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

Abstract

A number of alkynes 5, allene 11 and alkene 13 smoothly underwent hydrostannation with tributyltin hydride 1, prepared in situ from tributylchlorostannane 6 and triethylsilane 7 in the presence of catalytic amounts of Lewis acids.

References

1. A. E. Finholt, 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; Y. Ichinose, H. Oda, K. Oshima and K. Utimoto, Bull. Chem. Soc. Jpn., 1987, 60, 3468; K. Kikuhawa, F. Umekawa, G. Wada and T. Matsuda, Chem. Lett., 1988, 881; H. Miyake and K. Yamamura, Chem. Lett., 1989, 981.
4. H. G. Kuivila, W. Rahman and R. H. Fish, J. Am. Chem. Soc., 1965, 87, 2835; M. Koreeda and Y. Tanaka, Tetrahedron Lett., 1987, 28, 143; Y. Ichinose, K. Oshima and K. Utimoto, Bull. Chem. Soc. Jpn., 1988, 61, 2693; T. N. Mitchell and U. Schneider, J. Organomet. Chem., 1991, 405, 195; K. Koerber, J. Gore and J.-M. Vatele, Tetrahedron Lett., 1991, 32, 1187.
5. (a) M. Pereyre, J.-P. Quintard and A. Rahm, Tin in Organic Synthesis, Butterworths, London, 1987; (b) A. J. Leusink, H. A. Budding and W. Drenth, J. Organomet. Chem., 1967, 9, 285; 1967, 9, 295; (c) Y. Yamamoto and N. Asao, Chen, Rev., 1993, 93, 2207; (d) J. K. Stille, Angew. Chem., Int. Ed. Engl., 1986, 25, 508; (e) R. F. Heck, Palladium Reagents in Organic Synthesis, Academic Press, New York, 1985.
6. N. Asao, J.-X. Liu, T. Sudoh and Y. Yamamoto, J. Org. Chem., 1996, 61, 4568; N. Asao, J.-X. Liu, T. Sudoh and Y. Yamamoto, J. Chem. Soc., Chem. Commun., 1995, 2405.
7. V. Gevorgyan, J.-X. Liu and Y. Yamamoto, J. Org. Chem., 1997, 62, 2963.
8. 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; 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).
9. The reduction of various organic halides with 1 prepared in situ from tributyltin chloride and LiAlH₄ or NaBH₄ has been reported: E. J. Corey and J. W. Suggs, J. Org. Chem., 1975, 40, 2554; 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.
10. K. Hayashi, J. Iyoda and I. Shiihara, J. Organomet. Chem., 1967, 10, 81.
11. Since ZrCl₄ was reported to be the best Lewis acid catalyst for trans-hydrostannation of alkynes with Bu₃SnH⁶ it was chosen for our initial experiments for the in situ hydrostannation of alkynes.
12. N. Asao, T. Sudoh and Y. Yamamoto, J. Org. Chem., 1996, 61, 7654.