Synthesis and characterization of new ruthenium-based olefin metathesis catalysts coordinated with bidentate Schiff-base ligands

Organometallics

Volumn 17, Issue 16, 1998, Pages 3460-3465

  Chang, Sukbok ^a   Jones II, LeRoy ^a   Wang, Chunming ^a   Henling, Lawrence M ^a   Grubbs, Robert H ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001645448     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om970910y     Document Type: Article

References (36)

1. For representative examples, see: (a) Grubbs, R. H.; Pine, S. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A. Eds.; Pergamon: New York, 1991; Vol. 5, Chapter 9.3. (b) Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic Press: San Diego, CA, 1997.
2. For representative examples, see: (a) Grubbs, R. H.; Pine, S. H. In Comprehensive Organic Synthesis; Trost, B. M., Fleming, I., Paquette, L. A. Eds.; Pergamon: New York, 1991; Vol. 5, Chapter 9.3. (b) Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic Press: San Diego, CA, 1997.
3. For representative examples, see: (a) Novak, B. M.; Risse, W.; Grubbs, R. H. Adv. Polymer. Sci. 1992, 102, 47. (b) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-552. (c) Hashimi, A. S. K. J. Prakt. Chem. 1997, 339, 195-199.
4. For representative examples, see: (a) Novak, B. M.; Risse, W.; Grubbs, R. H. Adv. Polymer. Sci. 1992, 102, 47. (b) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-552. (c) Hashimi, A. S. K. J. Prakt. Chem. 1997, 339, 195-199.
5. For representative examples, see: (a) Novak, B. M.; Risse, W.; Grubbs, R. H. Adv. Polymer. Sci. 1992, 102, 47. (b) Grubbs, R. H.; Miller, S. J.; Fu, G. C. Acc. Chem. Res. 1995, 28, 446-552. (c) Hashimi, A. S. K. J. Prakt. Chem. 1997, 339, 195-199.
6. (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.
7. (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.
8. (c) Bazan, G.G.; Oskam, J. H.; Cho, H.-N.; Park, L. Y.; Schrock, R. R. J. Am. Chem. Soc. 1991, 113, 6899-6907.
9. (a) Nguyen, S. T.; Johnson, L. K.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 3974-3975.
10. (b) Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1993, 115, 9858-9859.
11. (c) Wu, Z.; Nguyen, S. T.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1995, 117, 5503-5511.
12. (a) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem. 1995, 107, 2197-2181.
13. (b) Schwab, P.; France, M. B.; Ziller, J. W.; Grubbs, R. H. Angew. Chem., Int. Ed. Engl. 1995, 34, 2039-2041.
14. (c) Schwab, P.; Grubbs, R. H.; Ziller, J. W. J. Am. Chem. Soc. 1996, 118, 100-110.
15. (a) Fu, G. C.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 9856-9857.
16. (b) Clark, T. D.; Ghadiri, M. R. J. Am. Chem. Soc. 1995, 117, 12364-12365.
17. (c) Diver, S. T.; Schreiber, S. L. J. Am. Chem. Soc. 1997, 119, 5106-5109.
18. (a) Nguyen, S. T.; Grubbs, R. H. J. Organomet. Chem. 1995, 497, 195-200.
19. (b) Hartley, F. R. In Supported Metal Complexes; Ugo, R., James, B. R., Eds.; D. Reidel Publishing Company: Dordrecht, Holland, 1985.
20. (a) Mohr, B.; Lynn, D. M.; Grubbs, R. H. Organometallics 1996, 15, 4317-4325.
