Activation of alkyne-dicobalt hexacarbonyl complexes by the Lewis bases - A new trend in the Pauson-Khand reaction

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 57, Issue 3, 1999, Pages 158-169

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

^a TOKUSHIMA BUNRI UNIVERSITY   (Japan)

^b TOHOKU UNIVERSITY   (Japan)

Author keywords

Alkyne dicobalt hexacarbonyl complex; Amine; Catalytic cyclization; Decomplexation; Hydrocarbamoylation; Pauson Khand reaction; Sulfide; Water

Indexed keywords

EID: 0004958224     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.57.158     Document Type: Article

References (58)

1. R.D.W. Kemmitt, D.R. Russell, "Comprehensive Organometallic Chemistry", ed. by G. Wilkinson, F.G.A. Stone, E.W. Abel, Pergamon Press, Oxford, 1982, Vol.5, p.1
2. S.G. Davis, "Organotransition Metal Chemistry: Applications to Organic Synthesis", Pergamon Press, Oxford, 1986, pp.86-90;
3. H. Kunz, H. Waldmann, "Comprehensive Organometallic Chemistry II", ed. by E.W. Abel, F.G.A. Stone, G. Wilkinson, Elsevier, New York, 1995, Vol.6, pp.692-693
4. K.M. Nicholas, Acc. Chem. Res., 20, 207 (1987);
5. A.J.M. Caffyn, K.M. Nicholas, "Comprehensive Organometallic Chemistry II", ed. by E.W. Abel, F.G.A. Stone, G. Wilkinson, Elsevier, New York, 1995, Vol.12, pp.685-702
6. P.L. Pauson, "Organometallics in Organic Synthesis", ed. by A. de Meijere, H. tom Dieck, Springer-Verlag, Berlin, 1987, pp. 233-246;
7. N.E. Shore, Chem. Rev., 88, 1081 (1988);
8. N.E. Shore, Org. React., 40, 1 (1991);
9. N.E. Shore, "Comprehensive Organic Synthesis", ed. by B.M. Trost, I. Fleming, Pergamon, Oxford, 1991, Vol.5, pp.1037-1064;
10. N.E. Shore, "Comprehensive Organometallic Chemistry II", ed. by E.W. Abel, F.G.A. Stone, G. Wilkinson, Elsevier, New York, 1995, Vol.12, pp.703-739
11. R.J. Dennenberg, D.J. Darensbourg, Inorg. Chem., 11, 72 (1972);
12. D.J. Darensbourg, R.L. Kump, Inorg. Chem., ibid., 17, 2680 (1978)
13. B.E. La Belle, M.J. Knudsen, M.M. Olmstead, H. Hope, M.D. Yanuck, N.E. Schore, J. Org. Chem., 50, 5215 (1985)
14. S. Shambayati, W.E. Crowe, S.L. Schreiber, Tetrahedron Lett, 31, 5289 (1990);
15. N. Jeong, Y. K. Chung, B.Y. Lee, S.H. Lee, S.-E. Yoo, Synlett, 1991, 204
16. T. Sugihara, M. Yamada, H. Ban, M. Yamaguchi, C. Kaneko, Angew. Chem., Int. Ed. Engl., 36, 2801 (1997)
17. N. Iwasawa, T. Matsuo, Chem. Lett., 1997, 341
18. E. Negishi, S.E. Holmes, J.M. Tour, J.A. Miller, J. Am. Chem. Soc., 107, 2568 (1985);
19. K. Tamao, K. Kobayashi, Y. Ito, J. Am. Chem. Soc., ibid., 110, 1286 (1988);
20. E. Negishi, S.E. Holmes, J.M. Tour, J.A. Miller, F.E. Cederbaum, D.R. Swanson, T. Takahashi, J. Am. Chem. Soc., ibid., 111, 3336 (1989);
21. V. Rautenstrauch, P. Megard, J. Conesa, W. Küster, Angew. Chem., Int. Ed. Engl., 29, 1413 (1990);
