Lewis acid catalyzed allylstannylation of unactivated alkynes

Tetrahedron

Volumn 55, Issue 12, 1999, Pages 3779-3790

  Matsukawa, Yasuhisa ^a   Asao, Naoki ^a   Kitahara, Haruo ^b   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b HIROSAKI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

2,4 CYCOHEXENYL 1 TRIBUTYLSTANNYL 1,4 PENTADIENE; 2,4 METHOXYPHENYL 1 TRIBUTYLSTANNYL 1,4 PENTADIENE; 2,4 TOLYL 1 TRIBUTYLSTANNYL 1,4 PENTADIENE; ACETYLENE; ALKYNE; ALLYL COMPOUND; ALUMINUM CHLORIDE; AROMATIC COMPOUND; UNCLASSIFIED DRUG; ZIRCONIUM DERIVATIVE;

ACIDITY; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL REACTION KINETICS; CHEMICAL STRUCTURE; COMPLEX FORMATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033583167     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)01183-1     Document Type: Article

References (30)

1. Ziegler, K.; Bähr, K. Chem. Ber. 1928, 67, 253.
2. For reviews, see: (a) Normant, J. F.; Alexakis, A. Synthesis 1981, 841 (organo-Li, Mg, Zn, B, Al and Cu compounds).
3. (b) Negishi, E. Pure & Appl. Chem. 1981, 53, 2333 (organo-Al / Ti and Al / Zr systems).
4. (c) Oppolzer, W.; Angew. Chem. Int., Ed. Engl. 1989, 28, 38 (stoichiometric organo-Li, Mg, Zn and catalytic Ni, Pd, Pt compounds).
5. (d) Knochel, P. In Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds.; Pergamon Press: Oxford, U.K., 1991; Vol. 4, p 865.
6. (e) Yamamoto, Y.; Asao, N. Chem. Rev. 1993, 93, 2207 (organo-Li, Mg, Zn, B, and Al compounds).
7. (f) Knochel, P. In Comprehensive Organometallic Chemistry II, Abel, E. W.; Stone, F. G. A.; Wilkinson, G., Eds.; Pergamon Press: Oxford, U.K., 1995; Vol. 11, p 159 (organo-Li, Mg, Zn, B, Al, Cu, Hg/Pd,Ni, and Mn compounds).
8. (a) Araki, S.; Imai, A.; Shimizu, K.; Yamada, M; Mori, A.; Butsugan, Y. J. Org. Chem. 1995, 60, 1841 (allylindiums).
9. (b) Okada, K.; Oshima, K.; Utimoto, K. J. Am. Chem. Soc. 1996, 118, 6076; Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Tetrahedron 1997, 53, 5061 (allyl-Mg/Mn).
10. (b) Okada, K.; Oshima, K.; Utimoto, K. J. Am. Chem. Soc. 1996, 118, 6076; Tang, J.; Okada, K.; Shinokubo, H.; Oshima, K. Tetrahedron 1997, 53, 5061 (allyl-Mg/Mn).
11. (a) Molander, G. A. J. Org. Chem. 1983, 48, 5409 (allyl-Zn).
12. (b) Negishi, E.; Miller, J. A. J. Am. Chem Soc. 1983, 105, 6761 (allyl-Zn).
13. (c) Miller, J. A.; Negishi, E. Tetrahedron Lett. 1984, 25, 5863 (allyl-Al).
14. (d) Eishi, J. J.; Boleslawski, M. P. J. Organomet. Chem. 1987, 334, Cl (allyl-Ti).
15. (e) Takahashi, T.; Kotora, M.; Kasai, K.; Suzuki, N. Tetrahedron Lett. 1994, 35, 5685 (allyl-Zr).
16. (f) Yeon, S. H.; Han, J. S.; Hong, E.; Do, Y.; Jung, I. N. J. Organomet. Chem. 1995, 499, 159 (allyl-Si).
17. (g) Takai, K.; Yamada, M.; Odaka, H.; Utimoto, K.; Fujii, T.; Furukawa, I. Chem. Lett. 1995, 315 (allyl-Ta).
18. (h) Chalani, N.; Amishiro, N.; Morii, T. ; Yamashita, T.; Murai, S. J. Org. Chem. 1995, 60, 1834 (allyl-Zn).
19. (i) Singleton, D. A.; Waller, S. C.; Zang, Z.; F Rantz, D. E.; Leung, S. -W. J. Am. Chem. Soc. 1996, 118 9986 (allyl-B).
20. (j) Yamaguchi, M.; Sotoyama, T; Hirama, M. J. Chem. Soc., Chem. Commun. 1997, 743 (allyl-Ga).
21. (k) Fujiwara.; N, Yamamoto, Y. J. Org. Chem. 1997, 62, 2318 (allyl-In).
22. (l) Ranu, B.; Majee, A.;J. Chem. Soc., Chem. Commun. 1997, 1225 (allyl-In).
23. (a) Asao, N.; Yoshikawa, E. Yamamoto, Y. J. Org. Chem. 1996, 61, 4874.
24. (b) Yoshikawa, E; Gevorgyan, V.; Asao, N.; Yamamoto, Y. J. Am. Chem, Soc, 1997, 119, 6781.
25. Asao, N.; Matsukawa, Y.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1513.
26. (a) Asao, N; Liu, J.-X.; Sudoh, T.; Yamamoto, Y. J. Chem. Soc., Chem. Commun. 1996, 1513.
27. (b) Asao, N; Liu, J.-X.; Sudoh, T.; Yamamoto, Y. J. Org. Chem. 1996, 61, 4568.
28. 3, did not catalyze the addition reaction of allyltributylstannane to 1a.
29. Asao, N.; Sudo, T.; Yamamoto, Y. J. Org. Chem. 1996, 61, 7654.
30. Kadota, I.; Ohno, A.; Matsukawa, Y.; Yamamoto, Y. Tetrahedron Lett., 1998, 39, 6373.