357-366.
12. For a comprehensive review, see: Herrmann, W. A.; Köcher, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2163-2187.
13. Arduengo, A. J., III; Harlow, R. L.; Kline, M. J. J. Am. Chem. Soc. 1991, 113, 361-363.
14. Arduengo, A. J., III; Gamper, S. F.; Calabrese, J. C.; Davidson, F. J. Am. Chem. Soc. 1994, 116, 4391-4393.
15. Adducts of a related carbene ligand with Group II and XII metallocenes have been reported: Arduengo, A. J., III; Davidson, F.; Krafczyk, R.; Marshall, W. J., Tamm, M. Organometallics 1998, 17, 3375-3382.
16. (a) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H.; Ziller, J. W. J. Am Chem. Soc. 1992, 114, 3974-3975.
17. (b) Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858-9859.
18. (c) Schwab, P.; France, M. B.; Grubbs, R. H.; Ziller, J. W. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
19. (d) Belderrain, T. R.; Wilhelm, T. A.; Grubbs, R. H. Organometallics 1997, 16, 4001-4003.
20. (e) Wilhelm, T. E.; Belderrain, T. R.; Brown, S. N.; Grubbs, R. H. Organometallics 1997, 16, 3867-3869.
21. (f) Wolf, J.; Stüer, W.; Grünwald, C.; Werner, H.; Schwab, P.; Schulz, M. Angew. Chem., Int. Ed. 1998, 37, 1124-1126.
22. (g) Katayama, H.; Ozawa, F. Organometallics 1998, 17, 5190-5196.
23. (a) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-452.
24. (b) Kirkland, T. A.; Grubbs, R. H. J. Org. Chem. 1997, 62, 7310-7318 and references cited.
25. (c) Fürstner, A.; Picquet, M.: Bruneau, C.; Dixneuf, P. H. J. Chem. Soc., Chem. Commun. 1998, 1315-1316.
26. (d) Schuster, M.; Blechert, S. Angew. Chem., Int. Ed. Engl. 1997, 36, 2036-2056.
27. (e) Fürstner, A. Top. Catal. 1997, 4, 285-299.
28. (a) Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am Chem. Soc. 1997, 119, 3887-3897.
29. (b) Ulman, M.; Grubbs, R. H. Organometallics 1998, 17, 2484-2489.
30. Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
31. Fagan, P. J.; Ward, M. D.; Caspar, J. V.; Calabrese, J. C.; Krusic, P. J. J. Am. Chem. Soc. 1988, 110, 2981-2983.
32. Campion, B. K.; Heyn, R. H.; Tilley, T. D. J. Chem. Soc., Chem. Commun. 1988, 278-280. Metrical data for 5: Ru-P, 2.383(1) Å; Ru-Cl, 2.378(1) Å; Ru-Cp*(c), 1.771(1) Å; Cl-Ru-P, 91.2(1)°; Cl-Ru-Cp*(c), 129.9 (1)°;C(l)-Ru-Cp*(c), 138.9(1)°.
33. Arduengo, A. J., III; Dias, H. V. R.; Calabrese, J. C.; Davidson, F. J. Am. Chem. Soc. 1992, 114, 9724-9725.
34. Solution calorimetric protocol is similar to that previously reported: Serron, S. A.; Huang, J.; Nolan, S. P. Organometallics 1998, 17, 534-539.
35. Luo, L.; Nolan S. P. Organometallics 1994, 13, 4781-4786.
36. 3)Cl: 40.4 ppm (see ref 15).
37. Shannon, R. D. Acta Crystallogr. 1976, A32, 751-767.
38. Tolman, C. A. Chem. Rev. 1977, 77, 313-348.
39. In the course of the redaction of this manuscript, a communication of a bis(carbene)ruthenium analogue to Grubbs's catalyst appeared: Weskamp, T.; Schattenmann, W. C.; Spiegler, M.; Herrmann, W. A. Angew. Chem., Int. Ed. 1998, 37, 2490-2493.
40. Cucullu, M. E.; Li, C.; Nolan, S. P.; Nguyen, S. T.; Grubbs, R. H. Organometallics 1998, 17, 5565-5568.
41. 3, not IMes, according to the thermochemical study.
42. Perrin, D. D.; Armarego, W. L. F. Purification of Laboratory Chemicals, 3rd ed.; Pergamon Press: New York, 1988.
43. Ojelund, G.; Wadsö, I. Acta Chem. Scand. 1968, 22, 1691-1699.
44. Kilday, M. V. J. Res. Natl. Bur. Stand. (U. S.) 1980, 85, 467-481.
45. (a) Nolan, S. P.; Hoff, C. D.; Landrum, J. T. J. Organomet. Chem. 1985, 282, 357-362.
46. (b) Nolan, S. P.; Lopez de la Vega, R.; Hoff, C. D. Inorg. Chem. 1986, 25, 4446-4448.