Oxidatively induced carbonylation and cyclization of ruthenium(II) vinyl-olefin complexes prepared via allyl/alkyne coupling

Organometallics

Volumn 19, Issue 17, 2000, Pages 3266-3268

  Older, Christina M ^a   Stryker, Jeffrey M ^a  

^a UNIVERSITY OF ALBERTA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON MONOXIDE; CARBONYLATION; COMPLEXATION; OLEFINS; OXIDATION; PARAFFINS;

CYCLIZATION; DICHLOROMETHANE; PENTADIENE;

ORGANOMETALLICS;

EID: 0034246940     PISSN: 02767333     EISSN: None     Source Type: Journal    
DOI: 10.1021/om000407c     Document Type: Article

References (54)

1. Reviews: (a) Kochi, J. K. Organometallic Mechanisms and Catalysis; Academic Press: New York, 1978.
2. (b) Baird, M. C. Chem. Rev. 1988, 88, 1217.
3. (c) Astruc, D. Chem. Rev. 1988, 88, 1216.
4. (d) Connelly, N. G. Chem. Soc. Rev. 1989, 18, 153.
5. (e) Trogler, W. C., ed. Organometallic Radical Processes; Elsevier Science: Amsterdam, 1990.
6. (f) Astruc, D. Acc. Chem. Res. 1991, 24, 36.
7. (g) Tyler, D. R. Acc. Chem. Res. 1991, 24, 325.
8. (h) Connelly, N. G.; Geiger, W. E. Chem. Rev. 1996, 96, 877.
9. Recent and lead references: (i) Legzdins, P.; McNeil, W. S.; Rettig, S. J.; Smith, K. M. J. Am. Chem. Soc. 1997, 119, 3513.
10. (j) Fooladi, E.; Tilset, M. Inorg. Chem. 1997, 36, 6021 and references therein.
11. (k) Shaw, M. J.; Geiger, W. E.; Hyde, J.; White, C. Organometallics 1998, 17, 5486.
12. (l) Bartlett, I. A.; Connelly, N. G.; Martin, A. J.; Orpen, A. G.; Paget, T. J.; Rieger, A. L.; Rieger, P. H. J. Chem. Soc., Dalton Trans. 1999, 691.
13. (m) Wolfbauer, G.; Bond, A. M.; MacFarlane, D. R. Inorg. Chem. 1999, 38, 3836.
14. Lead references to CO insertion in the 17e/19e manifold: (a) Bly, R. S.; Silverman, G. S.; Ely, R. K. Organometallics 1985, 4, 374.
15. (b) Therien, M. J.; Trogler, W. C. J. Am. Chem. Soc. 1987, 109, 5127 and references therein.
16. (c) Golovin, M. N.; Meirowitz, R. E.; Rahman, M. M.; Liu, H.-Y.; Prock, A.; Giering, W. P. Organometallics 1987, 6, 2285.
17. (d) Donovan, B. T.; Geiger, W. E. Organometallics 1990, 9, 865.
18. (e) Tracey, A. A.; Eriks, K.; Prock, A.; Giering, W. P. Organometallics 1990, 9, 1399.
19. (f) Prock, A.; Giering, W. P.; Greene, J. E.; Meirowitz, R. E.; Hoffman, S. L.; Woska, D. C.; Wilson, M.; Chang, R.; Chen, J.; Magnuson, R. H.; Eriks, K. Organometallics 1991, 10, 3479.
20. (a) Older, C. M.; Stryker, J. M. Organometallics 2000, 19, 2166.
21. 2-vinyl coordination, although the latter may be geometrically untenable.
22. Complete experimental and characterization data are provided as Supporting Information.
23. 5).
24. Other (1:4,5-η)-1,4-pentadien-1-yl complexes prepared by allyl/alkyne coupling: (a) Appleton, T. G.; Clark, H. C.; Poller, R. C.; Puddephatt, R. J. J. Organomet. Chem. 1972, 39, C13.
25. (b) Green, M.; Taylor, S. J. J. Chem. Soc., Dalton Trans. 1975, 1142.
