Fully substituted cyclooctatetraenes assembled by the [4 + 4] cross coupling of two different diene units: a shunting strategy of Wilke’s metallacyclopentadiene coupling mechanism†

(Note: The full text of this document is currently only available in the PDF Version )

Yoshihiko Yamamoto, Tatsuya Ohno and Kenji Itoh


Abstract

The first regio- and chemo-selective synthesis of fully substituted cyclooctatetraenes from two or three different alkynes was achieved using the cross-coupling between 1,4-dicuprabuta-1,3-dienes and 1,4-diiodobuta-1,3-dienes.


References

  1. W. Reppe, O. Schlichting, K. Klager and T. Toepel, Justus Liebigs Ann. Chem., 1948, 560, 1 CAS.
  2. P. W. Jolly, in Comprehensive Organometallic Chemistry, ed. G. Wilkinson, F. G. A. Stone and E. W. Abel, Pergamon, London, 1982, vol. 8, p. 649 Search PubMed.
  3. G. Wilke, Pure Appl. Chem., 1978, 50, 677 CAS.
  4. The Ni-mediated homo-coupling of a 1,4-dilithiobuta-1, 3-diene was reported, see: C. J. Lawrie, K. P. Gable and B. K. Carpenter, Organometallics, 1989, 8, 2274 Search PubMed.
  5. CuCl-Mediated cross-coupling of zirconacyclopentadienes, see: T. Takahashi, M. Kotora, K. Kasai and N. Suzuki, Organometallics, 1994, 13, 4183 Search PubMed; T. Takahashi, R. Hara, Y. Nishihara and M. Kotora, J. Am. Chem. Soc., 1996, 118, 5154 CrossRef CAS; M. Kotora, C. Umeda, T. Ishida and T. Takahashi, Tetrahedron Lett., 1997, 38, 8355 CrossRef CAS; T. Takahashi, W.-H. Sun, Y. Liu, K. Nakajima and M. Kotora, Organometallics, 1998, 17, 3841 CrossRef CAS; T. Takahashi, Z. Xi, A. Yamazaki, Y. Liu, K. Nakajima and M. Kotora, J. Am. Chem. Soc., 1998, 120, 1672 CrossRef CAS.
  6. S. Yamaguchi, R.-Z. Jin, K. Tamao and F. Sato, J. Org. Chem., 1998, 63, 10 060 CrossRef CAS.
  7. F. Mohamadi and M. M. Spees, Organometallics, 1992, 11, 1398 CrossRef CAS.
  8. All new compound were characterized according to their 1H and 13C NMR and mass spectra CAS.
  9. O. Bastiansen, L. Hedberg and K. Hedberg, J. Chem. Phys., 1957, 27, 1311 Search PubMed.
  10. E. Negishi, S. J. Holmes, J. M. Tour, J. A. Miller, F. E. Cederbaum, D. R. Swanson and T. Takahashi, J. Am. Chem. Soc., 1989, 111, 3336 CrossRef CAS; Z. Xi, R. Hara and T. Takahashi, J. Org. Chem., 1995, 60, 4444 CrossRef CAS.
  11. Although only 1 equiv. is required, 2 equiv. of 11 were used to ensure the complete consumption of 7.
Click here to see how this site uses Cookies. View our privacy policy here.