Carbonyl olefination using readily prepared tungsten metallacycles

Inorganic Chemistry

Volumn 47, Issue 23, 2008, Pages 11191-11196

  Lokare, Kapil S ^a   Odom, Aaron L ^a  

^a MICHIGAN STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 57949085080     PISSN: 00201669     EISSN: None     Source Type: Journal    
DOI: 10.1021/ic8014964     Document Type: Article

References (36)

1. Nugent, W. A.; Mayer, J. M. Metal-Ligand Multiple Bonds; John Wiley & Sons: New York, 1988.
2. (a) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Chichester, 2003.
3. (b) Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic Press, San Diego, 1997.
4. (c) Schrock, R. R. J. Mol. Catal. A: Chem. 2004, 213, 21-30.
5. (d) Schrock, R. R.; Hoveyda, A. H. Angew. Chem., Int. Ed. 2003, 42, 4592-4633.
6. (e) Schrock, R. R. Angew. Chem., Int. Ed. 2006, 45, 3748-3759.
7. For some seminal papers on tungsten alkylidenes including Wittig-like reactions see (a) Aguero, A.; Kress, J.; Osborn, J. A. Chem. Commun. 1986, 531.
8. (b) Kress, J.; Osborn, J. A. J. Am. Chem. Soc. 1987, 109, 3953.
9. (c) Kress, J.; Osborn, J. A. Angew. Chem., Int. Ed. 1992, 31, 1585.
10. Fu, G. C.; Grubbs, R. H. J. Am. Chem. Soc. 1993, 115, 3800.
11. For seminal references on the Tebbe reagent see (a) Tebbe, F. N.; Parshall, G. W.; Reddy, G. S. J. Am. Chem. Soc. 1978, 100, 3611.
12. (b) Tebbe, F. N.; Parshall, G. W.; Ovenall, D. W. J. Am. Chem. Soc. 1979, 101, 5074.
13. (c) Krusic, P. J.; Tebbe, F. N. Inorg. Chem. 1982, 21, 2900.
14. For some recent titanium-mediated carbonyl methylenation examples see (a) Iyer, K.; Rainier, J. D. J. Am. Chem. Soc. 2007, 129, 12604.
15. (b) Donohoe, T. J.; Fishlock, L. P.; Lacy, A. R.; Procopiou, P. A. Org. Lett. 2007, 9, 953.
16. (c) Bennasar, M. L.; Roca, T.; Monerris, M.; Garcia-Diaz, D. J. Org. Chem. 2006, 71, 7028.
17. (d) Johnson, H. W. B.; Majumder, U.; Rainier, J. D. J. Am. Chem. Soc. 2005, 127, 848.
18. (e) Kadota, I.; Takamura, H.; Sato, K.; Ohno, A.; Matsuda, K.; Satake, M.; Yamamoto, Y. J. Am. Chem. Soc. 2003, 125, 11893.
19. (f) Nicolaou, K. C.; Postema, M. H. D.; Yue, E. W.; Nadin, A. J. Am. Chem. Soc. 1996, 118, 10335.
20. (g) Majumder, U.; Rainier, J. D. Tetrahedron Lett. 2005, 46, 7209.
21. For a recent review see Hartley, R. C.; Li, J.; Main, C. A.; McKiernan, G. J. Tetrahedron 2007, 63, 4825.
22. Lokare, K. S.; Ciszewski, J. T.; Odom, A. L. Organometallics 2004, 23, 5386.
23. Schrock, R. R.; Mudzek, J. S.; Bazan, G. C.; Robbins, J.; DiMare, M.; O'Regan, M. B. J. Am. Chem. Soc. 1990, 112, 3875.
24. Brandsma, L.; Verkruijsse, H. D. Synthesis 1978, 290.
25. Typical C-N bond distance from (a) Gordon, A. J.; Ford, R. A. The Chemist's Companion; John Wiley & Sons: New York, 1972. C=N distance taken from.
26. 2 because of similar steric effects to our case and electronically isolated imine bond.
27. Zhu, J.; Jia, G.; Lin, Z. Organometallics 2007, 26, 1986.
28. For a recent alternative synthesis of 2-phenyl-4,5-dihydrofuran 7b by decarbonylative ring expansion of a cyclopropanyl carboxylic acid see (a) Jahngen, E.; Mallett, J.; O'Connor, R.; Fischer, S. Arkivoc 2007, 135.
29. For a recently reported alternative synthesis of compound 7c by hydrolysis of phenyl cyclopropanyl ketone see (a) Yang, Y.-H.; Shi, M. J. Org. Chem. 2005, 70, 10082; Several other methodologies have been applied to its synthesis.
30. Schrock, R. R.; DePue, R. T.; Feldman, J.; Schaverien, C. J.; Dewan, J. C.; Liu, A. H. J. Am. Chem. Soc. 1988, 110, 1423.
31. Fox, H. H.; Lee, J.; Park, L. Y.; Schrock, R. R. Organometallics 1993, 12, 759.
32. (a) Zechmann, C. A.; Boyle, T. J.; Pedrotty, D. M. Inorg. Chem. 2001, 40, 2177-2184.
33. (b) Childress, M. V.; Millar, D.; Alam, T. M.; Kreisel, K. A.; Yap, G. P. A.; Zakharov, L. N.; Golen, J. A.; Rheingold, A. L.; Doerrer, L. H. Inorg. Chem. 2006, 45, 3864-3877.
34. Yakelis, N. A.; Bergman, R. G. Organometallics 2005, 24, 3579.
35. For instability of similar furans see: (a) Betancourt de Perez, R. M.; Fuentes, L. M.; Larson, G. L.; Barnes, C. L.; Heeg, M. J. J. Org. Chem. 1986, 51, 2039-2043.
36. (b) Lehmann, U.; Awasthi, S.; Minehan, T. Org. Lett. 2003, 5, 2405-2408.