Rate Enhancement of the Pauson - Khand Reaction by Primary Amines

Angewandte Chemie (International Edition in English)

Volumn 36, Issue 24, 1997, Pages 2801-2804

  Sugihara, Takumichi ^a   Yamada, Mamiko ^a   Ban, Hitoshi ^a   Yamaguchi, Masahiko ^a   Kaneko, Chikara ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Alkyne complexes; Amines; Carbonyl complexes; Cobalt; Cyclization

Indexed keywords

EID: 0032491869     PISSN: 05700833     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.199728011     Document Type: Article

References (34)

1. a) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, J. Chem. Soc. Chem. Commun. 1971, 36;
2. b) I. U. Khand, G. R. Knox, P. L. Pauson, W. E. Watts, M. I. Foreman, J. Chem. Soc. Perkin Trans. 1 1973, 977;
3. c) P. L. Pauson, I. U. Khand, Ann. NY Acad. Sci. 1977, 295, 2;
4. d) P. L. Pauson, Tetrahedron 1985, 41, 5855.
5. For recent reviews, see; a) P.L. Pauson in Organometallics in Organic Synthesis (Eds.: A. de Meijere, H. tom Dieck), Springer, Berlin, 1987, p. 233; b) N. E. Shore, Chem. Rev. 1988, 88, 1081; c) N. E. Schore in Organic Reactions, Vol. 40 (Ed.: L. A. Paquette), Wiley, New York, 1991, p. 1; d) N. E. Schore in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon, Oxford, 1991, p. 1037; e) N. E. Schore in Comprehensive Organometallic Chemistry II, Vol. 12 (Ed.: E. W. Abel, F. G. Stone, G. Wilkinson), Elsevier, New York, 1995, p. 703.
6. For recent reviews, see; a) P.L. Pauson in Organometallics in Organic Synthesis (Eds.: A. de Meijere, H. tom Dieck), Springer, Berlin, 1987, p. 233; b) N. E. Shore, Chem. Rev. 1988, 88, 1081; c) N. E. Schore in Organic Reactions, Vol. 40 (Ed.: L. A. Paquette), Wiley, New York, 1991, p. 1; d) N. E. Schore in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon, Oxford, 1991, p. 1037; e) N. E. Schore in Comprehensive Organometallic Chemistry II, Vol. 12 (Ed.: E. W. Abel, F. G. Stone, G. Wilkinson), Elsevier, New York, 1995, p. 703.
7. For recent reviews, see; a) P.L. Pauson in Organometallics in Organic Synthesis (Eds.: A. de Meijere, H. tom Dieck), Springer, Berlin, 1987, p. 233; b) N. E. Shore, Chem. Rev. 1988, 88, 1081; c) N. E. Schore in Organic Reactions, Vol. 40 (Ed.: L. A. Paquette), Wiley, New York, 1991, p. 1; d) N. E. Schore in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon, Oxford, 1991, p. 1037; e) N. E. Schore in Comprehensive Organometallic Chemistry II, Vol. 12 (Ed.: E. W. Abel, F. G. Stone, G. Wilkinson), Elsevier, New York, 1995, p. 703.
8. For recent reviews, see; a) P.L. Pauson in Organometallics in Organic Synthesis (Eds.: A. de Meijere, H. tom Dieck), Springer, Berlin, 1987, p. 233; b) N. E. Shore, Chem. Rev. 1988, 88, 1081; c) N. E. Schore in Organic Reactions, Vol. 40 (Ed.: L. A. Paquette), Wiley, New York, 1991, p. 1; d) N. E. Schore in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon, Oxford, 1991, p. 1037; e) N. E. Schore in Comprehensive Organometallic Chemistry II, Vol. 12 (Ed.: E. W. Abel, F. G. Stone, G. Wilkinson), Elsevier, New York, 1995, p. 703.
