Convenient and direct preparation of tertiary phosphines via nickel-catalysed cross-coupling

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

David J. Ager and Scott A. Laneman


Abstract

Nickel-catalysed cross-coupling of aryl sulfonates and aryl halides with chlorodiphenylphosphine and a reductant directly affords tertiary phosphines, which have application in a wide variety of asymmetric catalysis.


References

  1. D. J. Ager and M. B. East, Asymmetric Synthetic Methodology, CRC Press, Boca Raton, FL, 1995 Search PubMed .
  2. P. von Matt and A. Pfaltz, Angew. Chem., Int. Ed. Engl., 1993, 32, 566 CrossRef .
  3. P. von Matt, O. Loiseleur, G. Koch, A. Pfaltz, C. Lefeber, T. Feucht and G. Helmchen, Tetrahedron: Asymmetry, 1994, 5, 573 CrossRef CAS .
  4. B. M. Trost and R. C. Bunt, Angew. Chem., Int. Ed. Engl., 1996, 35, 99 CrossRef CAS .
  5. S. Akutagawa, Appl. Catal. A, 1995, 128, 171 CrossRef CAS .
  6. R. Noyori, Science, 1990, 248, 1194 CrossRef CAS .
  7. R. Noyori and H. Takaya, Acc. Chem. Res., 1990, 23, 345 CrossRef CAS .
  8. H. Takaya, T. Ohta and R. Noyori, in Asymmetric Hydrogenation, ed. I. Ojima, New York, NY, 1993 Search PubMed .
  9. W. Ude, S. Besecke, A. Riemann and G. Schroeder, Ger. Offen., 1986, DE 3425282 A1 Search PubMed .
  10. I.-Y. Wan, J. E. McGrath and T. Kashiwagi, ACS Symp. Ser., 1995, 599, 29 CAS .
  11. E. P. Kyba, M. C. Kerby and S. P. Rines, Organometallics, 1986, 5, 1189 CrossRef CAS .
  12. F. Langer, K. Puntener, R. Sturmer and P. Knochel, Tetrahedron: Asymmetry, 1997, 8, 715 CrossRef CAS .
  13. S. J. Coote, G. J. Dawson, C. G. Frost and J. M. J. Williams, Synlett, 1993, 509 CrossRef CAS .
  14. M. D. Fryzuk and B. Bosnich, J. Am. Chem. Soc., 1977, 99, 6262 CrossRef CAS .
  15. M. D. Fryzuk and B. Bosnich, J. Am. Chem. Soc., 1978, 100, 5491 CrossRef CAS .
  16. D. Cai, J. F. Payack, D. R. Bender, D. L. Hughes, T. R. Verhoeven and P. J. Reider, J. Org. Chem., 1994, 59, 7180 CrossRef CAS .
  17. S. E. Tunney and J. K. Stille, J. Org. Chem., 1987, 52, 748 CrossRef CAS .
  18. S. R. Gilbertson and G. W. Starkey, J. Org. Chem., 1996, 61, 2922 CrossRef CAS .
Click here to see how this site uses Cookies. View our privacy policy here.