Palladium-catalyzed three-component coupling reaction of aryl halides, norbornadiene and alkynols. Convenient synthesis for their ternary coupling products

Chemistry Letters

Volumn , Issue 11, 1999, Pages 1253-1254

  Choi, Cheol Kyu ^a   Tomita, Ikuyoshi ^a   Endo, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0033474575     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.1999.1253     Document Type: Article

References (28)

1. M. Catellani and G. P. Chiusoli, Tetrahedron Lett., 23, 4517 (1982).
2. M. Catellani, G. P. Chiusoli, and S. Concari, Tetrahedron, 45, 5263 (1989).
3. S. Torii, H. Okumoto, H. Ozaki, S. Nakayasu, and T. Kotani, Tetrahedron Lett., 31, 5319 (1990).
4. N. Chatani, N. Amishiro, and S. Murai, J. Am. Chem. Soc., 113, 7778 (1991).
5. F. Ozawa, Y. Kobatake, A. Kubo, and T. Hayashi, J. Chem. Soc., Chem. Commun., 1994, 1323.
6. N. Chatani, N. Amishiro, T. Morii, T. Yamasita, and S. Murai, J. Org. Chem., 60, 1834 (1995).
7. a) N. Miyaki, I. Tomita, and T. Endo, Macromolecules, 29, 6685 (1996).
8. b) N. Miyaki, I. Tomita, and T. Endo, J. Polym. Sci.: Part A: Polym. Chem., 35, 1211 (1997).
9. c) N. Miyaki, I. Tomita, and T. Endo, J. Polym. Sci.: Part A: Polym. Chem., 35, 2097 (1997).
10. d) N. Miyaki, I. Tomita, and T. Endo, Macromolecules, 30, 4504 (1997).
11. e) N. Miyaki, I. Tomita, and T. Endo, Chem. Lett., 1997, 685.
12. f) N. Miyaki, I. Tomita, T. Endo, Polym. Bull. 39, 677 (1997).
13. M. Kosugi, H. Tamura, H. Sano, and T. Migita, Chem. Lett., 1987, 193.
14. M. Kosugi, H. Tamura, H. Sano, and T. Migita, Tetrahedron, 45, 961 (1989).
15. M. Kosugi, T. Kimura, H. Oda, and T. Migita, Bull. Chem. Soc. Jpn., 66, 3522 (1993).
16. H. Oda, K. Ito, M. Kosugi, and T. Migita, Chem. Lett., 1994, 1443.
17. H. Oda, K. Hamataka, K. Fugami, M. Kosugi, and T. Migita, Synlett 1995, 1225.
18. R. C. Larock and S. Babu, Tetrahedron, 43, 2013 (1987).
19. S. Torii, H. Okumoto, H. Ozaki, S. Nakayasu, T. Tadokoro, and T. Kotani, Tetrahedron Lett., 33, 3499 (1992).
20. S. Torii, H. Okumoto, H. T. Kotani, S. Nakayasu, and H. Ozaki, Tetrahedron Lett., 33, 3503 (1992).
21. In fact, when the reaction of bromobenzene and 4-methoxyphenylacetylene was carried out under the conditions employed for the present study, the binary coupling product (a tolane derivative) was obtained in 32% yield besides the ternary coupling product (64%).
22. Both bis(tributylstannyl)acetylene and 2,5-dimethyl-3-hexyn-2,5-diol are available from Aldrich Co., Inc, whose prices are $8,500/mole and $31/mole, respectively derived from the largest sized bottles listed in the 1996-97 catalog.
23. a) S. J. De Mora, Tributyltin: Case Study of an Environmental Contaminant, Cambridge University Cambridge, 1966.
24. b) I. J. Boyer, Toxicology, 55, 253 (1989).
25. a) C. Huynh and G. Linstrumelle, Tetrahedron, 44, 6337 (1988).
26. b) V. A. Solomin and W. Heitz, Macromol. Chem. Phys. 195, 303 (1994).
27. 20O: C, 87.96; H, 6.71; O, 5.33%.
28. 2Na, from which the ternary coupling product was obtained in 94%, 91%, 62%, 14%, and 5% yields, respectively. Thus, NaOH was used for the present study.