22. A.J. Pearson, R.A. Dubbert, J. Chem. Soc., Chem. Commun., 1991, 202;
23. K. Tamao, K. Kobayashi, Y. Ito, Synlett, 1992, 539;
24. C. Mukai, M. Uchiyama, M. Hanaoka, J. Chem. Soc., Chem. Commun., 1992, 1014;
25. R.B. Grossman, S.L. Buchwald, J. Org. Chem., 57, 5803 (1992);
26. T.R. Hoye, J. A. Suriano, Organometallics, 11, 2044 (1992);
27. S.C. Berk, R.B. Grossman, S.L. Buchwald, J. Am. Chem. Soc., 115, 4912 (1993);
28. T.R. Hoye, J.A. Suriano, J. Am. Chem. Soc., ibid., 115, 1154 (1993);
29. N. Jeong, S.J. Lee, B.Y. Lee, Y.K. Chung, Tetrahedron Lett., 34, 4027 (1993);
30. L. Jordi, A. Segundo, F. Camps, S. Ricart, J.M. Moreto, Organometallics, 12, 3795 (1993);
31. S.C. Berk, R. B. Grossman, S. L. Buchwald, J. Am. Chem. Soc., 116, 8593 (1994);
32. A.J. Peason, R. A. Dubbert, Organometallics, 13, 1656 (1994);
33. J.L. Kent, H. Wan, K.M. Brummond, Tetrahedron Lett., 36, 2407 (1995);
34. F. Hicks, N.M. Kablaoui, S.L. Buchwald, J. Am. Chem. Soc., 118, 9450 (1996);
35. M. Zhang, S.L. Buchwald, J. Org. Chem. 61, 4498 (1996);
36. T. Morimoto, N. Chatani, Y. Fukumoto, S. Murai, J. Org. Chem. ibid., 62, 3762 (1997);
37. T. Kondo, N. Suzuki, T. Okada, T. Mitsudo, J. Am. Chem. Soc., 119, 6187 (1997);
38. Y. Koga, T. Kobayashi, K. Narasaka, Chem. Lett., 1998, 249
39. T. Sugihara, M. Yamaguchi, unpublished results.
40. P. Bladon, P.L. Pauson, H. Brunner, R. Eder, J. Organomet. Chem., 355, 449 (1988)
41. M.E. Krafft, I.L. Scott, R.H. Romero, S. Feibelmann, C.E. Van Pelt, J. Am. Chem. Soc., 115, 7199 (1993)
42. T. Sugihara, M. Yamada, M. Yamaguchi, M. Nishizawa, unpublished results.
43. D. Seyferth, M.O. Nestle, A.T. Wehman, J. Am. Chem. Soc., 97, 7417 (1975);
44. C. Descoins, D. Samain, Tetrahedron Lett., 1976, 745;
45. J.E. O'Boyle, K.M. Nicholas, Tetrahedron Lett., ibid., 21, 1595 (1980);
46. K.M. Nicholas, M. Mulvaney, M. Bayer, J. Am. Chem. Soc., 102, 2508 (1980)
47. M. Isobe, C. Yenjai, S. Tanaka, Synlett. 1994, 916;
48. S. Hosokawa, M. Isobe, Synlett. ibid., 1995, 1179;
49. T. Nakamura, T. Matsui, K. Tanino, I. Kuwajima, J. Org. Chem., 62, 3032 (1997)
50. T. Sugihara, H. Ban, M. Yamaguchi, J. Organomet. Chem., 554, 163 (1998)
51. T. Sugihara, M. Yamaguchi, unpublished results.
52. P. Gilmont, A.A. Balanchard, Inorg. Synth., 2, 238 (1946);
53. A. Devasagayaraj, M. Periassamy, Tetrahedron Lett., 30, 595 (1989)
54. T. Sugihara, M. Yamaguchi, Synlett, 1998, 1384
55. N. Jeong, S.H. Hwang, Y. Lee, Y.K. Chung, J. Am. Chem. Soc., 116, 3159 (1994);
56. B.L. Pagenkopf, T. Livinghouse, J. Am. Chem. Soc., ibid., 118, 2285 (1996)
57. W. Heiber, J. Sedlmeier, W. Abeck, Chem. Ber., 86, 700 (1953)
58. D.B. Belanger, D.J.R. O'Mahony, T. Livinghouse, Tetrahedron Lett., 39, 7637 (1998)