21. (b) Lynn, D. M.; Kanaoka, S.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 784-790.
22. For the detailed mechanism and activity of these catalysts, see: Dias, E. L.; Nguyen, S. T.; Grubbs, R. H. J. Am. Chem. Soc. 1997, 119, 3887-3897.
23. (a) Blaser, H.-U. Chem. Rev. 1992, 92, 935-952.
24. (b) Nitta, H.; Yu, D.; Kudo, M.; Mori, A.; Inoue, S. J. Am. Chem. Soc. 1992, 114, 7969-7975.
25. (c) El-Hendawy, A. M.; Alkybaisi, A. H.; El-Kourasy, A. E.-G.; Shanab, M. M. Polyhedron 1993, 12, 2343-2350.
26. (d) Herrmann, W. A.; Cornils, B. Angew. Chem., Int. Ed. Engl. 1997, 36, 1048-1067.
27. For recent examples of chiral ruthenium Schiff-base complexes in asymmetric reactions, see: (a) Kurseshy, R. I.; Khan, N. H.; Abdi, S. H. R.; Bhatt, K. N. Tetrahedron: Asymmetry 1993, 4, 1693-1701. (b) Chuard, T.; Gretillat, F.; Bernauer, K. Chimia 1993, 47, 215-217. (c) Kurseshy, R. I.; Khan, N. H.; Abdi, S. H. R.; Bhatt, A. K. J. Mol. Catal. A 1997, 120, 101-108.
28. For recent examples of chiral ruthenium Schiff-base complexes in asymmetric reactions, see: (a) Kurseshy, R. I.; Khan, N. H.; Abdi, S. H. R.; Bhatt, K. N. Tetrahedron: Asymmetry 1993, 4, 1693-1701. (b) Chuard, T.; Gretillat, F.; Bernauer, K. Chimia 1993, 47, 215-217. (c) Kurseshy, R. I.; Khan, N. H.; Abdi, S. H. R.; Bhatt, A. K. J. Mol. Catal. A 1997, 120, 101-108.
29. For recent examples of chiral ruthenium Schiff-base complexes in asymmetric reactions, see: (a) Kurseshy, R. I.; Khan, N. H.; Abdi, S. H. R.; Bhatt, K. N. Tetrahedron: Asymmetry 1993, 4, 1693-1701. (b) Chuard, T.; Gretillat, F.; Bernauer, K. Chimia 1993, 47, 215-217. (c) Kurseshy, R. I.; Khan, N. H.; Abdi, S. H. R.; Bhatt, A. K. J. Mol. Catal. A 1997, 120, 101-108.
30. Miller, S. J.; Blackwell, H. E.; Grubbs, R. H. J. Am. Chem. Soc. 1996, 118, 9606-9614.
31. Tallarico, J. A.; Bonitatebus, P. P. J.; Snapper, M. L. J. Am. Chem. Soc. 1997, 119, 7157-7158.
32. Esteruelas, M. A.; Lahoz, F. J.; Onate, E.; Oro, L. A.; Zeier, B. Organometallics 1994, 13, 4258-4265.
33. Pangborn, A. B.; Giardello, M. A.; Grubbs, R. H.; Rosen, R. K.; Timmers, F. J. Organometallics 1996, 15, 1518-1520.
34. Sone, T.; Katada, S.; Okiyoshi, Y.; Shinkai, S.; Manabe, O. Nippon Kagaku Kaishi 1982, 7, 1237-1240.
35. 3-Methyl-5-nitrosalicylaldehyde was prepared in the following manner. o-Cresol was treated with anhydrous stannic chloride, paraformaldehyde, 2,6-lutidine, and toluene to afford 3-methylsalicylaldehyde in 40% yield. The corresponding aldehyde was then nitrated using glacial acetic acid and concentrated nitric acid to afford the title compound in 97% yield.
36. 2,6-Diisopropyl-4-nitrobenzene was prepared in an analogous manner to that found in Wepster, B. M. Recl. Trav. Chim. 1954, 73, 809-818. 2,6-Diisopropylaniline was protected as the sulfonamide using tosyl chloride, pyridine, and dichloromethane in 97% yield. The corresponding sulfonamide was then nitrated using concentrated nitric acid, water, acetic anhydride, and sodium nitrite in 53% yield. Deprotection of the amine was accomplished using a 10:1 mixture of concentrated sulfuric acid:water to afford the title compound in quantitative yields.