The catalytic Pauson-Khand reaction promoted by a small amount of 1,2-dimethoxyethane or water

Synlett

Volumn , Issue 12, 1998, Pages 1384-1386

  Sugihara, Takumichi ^a,b   Yamaguchi, Masahiko ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b TOKUSHIMA BUNRI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000515507     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1991     Document Type: Article

References (39)

1. (a) Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E. J. Chem. Soc., Chem. Commun. 1971, 36.
2. (b) Khand, I. U.; Knox, G. R.; Pauson, P. L.; Watts, W. E.; Foreman, M. I. J. Chem. Soc., Perkin Trans. 1, 1973, 977.
3. For recent reviews, see; (a) Pauson, P. L. In Organometallics in Organic Synthesis; de Meijere, A.; tom Dieck, H. Eds.; Springer-Verlag: Berlin, 1987, p. 233.
4. (b) Shore, N. E. Chem. Rev. 1988, 88, 1081.
5. (c) Shore, N. E. In Organic Reaction, Vol. 40; Paquette, L. A. Ed.; John Wiley & Sons, Inc.: New York, 1991, p. 1.
6. (d) Shore, N. E. In Comprehensive Organic Synthesis, Vol. 5; Trost, B. M.; Fleming, I. Eds.; Pergamon: Oxford, 1991, p. 1037.
7. (e) Shore, N. E. In Comprehensive Organometallic Chemistry II, Vol. 12; Abel, E. W.; Stone, F. G. A.; Wilkinson, G. Eds.; Elsevier: New York, 1995, p. 703.
8. (f) Geis, O.; Schmalz, H.-G. Angew. Chem. 1998, 110, 955;
9. Angew. Chem., Int. Ed. Engl. 1998, 37, 911.
10. Leading references for applications to the synthesis of natural products, see; (a) Billington, D. C.; Pauson, P. L. Organometallics, 1982, 1, 5861.
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12. (c) Schore, N. E.; Rowley, E. G. J. Am. Chem. Soc. 1988, 110, 5224.
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17. 8, see; (a) Rautenstrauch, V.; Megard, P.; Conesa, J.; Küster, W. Angew. Chem. 1990, 102, 1441;
18. Angew. Chem., Int. Ed. Engl. 1990, 29, 1413.
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21. (d) Belanger, D. B.; O'Mahony, D. J. R.; Livinghouse, T. Tetrahedron Lett. 1998, 7637.
22. For other catalysts for the Pauson-Khand type cyclization, see: For Ti: Hicks, F. A.; Kablaoui, N. M.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 9450.
23. Hicks, F. A.; Buchwald, S. L. J. Am. Chem. Soc. 1996, 118, 11688.
24. For Ru: Morimoto, T.; Chatani, N.; Fukumoto, Y.; Murai, S. J. Org. Chem. 1997, 62, 3762.
25. Kondo, T.; Suzuki, N.; Okada, T.; Mitsudo, T. J. Am. Chem. Soc. 1997, 119, 6187.
26. For Rh: Koga, Y.; Kobayashi, T.; Narasaka, K. Chem. Lett. 1998, 249.
27. Jeong, N.; Lee, S.; Sung, B. K. Organometallics, 1998, 17, 3642.
28. For instance, see; Lukehart, C. M. Fundamental Transition Metal Organometallic Chemistry; Brooks/Cole: Monterey, 1985.
29. 3(arene)] complexes. See: Mahaffy, C. A. L.; Pauson, P. L.; Inorg. Synth. 1979, 19, 155.
30. Sugihara, T.; Yamada, M.; Ban, H.; Yamaguchi, M.; Kaneko, C. Angew. Chem. 1997, 109, 2884;
31. Angew. Chem., Int. Ed. Engl. 1997, 36, 2801.
32. (a) Gilmont, P.; Balanchard, A. A. Inorg. Synth. 1946, 2, 238.
33. (b) Devasagayaraj, A.; Periasamy, M. Tetrahedron Lett. 1989, 30, 595.
34. Dicobalt octacarbonyl was used as a freshly-prepared solution in toluene after sublimation. Since purity of dicobalt octacarbonyl largely influenced its catalytic activity, we recommend to use the complexes right after purification.
35. The use of the old stock solution of the catalyst in toluene sometimes gave better results than that of the freshly prepared solution. Standing the solution for a while might permit contamination of water and/or air to afford more reactive catalyst in such cases.
36. Since dicobalt octacarbonyl is known to react with "hard" ligands to produce cationic and anionic complexes via redox process, an excess amount of additives having more nucleophilic nature might promote the decomposition of dicobalt octacarbonyl prior to mediate the cyclization. For instance, see; Heiber, W.; Sedlmeier, J.; Abeck, W. Chem. Ber. 1953, 86, 700.
37. When 1a was treated with 0.2 molar equivalent of dicobalt octacarbonyl in 1,2-dimethoxy ethane at 25 °C under 7 atm of carbon monoxide, the alkyne-dicobalt hexacarbonyl complex of 1a was produced in 90% yield based on the cobalt complex. At lower temperature, an excess amount of 1,2-dimethoxy ethane did not decompose dicobalt octacarbonyl but promoted ligand exchange reaction on the cobalt.
38. 8 in 1,2-dimethoxyethane at limited range of temperature. See: ref. (4d).
39. 6 complexes as a catalyst, it could not be reproduced by the authors. The contamination of water might be one of the reasons for the unreproducibility. See: ref. (4a).