Diverse reactivity manifolds of alkynyl enone- and alkynyl enal-derived nickelacycles discovery of nickel-promoted [3+2] and [2+1] cycloadditions [6]

Journal of the American Chemical Society

Volumn 122, Issue 28, 2000, Pages 6775-6776

  Chowdhury, Sanjoy K ^a   Amarasinghe, Kande K D ^a   Heeg, Mary Jane ^a   Montgomery, John ^a  

^a WAYNE STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL REACTION KINETICS; CYCLIZATION; DIMERIZATION; LETTER; ORGANIC CHEMISTRY; OXIDATIVE STRESS; STOICHIOMETRY; STRUCTURE ANALYSIS;

EID: 0034686737     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja0012624     Document Type: Letter

References (23)

1. Montgomery, J. Acc. Chem. Res. 2000, in press.
2. (a) Montgomery, J.; Savchenko, A. V. J. Am. Chem. Soc. 1996, 118, 2099-2100.
3. (b) Montgomery, J.; Oblinger, E.; Savchenko, A. V. J. Am. Chem. Soc. 1997, 119, 4911-4920.
4. (c) Chevliakov, M. V.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 11139.
5. For related work from Ikeda and Sato, see: (a) Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1994, 116, 5975-5976. (b) Ikeda, S.; Yamamoto, H.; Kondo, K.; Sato, Y. Organometallics 1995, 14, 5015-5016. Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248-8255. Ikeda, S.; Mori, N.; Sato, Y. J. Am. Chem. Soc. 1997, 119, 4779-4780.
6. For related work from Ikeda and Sato, see: (a) Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1994, 116, 5975-5976. (b) Ikeda, S.; Yamamoto, H.; Kondo, K.; Sato, Y. Organometallics 1995, 14, 5015-5016. Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248-8255. Ikeda, S.; Mori, N.; Sato, Y. J. Am. Chem. Soc. 1997, 119, 4779-4780.
7. For related work from Ikeda and Sato, see: (a) Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1994, 116, 5975-5976. (b) Ikeda, S.; Yamamoto, H.; Kondo, K.; Sato, Y. Organometallics 1995, 14, 5015-5016. Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248-8255. Ikeda, S.; Mori, N.; Sato, Y. J. Am. Chem. Soc. 1997, 119, 4779-4780.
8. For related work from Ikeda and Sato, see: (a) Ikeda, S.; Sato, Y. J. Am. Chem. Soc. 1994, 116, 5975-5976. (b) Ikeda, S.; Yamamoto, H.; Kondo, K.; Sato, Y. Organometallics 1995, 14, 5015-5016. Ikeda, S.; Kondo, K.; Sato, Y. J. Org. Chem. 1996, 61, 8248-8255. Ikeda, S.; Mori, N.; Sato, Y. J. Am. Chem. Soc. 1997, 119, 4779-4780.
9. Seo, J.; Chui, H. M. P.; Heeg, M. J.; Montgomery, J. J. Am. Chem. Soc. 1999, 121, 476-477.
10. For leading references to nickel metallacycles, see: (a) Grubbs, R. H.; Miyashita, A.; Liu, M. M.; Burk, P. L. J. Am. Chem. Soc. 1977, 99, 3863-3864. (b) Grubbs, R. H.; Miyashita, A. J. Am. Chem. Soc. 1978, 100, 1300- 1302.
11. For leading references to nickel metallacycles, see: (a) Grubbs, R. H.; Miyashita, A.; Liu, M. M.; Burk, P. L. J. Am. Chem. Soc. 1977, 99, 3863- 3864. (b) Grubbs, R. H.; Miyashita, A. J. Am. Chem. Soc. 1978, 100, 1300-1302.
12. Related titanium-promoted [3+2] cycloadditions of enoate/alkyne precursors have been reported, (a) Suzuki, K.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 1996, 118, 8729. (b) Urabe, H.; Suzuki, K.; Sato, F. J. Am. Chem. Soc. 1997, 119, 10014.
13. Related titanium-promoted [3+2] cycloadditions of enoate/alkyne precursors have been reported, (a) Suzuki, K.; Urabe, H.; Sato, F. J. Am. Chem. Soc. 1996, 118, 8729. (b) Urabe, H.; Suzuki, K.; Sato, F. J. Am. Chem. Soc. 1997, 119, 10014.
14. For transition metal-catalyzed reductive aldols of enones, see: Taylor, S. J.; Morken, J. P. J. Am. Chem. Soc. 1999, 121, 12202.
15. Burkhardt, E. R.; Bergman, R. G.; Heathcock, C. H. Organometallics 1990, 9, 30-44.
16. (a) Evans, D. A.; Hoveyda, A. H. J. Am. Chem. Soc. 1990, 112, 6447.
17. (b) Bodnar, P. M.; Shaw, J. T.; Woerpel, K. A. J. Org. Chem. 1997, 62, 5674.
18. Parallels to this reaction are found in the work of Sato involving titanium-promoted cyclizations of electron-deficient enynes. In contrast to our studies which require oxidation to promote cyclopropane formation, titanium metallacycles derived from ynoates undergo thermal rearrangement to titanium carbenes without oxygen atom introduction. See ref 6. A rearrangement of a rhenium metallacyclopentane to a cyclopropane has also been reported: Yang, G. K.; Bergman, R. G. Organometallics 1985, 4, 129.
19. For studies involving the oxidation of nickel metallacycles, see: (a) Matsunaga, P. T.; Hillhouse, G. L.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 2075. (b) Koo, K. M.; Hillhouse, G. L.; Rheingold, A. L. Organometallics 1995, 14, 456.
20. For studies involving the oxidation of nickel metallacycles, see: (a) Matsunaga, P. T.; Hillhouse, G. L.; Rheingold, A. L. J. Am. Chem. Soc. 1993, 115, 2075. (b) Koo, K. M.; Hillhouse, G. L.; Rheingold, A. L. Organometallics 1995, 14, 456.
21. For leading references to nickel carbene species, see: Herrmann, W. A.; Gerstberger, G.; Spiegler, M. Organometallics 1997, 16, 2209.
22. (b) Douthwaite, R. E.; Haüssinger, D.; Green, M. L. H.; Silcock, P. J.; Gomes, P. T.; Martins, A. M.; Danopoulos, A. A. Organometallics 1999, 18, 4584.
23. (c) Eisch, J. J.; Aradi, A. A.; Lucarelli, M. A.; Qian, Y. Tetrahedron 1998, 54, 1169.