Tetra-n-propylammonium perruthenate (TPAP)-catalysed oxidations of alcohols using molecular oxygen as a co-oxidant

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

Roman Lenz and Steven V. Ley


Abstract

Tetra-n-propylammonium perruthenate (TPAP) has been used as an efficient catalyst for the conversion of primary and secondary alcohols to the corresponding aldehydes and ketones under very mild aerobic conditions.


References

  1. T. F. Blackburn and J. Schwartz, J. Chem. Soc., Chem. Commun., 1977, 157 RSC.
  2. R. Tang, S. E. Diamond, N. Neary and F. Mares, J. Chem. Soc., Chem. Commun., 1978, 562 RSC.
  3. (a) M. Matsumoto and S. Ito, J. Chem. Soc., Chem. Commun., 1981, 907 RSC; (b) M. Matsumoto and N. Watanabe, J. Org. Chem., 1984, 49, 3436 CrossRef.
  4. Y. Hatanaka, T. Imamoto and M. Yokoyama, Tetrahedron Lett., 1983, 24, 2399 CrossRef CAS.
  5. M. F. Semmelhack, C. R. Schmid, D. A. Cortés and C. S. Chou, J. Am. Chem. Soc., 1984, 106, 3374 CrossRef CAS.
  6. J. Martin, C. Martin, M. Faraj and J.-M. Bregeault, Nouv. J. Chim., 1984, 8, 141 Search PubMed.
  7. C. Bilgrien, S. Davis and R. S. Drago, J. Am. Chem. Soc., 1987, 109, 3786 CrossRef CAS.
  8. T. Yamada and T. Mukaiyama, Chem. Lett., 1989, 519 CAS.
  9. J.-E. Bäckvall, R. L. Chowdhury and U. Karlsson, J. Chem. Soc., Chem. Commun., 1991, 473 RSC.
  10. T. Iwahama, S. Sakaguchi, Y. Nishiyama and Y. Ishii, Tetrahedron Lett., 1995, 36, 6923 CrossRef CAS.
  11. I. E. Markó, P. R. Giles, M. Tsukazaki, S. M. Brown and C. J. Urch, Science, 1996, 274, 2044 CrossRef CAS.
  12. W. P. Griffith, S. V. Ley, G. P. Whitcomb and A. D. White, J. Chem. Soc., Chem. Commun., 1987, 1625 RSC.
  13. S. V. Ley, J. Norman, W. P. Griffith and S. P. Marsden, Synthesis, 1994, 639 CrossRef.
  14. We thank Prof. I. E. Markó for communicating his independent studies prior to publication.
  15. B. Hinzen and S. V. Ley, J. Chem. Soc., Perkin Trans. 1, 1997, 1907 RSC.
Click here to see how this site uses Cookies. View our privacy policy here.