First Evidence for the Use of Organosilver Compounds in Pd-Catalyzed Coupling Reactions; A Mechanistic Rationale for the Pd/ Ag-Catalyzed Enyne Synthesis?

Organic Letters

Volumn 3, Issue 11, 2001, Pages 1661-1664

  Dillinger, Sandra ^a   Bertus, Philippe ^a,b   Pale, Patrick ^a  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b UNIVERSITÉ DE REIMS CHAMPAGNE ARDENNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000860028     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol015830b     Document Type: Article

References (41)

1. Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron Lett. 1992, 33, 5355-5358. Dalla, V.; Pale, P. Tetrahedron Lett. 1994, 35, 3525-3528.
2. Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron Lett. 1992, 33, 5355- 5358. Dalla, V.; Pale, P. Tetrahedron Lett. 1994, 35, 3525-3528.
3. Grandjean, D.; Pale, P.; Chuche, J. Tetrahedron 1993, 49, 5225-5236.
4. (a) Ishida, N.; Miyazaki, K.; Kumagai, K. M.; Rikimura, M. J. Antibiot. 1965, 18, 68-76.
5. (b) Edo, K.; Mizugaki, M.; Koide, Y.; Seto, H.; Furihata, K.; Otake, N.; Ishida, N. Tetrahedron Lett. 1985, 26, 331-334.
6. N1999A2: (a) Ishii, M.; Ando, T.; Kajiura, T.; Kameyama, T.; Nihey, Y. Jpn. Kokai Tokkyo Koho JP 07291955; Chem. Abstr. 1996, 124, 115564h.
7. (b) Ando, T.; Ishii, M.; Kajiura, T.; Kameyama, T.; Miwa, K.; Sugiura, Y. Tetrahedron Lett. 1998, 39, 6495-6498. Kedarcidine:
8. (c) Hofstead, S. J.; Matson, J. A.; Malacko, A. R.; Marquard, H. J. Antibiot. 1992, 45, 1250-1254.
9. (d) Leet, J. E.; Schroeder, D. R.; Hofstead, S. J.; Golik, J.; Colson, K. L.; Huang, S.; Klohr, S. E.; Doyle, T. W.; Matson, J. A. J. Am. Chem. Soc. 1992, 114, 7946-7948. C-1027:
10. (e) Zhen, Y.-S.; Ming, X.-Y.; Yu, B.; Otani, T.; Saito, H.; Yamada, Y. J. Antibiot. 1989, 42, 1294-1298.
11. (f) Yoshida, K.-I.; Minami, Y.; Azuma, R.; Saeki, M.; Otani, T. Tetrahedron Lett. 1993, 34, 2637-2640. Maduropeptine:
12. (g) Hanada, M.; Ohkuma, H.; Yonemoto, T.; Tomita, K.; Ohbayashi, M.; Kamei, H.; Miyaki, T.; Konishi, M. M.; Kawaguchi, H., Forenza, S. J. Antibiot. 1991, 44, 403-414.
13. (h) Schroeder, D. R.; Colson, K. L.; Klohr, S. E.; Zein, N.; Langley, D. R.; Lee, M.; Matson, J. A.; Doyle, T. W. J. Am. Chem. Soc. 1994, 116, 9351-9352.
14. For recent reviews dealing with the synthesis of such compounds, see: (a) Nicolaou, K. C.; Smith, A. L. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds; VCH: Weinheim, 1995; pp 203-283.
15. (b) Lhermitte, H.; Grierson, D. S. Contemp. Org. Synth. 1996, 41-63 and 93-124.
16. (c) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453-6518.
17. (a) Bertus, P.; Pale, P. Tetrahedron Lett. 1996, 37, 2019-2022.
18. (b) Bertus, P.; Pale, P. Tetrahedron Lett. 1997, 38, 8193-8196.
19. Bertus, P.; Pale, P. J. Organomet. Chem. 1998, 567, 173-180.
20. Sonogashira, K. In Comprehensive Organic Chemistry; Fleming, I., Trost, B. M., Eds; Pergamon: Oxford, 1991; Vol. 3, pp 521-549.
21. The occurrence of copper acetylides has been suggested as in situ formed intermediates in Sonogashira-Linstrumelle reactions. We thus looked for less nucleophilic intermediates in order to avoid side reactions observed with sensitive triflates and acetylenes; see refs 6 and 17.
22. A simplified version of the Pd-catalytic cycle has been drawn for convenience. Cationic palladium species having the triflate as counterion and/or anionic pentacoordinated palladium complexes are probably involved in this cycle. For more details, see: Amatore, C.; Jutand, A.; Suarez, A. J. Am. Chem. Soc. 1993, 115, 9631-9641. Jutand, A.; Mosleh, A. Organometallics 1995, 14, 1810-1817.
