Cobalt(II) Chloride. Aluminium Promoted Allylation of Aldehydes with Allylic Halides†

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Rahat H. Khan and Turga S. R. Prasada Rao


Abstract

In the presence of cobalt(II) chloride–metallic aluminium, allylic halides react with aldehydes at room temperature in tetrahydrofuran–water to afford the corresponding alcohols in high yields.


References

  1. Y. Yamamoto and N. Asao, Chem. Rev., 1993, 93, 2207 CrossRef CAS; T. M. Cokley, R. L. Marshall, A. McCluskey and D. J. Young, Tetrahedron Lett., 1996, 37, 1905 CrossRef CAS; A. Yanagisawa, H. Nakashima, A. Ishiba and H. Yamamoto, J. Am. Chem. Soc., 1996, 118, 4722 CrossRef CAS; K. Sugimoto, S. Aoyagi and C. Kibayashi, J. Org. Chem., 1997, 62, 2322 CrossRef CAS.
  2. J. A. Marshall and K. W. Hinkle, J. Org. Chem., 1996, 61, 4247 CrossRef CAS.
  3. J. S. Carey, T. S. Coutler, D. J. Hallet, R. J. Maguire, A. H. McNeil, S. J. Stanway, A. Teerawutgulrag and E. J. Thomas, Pure Appl. Chem., 1996, 68, 707 CAS.
  4. S. Ahmad and J. Iqbal, J. Chem. Soc., Chem. Commun., 1987, 692 RSC.
  5. For other catalytic reactions of cobalt(II) chloride see: J. Marquet and M. Moreno-Manas, Chem. Lett., 1981, 173 Search PubMed; H. Matsuda and H. Kanai, Chem. Lett., 1981, 395 CAS; J. Iqbal, B. Bhatia and N. K. Nayyar, Chem. Rev., 1994, 94, 519 CAS; M. Mukhopadhyay and J. Iqbal, J. Org. Chem., 1997, 62, 1843 CrossRef CAS.
  6. Other similar allylation of carbonyl compounds in aqueous media has been reported to be a Borbier-type reaction: J. Nokami, I. Otera, T. Sudo and R. Okawara, Organometallics, 1983, 2, 191 Search PubMed; C. Petrier, J. Eihorn and J. L. Luche, Tetrahedron Lett., 1985, 26, 1449 CrossRef CAS; C. Petrer and J. L. Luche, J. Org. Chem., 1985, 50, 910 CrossRef; K. Uneyama, N. Karmaki, A. Moriya and S. Torri, J. Org. Chem., 1985, 50, 5396 CrossRef CAS; K. Uneyama, H. Nambu and S. Torri, Tetrahedron Lett., 1986, 27, 2395 CrossRef CAS; A. Yanagisawa, H. Inoue, M. Morodome and H. Yamamoto, J. Am. Chem. Soc., 1993, 115, 10 356 CrossRef CAS; A. Lubineau, J. Auge and Y. Queneau, Synthesis, 1994, 741 CrossRef CAS; M. B. Isaac and T. H. Chan, Tetrahedron Lett., 1995, 36, 8957 CrossRef CAS.
  7. G. L. Smith and K. J. Voorhees, J. Org. Chem., 1970, 35, 2182 CrossRef CAS.
  8. M. F. Lipton and R. H. Shapiro, J. Org. Chem., 1978, 43, 1409 CrossRef CAS.
  9. Y. Kanagawa, Y. Nishiyama and Y. Ishii, J. Org. Chem., 1992, 57, 6988 CrossRef CAS.
  10. S. R. Wilson and M. E. Guazzar, J. Org. Chem., 1989, 54, 3087 CrossRef CAS.
  11. D. Abenhaim, E. Henry Basch and P. Freon, Bull. Soc. Chim. Fr., 1969, 11, 4038.
  12. T. Mandai, J. Nokami, Y. Yano, Y. Yoshinaga and J. Otera, J. Org. Chem., 1984, 49, 172 CrossRef CAS.
  13. K. Sugimoto, S. Ayoyagi and C. Kibayashi, J. Org. Chem., 1997, 62, 2322 CrossRef CAS.
  14. M. Wada, H. Ohki and K. Y. Akiba, Tetrahedron Lett., 1986, 27, 4771 CrossRef CAS.
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