Reaction of 1-iodoalkynes with allylzirconiums: Generation of alkylidene carbenoid via allylzirconation

Tetrahedron Letters

Volumn 40, Issue 14, 1999, Pages 2793-2796

  Yamanoi, Shigeo ^a   Matsumoto, Takashi ^a   Suzuki, Keisuke ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE DERIVATIVE; ZIRCONIUM DERIVATIVE;

ARTICLE; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; REACTION ANALYSIS; REACTION TIME; STOICHIOMETRY;

EID: 0033515775     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00296-8     Document Type: Article

References (31)

1. For reviews, see: (a) Braun, M. Angew. Chem., Int, Ed. Engl. 1998, 37, 430.
2. (b) Kirmse, W. Angew. Chem., Int, Ed. Engl. 1997, 36, 1164.
3. (c) Stang, P. J. Acc. Chem. Res. 1982, 15, 348.
4. (a) Yamanoi, S.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1998, 39, 9727.
5. (b) Yamanoi, S.; Imai, T.; Matsumoto, T.; Suzuki, K. Tetrahedron Lett. 1997, 38, 3031. (correction) ibid. 1997, 38, 5573.
6. (a) Chino, M.; Liang, G. H.; Matsumoto, T.; Suzuki, K. Chem. Lett. 1996, 231.
7. (b) Suzuki, K.; Hasegawa, T.; Imai, T.; Maeta, H.; Ohba, S. Tetrahedron 1995, 51, 4482.
8. (c) Chino, M.; Matsumoto, T.; Suzuki, K. Synlett 1994, 359.
9. (d) Maeta, H.; Hasegawa, T.; Suzuki, K. Synlett 1993, 341.
10. For allylmetallation of alkynes, see: (a) Yoshikawa, E.; Gevorgyan, V.; Asao, N.; Yamamoto, Y. J. Am. Chem. Soc. 1997, 119, 6781.
11. (b) Asao, N.; Matsukawa, Y.; Yamamoto, Y. Chem. Commun. 1996, 1513.
12. (c) Okada, K.; Oshima, K.; Utimoto, K. J. Am. Chem. Soc. 1996, 118, 6076.
13. (d) Suzuki, N.; Kondakov, D. Y.; Kageyama, M.; Kotora, M.; Hara, R.; Takahashi, T. Tetrahedron 1995, 51, 4519.
14. (e) Araki, S.; Imai, A.; Shimizu, K.; Butsugan, Y. Tetrahedron Lett. 1992, 33, 2581.
15. (f) Negishi, E.; Takahashi, T. Synthesis 1988, 1.
16. (g) Mikhailov, B. M. Pure Appl. Chem. 1974, 39, 505. See also, Nishimae, S.; Inoue, R.; Shinokubo, H.; Oshima, K. Chem. Lett. 1998, 785.
17. 3Al (2:1 ), Al = 6 wt% in toluene, mw = 1200, used for this reaction was kindly donated from Tosoh Akzo Co.
18. For nucleophilic substitution of alkylidene carbenoids, see: (a) Kasai, K.; Liu, Y.; Hara, R.; Takahashi, T. Chem. Commun. 1998, 1989.
19. (b) Kasatkin, A.; Whitby, R. J. Tetrahedron Lett. 1997, 38, 4857.
20. (c) Kocienski, P.; Barber, C. Pure Appl. Chem. 1990, 62, 1933.
21. (d) Negishi, E.; Akiyoshi, K.; O'Conner, B.; Takagi, K.; Wu, G. J. J. Am. Chem. Soc. 1989, 111, 3089.
22. (e) Miller, J. A. J. Org. Chem. 1989, 54, 998.
23. (f) Harada, T.; Hara, D.; Hattori, K.; Oku, A. Tetrahedron Lett. 1988, 29, 3821.
24. (g) Zweifel, G.; Arzoumanian, H. J. Am. Chem. Soc. 1967, 89, 5086.
25. (a) Schwartz, J.; Labinger, J. A. Angew. Chem., Int. Ed. Engl. 1976, 15, 333.
26. (b) Buchwald, S. L.; LaMaire, S. J.; Nielsen, R. B.; Watson, B. T.; King, S. M. Org. Synth. 1992, 71, 77.
27. 13C NMR, IR, and high-resolution MS and/or combustion analysis.
28. 13C). (Formula presented)
29. 13C), has the labelled carbon at the inner position (cf. 2a*, 2h*). (Formula presented)
30. All attempts to quench the reaction in various periods failed to give the hydrolysate of the assumed intermediates F or H.
31. Copper-catalyzed coupling of alkenylzirconocenes with alkynyl halides has been reported, see: Hara, R.; Liu, Y.; Sun, W.-H.; Takahashi, T. Tetrahedron Lett. 1997, 38, 4103. see also ref. 6a.