Copper(i) salt promoted homo-coupling reaction of organosilanes

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Kazutaka Ikegashira, Yasushi Nishihara, Kazunori Hirabayashi, Atsunori Mori and Tamejiro Hiyama


Abstract

Alkenylfluorosilanes, phenylfluorosilanes or alkynylsilanes smoothly dimerize in the presence of a copper(I) salt in a polar solvent such as N,N-dimethylformamide (DMF) or dimethyl sulfoxide (DMSO) to give the 1,3-conjugated dienes, biphenyl or 1,3-conjugated diynes, respectively.


References

  1. T. Hiyama and Y. Hatanaka, Pure Appl. Chem., 1994, 66, 1471 CrossRef CAS; H. Matsuhashi, M. Kuroboshi, Y. Hatanaka and T. Hiyama, Tetrahedron Lett., 1994, 35, 6507 CrossRef CAS; H. Matsuhashi, Y. Hatanaka, M. Kuroboshi and T. Hiyama, Heterocycles, 1996, 42, 375 CrossRef CAS; H. Matsuhashi, S. Asai, K. Hirabayashi, Y. Hatanaka, A. Mori and T. Hiyama, Bull. Chem. Soc. Jpn., 1997, 70, 445; C. Chuit, R. J. P. Corriu, C. Reye and J. C. Young, Chem. Rev., 1993, 93, 1371 CrossRef CAS; K. A. Horn, Chem. Rev., 1995, 95, 1371.
  2. H. Matsuhashi, Y. Hatanaka, M. Kuroboshi and T. Hiyama, Tetrahedron Lett., 1995, 36, 1539 CrossRef CAS; E. Hagiwara, K.-i. Gouda, Y. Hatanaka and T. Hiyama, Tetrahedron Lett., 1996, 38, 439 CrossRef CAS.
  3. J.-i. Yoshida, K. Tamao, T. Kakui and M. Kumada, Tetrahedron Lett., 1979, 13, 1141 CrossRef.
  4. For reviews on transmetalation in organocopper chemistry, see P. Wipf, Synthesis, 1993, 537 Search PubMed and references cited therein.
  5. It has been reported that the allylation of aldehydes with allyltrichlorosilanes could be promoted by DMF or HMPA: S. Kobayashi and K. Nishio, Tetrahedron Lett., 1993, 34, 3453 Search PubMed; J. Org. Chem., 1994, 59, 6620 CrossRef CAS; S. E. Denmark, D. M. Coe, N. E. Pratt and B. D. Griedel, J. Org. Chem., 1994, 59, 6161 CrossRef CAS.
  6. J. R. Falck, R. K. Bhatt and J. Ye, J. Am. Chem. Soc., 1995, 117, 5973 CrossRef CAS.
  7. T. Takeda, K.-i. Matsunaga, Y. Kabasawa and T. Fujiwara, Chem. Lett., 1995, 771 CAS; S.-K. Kang, T. Yamaguchi, T.-H. Kim and P.-S. Ho, J. Org. Chem., 1996, 61, 9082 CrossRef CAS.
  8. J.-i. Yoshida, K. Tamao, A. Kurita and M. Kumada, Tetrahedron Lett., 1978, 1809 CrossRef CAS.
  9. J. F. Normant, Synthesis, 1972, 63 CrossRef CAS.
  10. For the preparation of 1,3-conjugated diynes, see A. S. Hay, J. Org. Chem., 1962, 27, 3320 Search PubMed; G. E. Jones, D. A. Kendrick and A. B. Holmes, Org. Synth., 1987, 65, 52 CrossRef CAS.
  11. Y. Hatanaka, K. Matsui and T. Hiyama, Tetrahedron Lett., 1989, 30, 2403 CrossRef CAS.
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