26. (c) Bottrill, M.; Green, M.; O'Brien, E.; Smart, L. E.; Woodward, P. J. Chem. Soc., Dalton Trans. 1980, 292.
27. (d) Betz, P.; Jolly, P. W.; Kruger, C.; Zakrzewski, U. Organometallics 1991, 10, 3520.
28. (e) Schwiebert, K. E. Ph.D. Dissertation, Indiana University, 1993.
29. Siwapinyoyos, T.; Thebtaranonth, Y. J. Org. Chem. 1982, 47, 598.
30. Suzuki, N.; Kondakov, D. Y.; Kageyama, M.; Kotora, M.; Hara, R.; Takahashi, T. Tetrahedron 1995, 51, 4519.
31. Schwiebert, K. E.; Stryker, J. M. J. Am. Chem. Soc. 1994, 116, 11570.
32. The oxidation reaction in acetonitrile (no added carbon monoxide) was also carried out in the presence of excess alkyne or under an atmosphere of ethylene. No significant difference in the products or the product ratios was observed in these experiments compared to the products obtained from the reaction in acetonitrile alone.
33. The reported yield of 3b is considered to be a lower limit due to the volatility of this compound.
34. For recent and leading references to the total synthesis of methylenomycin B (3b), see ref 7 and the following: (a) Jernow, J.; Tautz, W.; Rosen, P.; Williams, T. H. J. Org. Chem. 1979, 44, 4212.
35. (b) Camps, F.; Coll, J.; Moretó, J. M.; Torras, J. Tetrahedron Lett. 1985, 26, 6397.
36. (c) Mikolajczyk, M.; Zatorski, A. J. Org. Chem. 1991, 56, 1217 and references therein.
37. (d) Mathew, J. J. Chem. Soc., Perkin Trans. 1 1991, 2039.
38. (e) Jacobi, P.; Brielmann, H. L.; Cann, R. O. J. Org. Chem. 1994, 59, 5305.
39. (f) Negishi, E. I.; Ma, S.; Amanfu, J.; Copéret, C.; Miller, J. A.; Tour, J. M. J. Am. Chem. Soc. 1996, 118, 5919.
40. (g) Balczewski, P. Tetrahedron 1997, 53, 2199.
41. +: Kulawiec, R. J.; Faller, J. W.; Crabtree, R. H. Organometallics 1990, 9, 745.
42. 1 Alternative, nondissociative, mechanisms are also possible, as suggested by a reviewer.
43. (a) Chiusoli, G. P.; Cassar, L. Angew. Chem., Int. Ed. Engl. 1967, 6, 124.
44. (b) Chiusoli, G. P. Acc. Chem. Res. 1973, 6, 422.
45. Wilke, G. Angew. Chem., Int. Ed. Engl. 1988, 27, 186.
46. (c) Billington, D. C. Chem. Soc. Rev. 1985, 93 and references therein.
47. (d) Camps, F.; Moretó, J. M.; Pagès, L. Tetrahedron 1992, 48, 3147.
48. Vilaseca, F.; Pagès, L.; Villar, J. M.; Llebaria, A.; Delgado, A.; Moretó, J. M. J. Organomet. Chem. 1998, 551, 107.
49. García-Gómez, G.; Moretó, J. M. J. Am. Chem. Soc. 1999, 121, 878.
50. 5 complexes: (a) McDade, C.; Brock, C. P.; Bercaw, J. E. Organometallics 1982, 1, 1629.
51. (b) Schock, L. E.; Brock, C. P.; Marks, T. J. Organometallics 1987, 6, 232.
52. (c) Koelle, U.; Kang, B.-S.; Thewalt, U. J. Organomet. Chem. 1990, 386, 267.
53. (d) Fan, L.; Wei, C.; Aigbirhio, F.; Turner, M. L.; Gusev, O. V.; Morozova, L. N.; Knowles, D. R. T.; Maitlis, P. M. Organometallics 1996, 15, 98.
54. Fan, L. Turner, M. L.; Hursthouse, M. B.; Malik, K. M. A. Gusev, O. V.; Maitlis, P. M. J. Am. Chem. Soc. 1994, 116, 385.