Non-sonogashira-type palladium-catalyzed coupling reactions of terminal alkynes assisted by silver(I) oxide or tetrabutylammonium fluoride

Organic Letters

Volumn 2, Issue 19, 2000, Pages 2935-2937

  Mori, Atsunori ^a   Kawashima, Jun ^a   Shimada, Tomohiro ^a   Suguro, Masahiro ^a   Hirabayashi, Kazunori ^a   Nishihara, Yasushi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

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Indexed keywords

EID: 0000073456     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0061586     Document Type: Article

References (27)

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4. (b) Nishihara, Y.; Ikegashira, K.; Hirabayashi, K.; Ando, J.; Mori, A.; Hiyama, T. J. Org. Chem. 2000, 65, 1780.
5. (c) Nishihara, Y.; Ando, J.; Kato, T.; Mori, A.; Hiyama, T. Macromolecules 2000, 33, 2779.
6. (a) Campbell, I. B. In Organocopper Reagents. A Practical Approach; Taylor, R. J. K., Ed.; Oxford University Press: Oxford, 1994; Chapter 10, pp 217-236.
7. (b) Sonogashira, K. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P. J., Eds; Wiley: Weinheim, 1997; Chapter 5, pp 203-229.
8. (a) Hirabayashi, K.; Kawashima, J.; Nishihara, Y.; Mori, A.; Hiyama, T. Org. Lett. 1999, 1, 299.
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10. (c) Hirabayashi, K.; Mori, A,; Kawashima, J.; Suguro M.; Nishihara, Y.; Hiyama, T. J. Org. Chem. In press.
11. See also: (a) Hirabayashi, K.; Nishihara, Y.; Mori, A.; Hiyama, T. Tetrahedron Lett. 1998, 39, 7893.
12. (b) Mateo, C.; Fernández-Rivas, C.; Echavarren, A. M.; Cárdenas, D. J. Organometallics 1997, 16, 1997.
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14. (a) Hatanaka, Y.; Matsui, K.; Hiyama, T. Tetrahedron Lett. 1989, 30, 2403.
15. (b) For a review: Hiyama, T. In Metal-Catalyzed Cross-Coupling Reactions; Diederich, F., Stang, P., Eds; Wiley: Weinheim, 1997; Chapter 10, pp 421-453.
16. 2O (1 mol amount) afforded the coupling product in 98% yield.
17. 2CO3 was recently reported independently: Koseki, Y.; Omino, K.; Anzai, S.; Nagasaka, T. Tetrahedron Lett. 2000, 41, 2377.
18. See Supporting Information.
19. Attempted reaction with a triflate under similar conditions gave unidentified products.
20. For a review on the use of fluoride ion, see: Clark, J. H. Chem. Rev. 1980, 429.
21. (a) Pilcher, A. S.; DeShong, P J. Org. Chem. 1996, 61, 6901.
22. (b) Hosomi, A.; Shirahata, A.; Sakurai, H. Tetrahedron Lett. 1978, 3043.
23. Although several coupling reactions of terminal alkynes have been shown to proceed without Cu(I), the use of highly reactive organic electrophiles and/or excess amounts of amine as a (co)solvent are necessary. For example: (a) Austin W. B.; Bilow, N.; Kelleghan, W. J.; Lau, K. S. Y. J. Org. Chem. 1981, 46, 2280.
24. (b) Alami, M.; Ferri, F.; Linstrumelle, G. Tetrahedron Lett. 1993, 34, 6403.
25. (c) Schaus, J.; Panek, J. S. Org. Lett. 2000, 2, 469. See also the use of AgI instead of CuI:
26. (d) Bertus, P.; Pale P. Tetrahedron Lett. 1996, 37, 2019.
27. 2O (90%: 60°C, 8 h), TBAF (82%: 60 °C, 3 h), and typical Sonogashira conditions (see ref 3b) (91%: rt, 1 h).