Copper(I)-catalysed homocoupling of organosilicon compounds: synthesis of biaryls, dienes and diynes

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Suk-Ku Kang, Tae-Hyun Kim and Sung-Jae Pyun


Abstract

Copper(I) iodide catalyses the homocoupling of aryl-, alkenyl- and alkynyl-substituted chloro- or fluoro-dimethylsilanes under mild conditions to afford biaryls, dienes and diynes, respectively.


References

  1. (a) U. Anton, C. Goltner and K. Mullen, Chem. Ber., 1992, 125, 2325 CAS; (b) D. S. Clelma, Nonlinear Optical Properties of Organic Molecules and Crystals, ed. J. Zyss, Academic Press, New York, 1983 Search PubMed; (c) V. D. Hunstman, The Chemistry of the Carbon–Carbon Triple Bond, ed. S. Patai, Wiley Interscience, London, 1978, p. 553 Search PubMed.
  2. (a) G. Solladie and G. Gottarelli, Tetrahedron, 1987, 43, 1425 CrossRef CAS; (b) A. E. Stiegman, E. Graham, K.-J. Perry, L. R. Khundkar, L.-T. Cheng and J. W. Perry, J. Am. Chem. Soc., 1991, 113, 7658 CrossRef CAS; (c) C. Fouquey, J.-M. Lehn and J. Malthete, J. Chem. Soc., Chem. Commun., 1987, 1424 RSC.
  3. (a) G. Bringmann, R. Walter and R. Weirich, Angew. Chem., Int. Ed. Engl., 1990, 29, 977 CrossRef and references cited therein; (b) C. Rosini, L. Franzini, A. Raffael and P. Salvadori, Synthesis, 1992, 6, 503 CrossRef.
  4. (a) R. A. Kretchner and R. Glowinski, J. Org. Chem., 1976, 41, 2661 CrossRef; (b) M. F. Semmelhack, P. M. Helquist and L. D. Jones, J. Am. Chem. Soc., 1971, 93, 5908 CrossRef CAS; (c) F. R. S. Clark, R. O. C. Norman and C. B. Thomas, J. Chem. Soc., Perkin Trans. 1, 1975, 121 RSC; (d) P. Banfield and P. M. Quan, Synthesis, 1978, 537 CrossRef CAS; (e) J. Yamashita, Y. Inoue, T. Kondo and H. Hashimoto, Chem. Lett., 1986, 407 CAS; (f) I. Colon and D. R. Kelsey, J. Org. Chem., 1986, 51, 2627 CrossRef CAS; (g) M. Zembayashi, K. Tamao, J. Yoshida and M. Kumada, Tetrahedron Lett., 1977, 47, 4089 CrossRef; (h) A. Jutand and A. Mosleh, Synlett, 1993, 568 CrossRef CAS; (i) M. Miura, H. Hashimoto, K. Itoh and M. Nomura, Chem. Lett., 1990, 459; (j) M. Iyoda, H. Otsuka, K. Sato, N. Nisato and M. Oda, Bull. Chem. Soc. Jpn., 1990, 63, 80 CAS; (k) M. Lourak, R. Vanderesse, Y. Fort and P. Caubere, J. Org. Chem., 1989, 54, 4840 CrossRef CAS; (l) H. Tanaka, A. Kosaka, S. Yamashita, K. Morisaki and S. Torii, Tetrahedron Lett., 1989, 30, 1261 CrossRef CAS.
  5. (a) S. Torii, H. Tanaka and K. Morisaki, Tetrahedron Lett., 1985, 26, 1655 CrossRef CAS; (b) C. Amatore and A. Jutand, Organometallics, 1988, 7, 2203 CrossRef CAS; (c) A. Jutand, S. Negri and A. Mosleh, J. Chem. Soc., Chem. Commun., 1992, 1729 RSC.
  6. P. E. Fanta, Synthesis, 1974, 9 CrossRef CAS.
  7. (a) R. C. Larock, J. Org. Chem., 1976, 41, 2241 CrossRef CAS and references cited therein; (b) R. C. Larock and J. C. Bernhardt, J. Org. Chem., 1977, 42, 1680 CrossRef CAS; (c) R. C. Larock and B. Riefling, J. Org. Chem., 1978, 43, 1468 CrossRef.
  8. (a) A. S. Hay, J. Org. Chem., 1962, 27, 3320 CrossRef CAS; (b) E. Valent, M. A. Pericas and F. Serratosa, J. Am. Chem. Soc., 1990, 112, 7405 CrossRef CAS.
  9. A. Pelter, K. Smith and M. Tabata, J. Chem. Soc., Chem. Commun., 1975, 857 RSC.
  10. The compounds 1a–1d and 1g–1h were prepared by a modified procedure reported in the literature. See, Y. Hatanaka, S. Fukushima and T. Hiyama, Tetrahedron, 1992, 48, 2113 Search PubMed.
  11. Y. Hatanaka, K.-I. Goda, Y. Okahara and T. Hiyama, Tetrahedron, 1994, 50, 8301 CrossRef CAS.
  12. Compounds 1e and 1f were prepared by the hydrosilylation of the corresponding terminal acetylene compounds with appropriate chlorosilanes followed by reaction with CuF2·2H2O. Hydrosilylation: see, (a) J. Yoshida, K. Tamao, M. Takahashi and M. Kumada, Tetrahedron Lett., 1978, 25, 2161 CrossRef; (b) K. Tamao, J. Yoshida, H. Yamamoto, T. Kakui, H. Matsumoto and M. Kumada, Organometallics, 1982, 1, 355 CrossRef CASFluorination: see, (c) K. Tamao, T. Kakui, J. Yoshida and M. Kumada, Tetrahedron, 1983, 39, 983 CrossRef CAS.
  13. Oxidative addition of organic halides to CuI salts has been described. See, (a) T. Cohen and I. Crested, J. Org. Chem., 1975, 40, 3649 CrossRef CAS; (b) T. Cohen and I. Crested, J. Am. Chem. Soc., 1976, 98, 748 CrossRef CAS.
  14. R. Damrauer and S. E. Danahey, Organometallics, 1986, 5, 1490 CrossRef CAS.
  15. The Merck Index, ed. M. Windholz, Merck, Rahway, NJ, 11th edn., 1989, p. 3314 and references cited therein Search PubMed.
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