Synthesis of cross-conjugated trienes by dimerization of allenes with palladium-phenol catalyst

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Mieko Arisawa, Takumichi Sugihara and Masahiko Yamaguchi


Abstract

Cross-conjugated trienes were synthesized by dimerization of monosubstituted allenes in the presence of a catalyst system consisted of Pd2(dba)3, p-nitrophenol, and P(p-Tol)3.


References

  1. For example, W. J. Bailey, J. Economy and M. E. Hermes, J. Org. Chem., 1962, 27, 3295 Search PubMed; R. C. Blume, U.S. Pat. 3,860,669 CrossRef CAS; Chem. Abstr., 1975, 82, 172295j CrossRef CAS; U.S. Pat. 3,912,702 CrossRef CAS; Chem. Abstr., 1976, 84, 18546b CrossRef CAS.
  2. For example, U. Fleischer, W. Kutzelnigg, P. Lazzeretti and V. Mühlenkamp, J. Am. Chem. Soc., 1994, 116, 5298 Search PubMed.
  3. A review: H. Hopf, Angew. Chem., Int. Ed. Engl., 1984, 23, 948 Search PubMed Also see for examples, S. Kanemasa, H. Sakoh, E. Wada and O. Tsuge, Bull. Chem. Soc. Jpn., 1986, 59, 1869 CrossRef; G. Kaupp, H. Frey and G. Behmann, Chem. Ber., 1988, 121, 2127 Search PubMed; J. I. G. Cadogan, S. Cradock, S. Gillam and I. Gosney, J. Chem. Soc., Chem. Commun., 1991, 114 CAS; W. S. Trahanovsky and K. A. Koeplinger, J. Org. Chem., 1992, 57, 4711 CAS.
  4. M. Englert, P. W. Jolly and G. Wilke, Angew. Chem., Int. Ed. Engl., 1972, 11, 136 CrossRef CAS; D. J. Pasto, N.-Z. Huang and C. W. Eigenbrot, J. Am. Chem. Soc., 1985, 107, 3160 CrossRef CAS; D. J. Pasto and N.-Z. Huang, Organometallics, 1985, 4, 1386 CrossRef CAS.
  5. D. R. Coulson, J. Org. Chem., 1973, 38, 1483 CrossRef CAS; Y. Inoue, Y. Ohtsuka and H. Hashimoto, Bull. Chem. Soc. Jpn., 1984, 57, 3345 CAS.
  6. Yamamoto recently reported a Pd–acetic acid catalyst. M. Al-Masum, M. Meguro and Y. Yamamoto, Tetrahedron Lett., 1997, 38, 6071 Search PubMed; S. Kamijo, M. Al-Masum and Y. Yamamoto, Tetrahedron Lett., 1998, 39, 691 CrossRef CAS.
  7. Treatment of propa-1,2-diene with a Pd0 complex was reported to give dimeric π-allylpalladium. M. S. Lupin, J. Powell and B. L. Shaw, J. Chem. Soc. A, 1966, 1687 Search PubMed The compound could be another candidate for the intermediate of the present reaction.
  8. See the following for a related system using PhCHClMe/SnCl4: T. Higashimura, Y. Ishihama and M. Sawamoto, Macromolecules, 1993, 26, 744 Search PubMed.
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