9. For recent reviews, see; a) P.L. Pauson in Organometallics in Organic Synthesis (Eds.: A. de Meijere, H. tom Dieck), Springer, Berlin, 1987, p. 233; b) N. E. Shore, Chem. Rev. 1988, 88, 1081; c) N. E. Schore in Organic Reactions, Vol. 40 (Ed.: L. A. Paquette), Wiley, New York, 1991, p. 1; d) N. E. Schore in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon, Oxford, 1991, p. 1037; e) N. E. Schore in Comprehensive Organometallic Chemistry II, Vol. 12 (Ed.: E. W. Abel, F. G. Stone, G. Wilkinson), Elsevier, New York, 1995, p. 703.
10. Lading references for applications to the synthesis of natural products: a) D. C. Billington, P. L. Pauson, Organometallics 1982, 1, 5861; b) C. Exon, P. Magnus, J. Am. Chem. Soc. 1983, 105, 2477; c) N. E. Schore, E. G. Rowley, ibid. 1988, 110, 5224; d) S. Takano, K. Inomata, K. Ogasawara, J. Chem. Soc. Chem. Commun. 1992, 169; e) S. Takano, K. Inomata, K. Ogasawara, Chem. Lett. 1992, 443; f) S. Yoo, S.-H. Lee, N. Jeong, I. Cho, Tetrahedron Lett. 1993, 34, 3435; g) T. F. Jamison, S. Shambayati, W. E. Crowe, S. L. Schreiber, J. Am. Chem. Soc. 1994, 116, 5505.
11. Lading references for applications to the synthesis of natural products: a) D. C. Billington, P. L. Pauson, Organometallics 1982, 1, 5861; b) C. Exon, P. Magnus, J. Am. Chem. Soc. 1983, 105, 2477; c) N. E. Schore, E. G. Rowley, ibid. 1988, 110, 5224; d) S. Takano, K. Inomata, K. Ogasawara, J. Chem. Soc. Chem. Commun. 1992, 169; e) S. Takano, K. Inomata, K. Ogasawara, Chem. Lett. 1992, 443; f) S. Yoo, S.-H. Lee, N. Jeong, I. Cho, Tetrahedron Lett. 1993, 34, 3435; g) T. F. Jamison, S. Shambayati, W. E. Crowe, S. L. Schreiber, J. Am. Chem. Soc. 1994, 116, 5505.
12. Lading references for applications to the synthesis of natural products: a) D. C. Billington, P. L. Pauson, Organometallics 1982, 1, 5861; b) C. Exon, P. Magnus, J. Am. Chem. Soc. 1983, 105, 2477; c) N. E. Schore, E. G. Rowley, ibid. 1988, 110, 5224; d) S. Takano, K. Inomata, K. Ogasawara, J. Chem. Soc. Chem. Commun. 1992, 169; e) S. Takano, K. Inomata, K. Ogasawara, Chem. Lett. 1992, 443; f) S. Yoo, S.-H. Lee, N. Jeong, I. Cho, Tetrahedron Lett. 1993, 34, 3435; g) T. F. Jamison, S. Shambayati, W. E. Crowe, S. L. Schreiber, J. Am. Chem. Soc. 1994, 116, 5505.
13. Lading references for applications to the synthesis of natural products: a) D. C. Billington, P. L. Pauson, Organometallics 1982, 1, 5861; b) C. Exon, P. Magnus, J. Am. Chem. Soc. 1983, 105, 2477; c) N. E. Schore, E. G. Rowley, ibid. 1988, 110, 5224; d) S. Takano, K. Inomata, K. Ogasawara, J. Chem. Soc. Chem. Commun. 1992, 169; e) S. Takano, K. Inomata, K. Ogasawara, Chem. Lett. 1992, 443; f) S. Yoo, S.-H. Lee, N. Jeong, I. Cho, Tetrahedron Lett. 1993, 34, 3435; g) T. F. Jamison, S. Shambayati, W. E. Crowe, S. L. Schreiber, J. Am. Chem. Soc. 1994, 116, 5505.
14. Lading references for applications to the synthesis of natural products: a) D. C. Billington, P. L. Pauson, Organometallics 1982, 1, 5861; b) C. Exon, P. Magnus, J. Am. Chem. Soc. 1983, 105, 2477; c) N. E. Schore, E. G. Rowley, ibid. 1988, 110, 5224; d) S. Takano, K. Inomata, K. Ogasawara, J. Chem. Soc. Chem. Commun. 1992, 169; e) S. Takano, K. Inomata, K. Ogasawara, Chem. Lett. 1992, 443; f) S. Yoo, S.-H. Lee, N. Jeong, I. Cho, Tetrahedron Lett. 1993, 34, 3435; g) T. F. Jamison, S. Shambayati, W. E. Crowe, S. L. Schreiber, J. Am. Chem. Soc. 1994, 116, 5505.