23. A simplified version of the Pd-catalytic cycle has been drawn for convenience. Cationic palladium species having the triflate as counterion and/or anionic pentacoordinated palladium complexes are probably involved in this cycle. For more details, see: Amatore, C.; Jutand, A.; Suarez, A. J. Am. Chem. Soc. 1993, 115, 9631-9641. Jutand, A.; Mosleh, A. Organometallics 1995, 14, 1810-1817.
24. To our knowledge, no details are so far available for the mechanism of the copper catalysis in these reactions.
25. Noltes, J. G.; Van Koten, G. In Comprehensive Organometallic Chemistry I; Wilkinson, G., Abel, E. W., Stone, F. G. A., Eds; Pergamon: Oxford, 1982; Vol. 2, p 709. Van Koten, G.; James, S. L. Jastrzebski, J. T. B. H. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds; Pergamon: Oxford, 1995; Vol. 3, p 57.
26. Noltes, J. G.; Van Koten, G. In Comprehensive Organometallic Chemistry I; Wilkinson, G., Abel, E. W., Stone, F. G. A., Eds; Pergamon: Oxford, 1982; Vol. 2, p 709. Van Koten, G.; James, S. L. Jastrzebski, J. T. B. H. In Comprehensive Organometallic Chemistry II; Abel, E. W., Stone, F. G. A., Wilkinson, G., Eds; Pergamon: Oxford, 1995; Vol. 3, p 57.
27. (a) Pale, P.; Chuche, J. Tetrahedron Lett. 1987, 28, 6447-6448.
28. (b) Dalla, V.; Pale, P. Tetrahedron Lett. 1994, 35, 3525-3528.
29. (c) Dalla, V.; Pale, P. New J. Chem. 1999, 23, 803-805.
30. (d) Pale, P.; Chuche, J. Eur. J. Org. Chem. 2000, 1019-1025.
31. Lewandos, G. S.; Maki, J. W.; Ginnebaugh, J. P. Organometallics 1982, 1, 1700. In situ formed silver acetylides can also be trapped by halogen; see: Hofmeister, H.; Annen, K.; Laurent, H.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1984, 23, 727-728.
32. Lewandos, G. S.; Maki, J. W.; Ginnebaugh, J. P. Organometallics 1982, 1, 1700. In situ formed silver acetylides can also be trapped by halogen; see: Hofmeister, H.; Annen, K.; Laurent, H.; Wiechert, R. Angew. Chem., Int. Ed. Engl. 1984, 23, 727-728.
33. Travkin, I. J. Gen. Chem. USSR (Engl. Transl.) 1976, 46, 1081. Davis, R. B.; Scheiber, D. H. J. Am. Chem. Soc. 1956, 78, 1675-1678.
34. Travkin, I. J. Gen. Chem. USSR (Engl. Transl.) 1976, 46, 1081. Davis, R. B.; Scheiber, D. H. J. Am. Chem. Soc. 1956, 78, 1675-1678.
35. 9. The silver acetylide-silver nitrate has already been isolated; see: Chevastelon, R. C. R. Acad. Sci. 1897, 124, 1364.
36. Bertus, P. thèse de doctorat. Université de Reims-Champagne-Ardenne, Reims, 1997. General Procedure. Silver nitrate (2.1 equiv) was suspended in a mixture of water (3 M) and methanol (5 M). To this suspension kept in the dark was dropwise added an aqueous ammoniac solution until the solution was homogeneous, and then the alkyne (1 eq) was added. A white solid rapidly formed, which was filtered off. The solid was then washed with water and dried under vacuum. The solid so obtained (85-95% yield) must be preserved from light but is not air sensitive; it is readily soluble in organic solvents.
37. 9Ag: C, 38.1; H, 4.7. Found: C, 35.5; H, 4.3; N, 0.5.
38. 4, filtered, and concentrated under reduced pressure. The crude enyne was then purified by chromatography.
39. Amatore, C.; Jutand, A.; Amine M'Barki, M. Organometallics 1992, 11, 3009-3013.
40. Stang, P.; Kowalski, M. H.; Schiavelli, M. D.; Longford, D. J. Am. Chem. Soc. 1989, 111, 3347-3356.
41. Bertus, P.; Pale, P. Unpublished results, see also refs 6, 7, and 17.