Hydrostannation of C-C multiple bonds with Bu3SnH prepared in situ from Bu3SnCl and Et3SiH in the presence of Lewis acid catalysts

Chemical Communications

Volumn , Issue 1, 1998, Pages 37-38

  Gevorgyan, Vladimir ^a   Liu, Jian Xiu ^a   Yamamoto, Yoshinori ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003155182     PISSN: 13597345     EISSN: None     Source Type: Journal    
DOI: 10.1039/a706187k     Document Type: Article

References (27)

1. A. E. Einholt, A. C. Bond, K. E. Wilzbach and H. I. Schlesinger, J. Am. Chem. Soc., 1947, 69, 2693.
2. For a leading review, see W. P. Neumann, Synthesis, 1987, 665.
3. H. X. Zhang, F. Guibé and G. Balavoine, J. Org. Chem., 1990, 55, 1857;
4. Y. Ichinose, H. Oda, K. Oshima and K. Utimoto, Bull. Chem. Soc. Jpn., 1987, 60, 3468;
5. K. Kikuhawa, F. Umekawa, G. Wada and T. Matsuda, Chem. Lett., 1988, 881;
6. H. Miyake and K. Yamamura, Chem. Lett., 1989, 981.
7. H. G. Kuivila, W. Rahman and R. H. Fish, J. Am. Chem. Soc., 1965, 87, 2835;
8. M. Koreeda and Y. Tanaka, Tetrahedron Lett., 1987, 28, 143;
9. Y. Ichinose, K. Oshima and K. Utimoto, Bull. Chem. Soc. Jpn., 1988, 61, 2693;
10. T. N. Mitchell and U. Schneider, J. Organomet. Chem., 1991, 405, 195;
11. K. Koerber, J. Gore and J.-M. Vatele, Tetrahedron Lett., 1991, 32, 1187.
12. (a) M. Pereyre, J.-P. Quintard and A. Rahm, Tin in Organic Synthesis, Butterworths, London, 1987;
13. (b) A. J. Leusink, H. A. Budding and W. Drenth, J. Organomet. Chem., 1967, 9, 285;
14. A. J. Leusink, H. A. Budding and W. Drenth, J. Organomet. Chem., 1967, 9, 295;
15. (c) Y. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207;
16. (d) J. K. Stille, Angew. Chem., Int. Ed. Engl., 1986, 25, 508;
17. (e) R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, New York, 1985.
18. N. Asao, J.-X. Liu, T. Sudoh and Y. Yamamoto, J. Org. Chem., 1996, 61, 4568;
19. N. Asao, J.-X. Liu, T. Sudoh and Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1995, 2405.
20. V. Gevorgyan, J.-X. Liu and Y. Yamamoto, J. Org. Chem., 1997, 62, 2963.
21. G. Bähr and S. Pawlenko, in Methoden der Organischen Chemie, ed. E. Müller and O. Bayer, Thieme Verlag, Stuttgart, 1978, vol. 13/6, p. 181;
22. A. G. Davies and P. J. Smith, in Comprehensive Organometallic Chemistry, ed. G. Wilkinson, Pergamon Press, Oxford, 1982, vol. 2, Tin, see also refs. 2, 5(a).
23. 4 has been reported: E. J. Corey and J. W. Suggs, J. Org. Chem., 1975, 40, 2554;
24. H. G. Kuivila and L. W. Menapace, J. Org. Chem., 1963, 28, 2165. However, due to the presence of reactive metal hydrides in the reaction mixture, this method could not be applied to the Lewis acid-catalyzed hydrostannation reaction.
25. K. Hayashi, J. Iyoda and I. Shiihara, J. Organomet. Chem., 1967, 10, 81.
26. 6 it was chosen for our initial experiments for the in situ hydrostannation of alkynes.
27. N. Asao, T. Sudoh and Y. Yamamoto, J. Org. Chem., 1996, 61, 7654.