A facile regio- and stereocontrolled synthesis of (Z )-1-en-3-yn-2-ylstannanes via alkynyliodonium tosylates coupling with gem-stannyl zirconocene alkenes

Abstract

Acetylenic stannanes react with Cp₂Zr(H)Cl (Cp = η⁵-C₅H₅) giving organozirconium(IV) complexes, which are trapped with alkynyliodonium tosylates in the presence of Pd(PPh₃)₄ to afford (Z )-1-en-3-yn-2-ylstannanes.

References

1. P. J. Stang and T. Kitamura, J. Am. Chem. Soc., 1987, 109, 7561.
2. M. M. Salter, V. Gevorgyan, S. Saito and Y. Yamamoto, Chem. Commun., 1996, 17.
3. P. A. Magriotis and K. D. Kim, J. Am. Chem. Soc., 1993, 115, 2972.
4. E. J. Corey and A. Tramontano, J. Am. Chem. Soc., 1984, 106, 462.
5. N. Miyaura, K. Yamada, H. Suginome and A. Suzuki, J. Am. Chem. Soc., 1985, 107, 972.
6. A. Alexakis, G. Cahiez and J. F. Normant, Synthesis, 1979, 826.
7. M. Abarbri, J. L. Parrain, J. C. Cintrat and A. Duchêne, Synthesis, 1996, 82.
8. M. Kobayashi, L. F. Valente and E. Negishi, synthesis, 1980, 1034.
9. H. P. Dang and G. Linstrumelle, Tetrahedron Lett., 1978, 191.
10. R. Hara, Y. Liu, W. H. Sun and T. Takahashi, Tetrahedron Lett., 1997, 38, 4103.
11. P. J. Stang, B. W. Surber, Z. C. Chen, K. A. Roberts and A. G. Anderson, J. Am. Chem. Soc., 1987, 109, 228.
12. M. W. Logue and K. Teng, J. Org. Chem., 1982, 47, 2549.
13. S. L. Buchwald, S. J. LaMaire, R. B. Nielsen, B. T. Watson and S. N. King, Tetrahedron Lett., 1987, 28, 3895.
14. B. T. Grobel and D. Seebach, Chem. Ber., 1977, 110, 867.
15. A. Pelter, K. Smith, D. E. Parry and K. D. Jones, Aust. J. Chem., 1992, 45, 57.
16. R. A. Aithen, C. Boeters and J. J. Morrison, J. Chem. Soc., Perkin Trans. 1, 1994, 2473.
17. F. M. Beringer, M. Drexler, E. M. Gimdler and C. C. Lumpkin, J. Am. Chem. Soc., 1953, 75, 2705.
18. F. Mareuzzi, U. Azzena and G. Melloni, J. Chem. Soc., Perkin Trans. 1, 1993, 2957.