15. Lading references for applications to the synthesis of natural products: a) D. C. Billington, P. L. Pauson, Organometallics 1982, 1, 5861; b) C. Exon, P. Magnus, J. Am. Chem. Soc. 1983, 105, 2477; c) N. E. Schore, E. G. Rowley, ibid. 1988, 110, 5224; d) S. Takano, K. Inomata, K. Ogasawara, J. Chem. Soc. Chem. Commun. 1992, 169; e) S. Takano, K. Inomata, K. Ogasawara, Chem. Lett. 1992, 443; f) S. Yoo, S.-H. Lee, N. Jeong, I. Cho, Tetrahedron Lett. 1993, 34, 3435; g) T. F. Jamison, S. Shambayati, W. E. Crowe, S. L. Schreiber, J. Am. Chem. Soc. 1994, 116, 5505.
16. Lading references for applications to the synthesis of natural products: a) D. C. Billington, P. L. Pauson, Organometallics 1982, 1, 5861; b) C. Exon, P. Magnus, J. Am. Chem. Soc. 1983, 105, 2477; c) N. E. Schore, E. G. Rowley, ibid. 1988, 110, 5224; d) S. Takano, K. Inomata, K. Ogasawara, J. Chem. Soc. Chem. Commun. 1992, 169; e) S. Takano, K. Inomata, K. Ogasawara, Chem. Lett. 1992, 443; f) S. Yoo, S.-H. Lee, N. Jeong, I. Cho, Tetrahedron Lett. 1993, 34, 3435; g) T. F. Jamison, S. Shambayati, W. E. Crowe, S. L. Schreiber, J. Am. Chem. Soc. 1994, 116, 5505.
17. For instance, see C. M. Lukehart, Fundamental Transition Metal Organometallic Chemistry, Brooks/Cole, Monterey, 1985.
18. There is an example in which THF, a "hard" ligand, is used as a promoter for ligand substitution reactions in the synthesis of [Cr(CO)3(arene)] complexes. C. A. L. Mahaffy, P. L. Pauson, Inorg. Synth. 1979, 19, 155.
19. Other promoters for the Pauson-Khand reaction have been reported. Amine oxides: a) S. Shambayati, W. E. Crowe, S. L. Schreiber, Tetrahedron Lett. 1990, 31, 5289; b) N. Jeong, Y. K. Chung, B. Y. Lee, S. H. Lee, S.-E. Yoo, Synlett 1991, 204; c) W. J. Kerr, G. G. Kirk, D. Middlemiss, ibid. 1995, 1085. Phosphine oxides: d) D. C. Billington, I. M. Helps, P. L. Pauson, W. Thomson, D. Willson, J. Organomet. Chem. 1988, 354, 233. Sulfoxides: e) Y. K. Chung, B. Y. Lee, N. Jeong, M. Hudecek, P. L. Pauson, Organometallics, 1993, 12, 220.
20. Other promoters for the Pauson-Khand reaction have been reported. Amine oxides: a) S. Shambayati, W. E. Crowe, S. L. Schreiber, Tetrahedron Lett. 1990, 31, 5289; b) N. Jeong, Y. K. Chung, B. Y. Lee, S. H. Lee, S.-E. Yoo, Synlett 1991, 204; c) W. J. Kerr, G. G. Kirk, D. Middlemiss, ibid. 1995, 1085. Phosphine oxides: d) D. C. Billington, I. M. Helps, P. L. Pauson, W. Thomson, D. Willson, J. Organomet. Chem. 1988, 354, 233. Sulfoxides: e) Y. K. Chung, B. Y. Lee, N. Jeong, M. Hudecek, P. L. Pauson, Organometallics, 1993, 12, 220.
21. Other promoters for the Pauson-Khand reaction have been reported. Amine oxides: a) S. Shambayati, W. E. Crowe, S. L. Schreiber, Tetrahedron Lett. 1990, 31, 5289; b) N. Jeong, Y. K. Chung, B. Y. Lee, S. H. Lee, S.-E. Yoo, Synlett 1991, 204; c) W. J. Kerr, G. G. Kirk, D. Middlemiss, ibid. 1995, 1085. Phosphine oxides: d) D. C. Billington, I. M. Helps, P. L. Pauson, W. Thomson, D. Willson, J. Organomet. Chem. 1988, 354, 233. Sulfoxides: e) Y. K. Chung, B. Y. Lee, N. Jeong, M. Hudecek, P. L. Pauson, Organometallics, 1993, 12, 220.
22. Other promoters for the Pauson-Khand reaction have been reported. Amine oxides: a) S. Shambayati, W. E. Crowe, S. L. Schreiber, Tetrahedron Lett. 1990, 31, 5289; b) N. Jeong, Y. K. Chung, B. Y. Lee, S. H. Lee, S.-E. Yoo, Synlett 1991, 204; c) W. J. Kerr, G. G. Kirk, D. Middlemiss, ibid. 1995, 1085. Phosphine oxides: d) D. C. Billington, I. M. Helps, P. L. Pauson, W. Thomson, D. Willson, J. Organomet. Chem. 1988, 354, 233. Sulfoxides: e) Y. K. Chung, B. Y. Lee, N. Jeong, M. Hudecek, P. L. Pauson, Organometallics, 1993, 12, 220.
