Pauson-Khand reactions using substoichiometric amounts of Co2(CO)8 under a nitrogen atmosphere

Synlett

Volumn , Issue 7, 2000, Pages 959-962

  Krafft, Marie E ^a   Boñaga, Llorente V R ^a  

^a FLORIDA STATE UNIVERSITY   (United States)

Author keywords

Cycloaddition; Cyclopentenone; Dicobalt octacarbonyl; Enyne; Pauson Khand

Indexed keywords

ARTICLE; ATMOSPHERE; CATALYST; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; STOICHIOMETRY;

EID: 0038798985     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (30)

1. For reviews, see: (a) Pauson, P. L. Tetrahedron 1985, 41, 5855.
2. (b) Pauson, P. L. In Organometallics in Organic Synthesis, Aspects of A Modern Interdisciplinary Field; de Meijere, A.; tom Dieck, H., Eds.; Springer-Verlag: Berlin 1988, p. 233.
3. (c) Schore, N. E. Chem. Rev. 1988, 88, 1081.
4. (d) Schore, N. E. Org. React. 1991, 40, 1.
5. (e) Schore, N. E. In Comprehensive Organic Synthesis, Vol. 5, Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford 1991, p. 1037.
6. (f) Schore, N. E. In Comprehensive Organometallic Chemistry II, Vol. 12, Abel, E. W.; Stone, F. A.; Wilkinson, G., Eds.; Elsevier: New York 1995, p. 703.
7. (g) Geis, O.; Schmalz, H. G. Angew. Chem., Int. Ed. Engl. 1998, 37, 911.
8. (h) Ingate, S. T.; Marco-Contellas, J. Org. Prep. Proceed. Int. 1998, 30, 123.
9. (i) Chung, Y. K. Coordination Chem. Rev. 1999, 188, 297. Hiroi, K.; Watanabe, T.; Kawagishi, R.; Abe, I. Tetrahedron Lett. 2000, 41, 891.
10. (i) Chung, Y. K. Coordination Chem. Rev. 1999, 188, 297. Hiroi, K.; Watanabe, T.; Kawagishi, R.; Abe, I. Tetrahedron Lett. 2000, 41, 891.
11. (a) Krafft, M. E.; Bonaga, L. V. R.; Hirosawa, C. Tetrahedron Lett. 1999, 40, 9171.
12. (b) Krafft, M. E.; Hirosawa, C.; Bonaga, L. V. R. Tetrahedron Lett. 1999, 40, 9177.
13. Schore, N. E.; Synth. Commun. 1979, 9, 41.
14. Entries 1-4, 6-8: Ref 2a, Entry 5: Krafft, M. E.; Wilson, A. M.; Dasse, O. A.; Shao, B.; Cheung, Y. Y.; Fu, Z.; Bonaga, L. V. R.; Mollman, M. K. J. Am. Chem. Soc. 1996, 118, 6080.
15. (a) Sugihara, T.; Yamada, M.; Ban, H.; Yamaguchi, M.; Kaneko, C. Angew. Chem., Int. Ed. Engl. 1997, 36, 2801. For reviews on the utility of Lewis bases in the Pauson-Khand reaction, see:
16. (b) Sugihara, T.; Yamaguchi, M.; Nishizawa, M. Recent Res. Devel. Organometallic Chem. 1999, 2, 13.
17. (c) Sugihara, T.; Yamaguchi, M.; Nishizawa, M. Rev. Heteroatom Chem. 1999, 21, 179.
18. Rajesh, T.; Periasamy, M. Tetrahedron Lett. 1998, 39, 117.
19. Belanger, D. B.; Livinghouse, T. Tetrahedron Lett. 1998, 39, 7641.
20. (a) Belanger, D. B.; O'Mahoney, D. J. R.; Livinghouse, T. Tetrahedron Lett. 1998, 39, 7637.
21. (b) Lee, B. Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 8793.
22. (c) Lee, B. Y.; Chung, Y. K. Tetrahedron Lett. 1996, 37, 3145.
23. (d) Pagenkopf, B. L.; Livinghouse, T. J. Am. Chem. Soc. 1996, 118, 2285.
24. Sugihara, T.; Yamaguchi, M. Synlett 1998, 1384.
25. 7
26. 2 in stoichiometric Pauson-Khand reactions carried out in dichloroethane under argon was first demonstrated by Sugihara - see reference 5a.
27. (a) nbutyl methyl sulfide, thioanisole: Sugihara, T.; Yamada, M.; Yamaguchi, M; Mishizawa, M. Synlett 1999, 771.
28. (b) thiophene: reference 7.
29. (c) triphenylphosphite: Jeong, N.; Hwang, S. H.; Lee, Y.; Chung, Y. K. J. Am. Chem. Soc. 1994, 116, 3159.
30. Wender, I.; Sternberg, H. W.; Orchin, M. J. Am. Chem. Soc. 1952, 74, 1216.