23. Other promoters for the Pauson-Khand reaction have been reported. Amine oxides: a) S. Shambayati, W. E. Crowe, S. L. Schreiber, Tetrahedron Lett. 1990, 31, 5289; b) N. Jeong, Y. K. Chung, B. Y. Lee, S. H. Lee, S.-E. Yoo, Synlett 1991, 204; c) W. J. Kerr, G. G. Kirk, D. Middlemiss, ibid. 1995, 1085. Phosphine oxides: d) D. C. Billington, I. M. Helps, P. L. Pauson, W. Thomson, D. Willson, J. Organomet. Chem. 1988, 354, 233. Sulfoxides: e) Y. K. Chung, B. Y. Lee, N. Jeong, M. Hudecek, P. L. Pauson, Organometallics, 1993, 12, 220.
24. The rate enhancement in the Pauson - Khand reaction was observed with the substrates possessing tertiary amines or sulfides. M. E. Krafft, I. L. Scott, R. H. Romero, S. Feibelmann, C. E. Van Pelt, J. Am. Chem. Soc. 1993, 115, 7199.
25. For a report that the amine could stabilize the coordinatively unsaturated Co intermediate, see ref. [6b,c].
26. Recent reviews about reactions in a biphasic system: a) W. A. Herrmann, C. W. Kohlpaintner, Angew. Chem. 1993, 105, 1588; Angew. Chem. Int. Ed. Engl. 1993, 32, 1524; b) A. Lubineau, J. Augé, Y. Queneau, Synthesis 1994, 741.
27. Recent reviews about reactions in a biphasic system: a) W. A. Herrmann, C. W. Kohlpaintner, Angew. Chem. 1993, 105, 1588; Angew. Chem. Int. Ed. Engl. 1993, 32, 1524; b) A. Lubineau, J. Augé, Y. Queneau, Synthesis 1994, 741.
28. Recent reviews about reactions in a biphasic system: a) W. A. Herrmann, C. W. Kohlpaintner, Angew. Chem. 1993, 105, 1588; Angew. Chem. Int. Ed. Engl. 1993, 32, 1524; b) A. Lubineau, J. Augé, Y. Queneau, Synthesis 1994, 741.
29. Spectroscopically pure samples of cyclopentenones could not be obtained from the Pauson-Khand reaction under simple thermal conditions [1,2] in some cases without passing through silica gel pads.
30. See also E. Negishi in Comprehensive Organic Synthesis, Vol. 5 (Eds.: B. M. Trost, I. Fleming, L. A. Paquette), Pergamon, Oxford, 1991, p. 1163.
31. -. a) F. Francalanci, M. Foá, J. Organomet. Chem. 1982, 232, 59; b) P. Eilbracht, E. Balb, M. Acker, Tetrahedron Lett. 1984, 25, 1131; c) M. Miura, F. Akase, M. Nomura, J. Org. Chem. 1987, 52, 2623; d) C. Zucchi, G. Pályi, V. Galamb, E. Sámpár-Szerencsés, L. Markó, P. Li, H. Alper, Organometallics 1996, 15, 3222.
32. -. a) F. Francalanci, M. Foá, J. Organomet. Chem. 1982, 232, 59; b) P. Eilbracht, E. Balb, M. Acker, Tetrahedron Lett. 1984, 25, 1131; c) M. Miura, F. Akase, M. Nomura, J. Org. Chem. 1987, 52, 2623; d) C. Zucchi, G. Pályi, V. Galamb, E. Sámpár-Szerencsés, L. Markó, P. Li, H. Alper, Organometallics 1996, 15, 3222.
33. -. a) F. Francalanci, M. Foá, J. Organomet. Chem. 1982, 232, 59; b) P. Eilbracht, E. Balb, M. Acker, Tetrahedron Lett. 1984, 25, 1131; c) M. Miura, F. Akase, M. Nomura, J. Org. Chem. 1987, 52, 2623; d) C. Zucchi, G. Pályi, V. Galamb, E. Sámpár-Szerencsés, L. Markó, P. Li, H. Alper, Organometallics 1996, 15, 3222.
34. -. a) F. Francalanci, M. Foá, J. Organomet. Chem. 1982, 232, 59; b) P. Eilbracht, E. Balb, M. Acker, Tetrahedron Lett. 1984, 25, 1131; c) M. Miura, F. Akase, M. Nomura, J. Org. Chem. 1987, 52, 2623; d) C. Zucchi, G. Pályi, V. Galamb, E. Sámpár-Szerencsés, L. Markó, P. Li, H. Alper, Organometallics 1996, 15, 3222.