Skip to main content
SpringerLink
Log in

Nickel-catalyzed cross-coupling of bromophenols with Grignard reagents in the solid phase synthesis

  • Published:
Molecular Diversity Aims and scope Submit manuscript

Abstract

Polymer-bound substituted bromophenols were found to readily undergo a Ni(0)-catalyzed cross-coupling reaction with Grignard reagents to give a variety of substituted phenols and hydroquinones, after cleavage from the support, in moderate to high yields. The requisite bromophenol derivatives, which were prepared from the corrresponding phenols and hydroquinone using BTMA Br3 or TBA Br3, were attached to the solid support by the Mitsunobu reaction.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. Yu, K.L., Deshpande, M.S. and Vyas, D.M., Tetrahedron Lett., 35 (1994) 8919–8922.

    Google Scholar 

  2. Hiroshige, M., Hauske, J.R. and Zhou, P., Tetrahedron Lett., 36 (1995) 4567–4570.

    Google Scholar 

  3. Pop, I.E., Dhallulin, C.F., Deprez, B.P., and Melnyk, P.C., Lippens, G.M. and Tartar, A.L., Tetrahedron, 52 (1996) 12209–12222.

    Google Scholar 

  4. Yun, W.Y. and Mohan, R., Tetrahedron Lett., 37 (1996) 7189–7192.

    Google Scholar 

  5. Akaji, K. and Kiso, Y., Tetrahedron Lett., 38 (1997) 5185–5188.

    Google Scholar 

  6. Arumugam, V., Routledge, A., Abell, C. and Balasubramanjan, S., Tetrahedron Lett., 38 (1997) 6473–6476.

    Google Scholar 

  7. Bolton, G.L. and Hodges, J.C., J. Comb. Chem., 1 (1999) 130–133.

    Google Scholar 

  8. Kulkarni, B.A. and Ganesan, A., J. Comb. Chem., 1 (1999) 373–378.

    Google Scholar 

  9. Deshpande, M.S., Tetrahedron Lett., 35 (1994) 5613–5614.

    Google Scholar 

  10. Plunkett, M.J. and Ellman, J.A., J. Am. Chem. Soc., 117 (1995) 3306–3307.

    Google Scholar 

  11. Forman, F.W. and Sucholeiki, I., J. Org. Chem., 60 (1995) 523–528.

    Google Scholar 

  12. Chamoin, S., Houldsworth, S. and Snieckus, V., Tetrahedron Lett., 39 (1998) 4175–4178.

    Google Scholar 

  13. Nicolaou, K.C., Winssinger, N., Pastor, J. and Murphy, F., Angew. Chem. Int. Ed. Engl., 37 (1998) 2534–2537.

    Google Scholar 

  14. Sieber, F., Wentworth, P. and Janda, K.D., J. Comb. Chem., 1 (1999) 540–546.

    PubMed  Google Scholar 

  15. Lee, C.Y. and Hanson, R.N., Tetrahedron, 56 (2000) 1623–1629.

    Google Scholar 

  16. Kraxner, J., Arlt, M. and Gmeiner, P., Synlett., (2000) 125–127.

  17. Frenette, R. and Friesen, R.W., Tetrahedron Lett., 35 (1994) 9177–9180.

    Google Scholar 

  18. Han, Y.X., Walker, S.D. and Young, R.N., Tetrahedron Lett., 37 (1996) 2703–2706.

    Google Scholar 

  19. Larhed, M., Lindeberg, G. and Hallberg, A., Tetrahedron Lett., 37 (1996) 8219–8222.

    Google Scholar 

  20. Guiles, J.W., Johnson, S.G. and Murray, W.V., J. Org. Chem., 61 (1996) 5169–5171.

    Google Scholar 

  21. Piettre, S.R. and Baltzer, S., Tetrahedron Lett., 38 (1997) 1197–1200.

    Google Scholar 

  22. Ruhland, B., Bombrun, A. and Gallop, M.A., J. Org. Chem., 62 (1997) 7820–7826.

    Google Scholar 

  23. Lorsbach, B.A., Bagdanoff, J.T., Miller, R.B. and Kurth, M.J., J. Org. Chem., 63 (1998) 2244–2250.

    Google Scholar 

  24. Chamoin, S., Houldswroth, S., Kruse, C.G., Bakker, W.I. and Snieckus, V., Tetrahedron Lett., 39 (1998) 4179–4182.

    Google Scholar 

  25. Blake, A.J., Cooke, P.A., Doyle, K.J., Gair, S. and Simpkins, N.S., Tetrahedron Lett., 39 (1998) 9093–9096.

    Google Scholar 

  26. Li, W. and Burgess, K., Tetrahedron Lett., 40 (1999) 6527–6530.

    Google Scholar 

  27. Gravel, M., Berube, C.D. and Hall, D.G., J. Comb. Chem., 2 (2000) 228–231.

    PubMed  Google Scholar 

  28. Guiles, J.W., Johnson, S.G. and Murray, W.V., J. Org. Chem., 61 (1996) 5169–5171. (b) Jang, S.B., Tetrahedron Lett., 38 (1997) 1793–1796.

    Google Scholar 

  29. To our knowledge, only one example of the cross-coupling with alkylzinc iodides has been reported in the solid phase nickel-catalyzed cross-coupling reaction: Jensen, A.E., Dohle, W. and Knochel, P., Tetrahedron, 56 (2000) 4197–4201.

    Google Scholar 

  30. Seo, Y.S., Yun, H.S. and Park, K.Y., Bull. Korean Chem. Soc., 20 (1999) 1345–1347.

    Google Scholar 

  31. Kajigaeshi, S., Kakinami, T., Tokiyama, H., Hirakawa, T. and Okamoto, T., Chem. Lett., (1987) 627.

  32. Kajigaeshi, S., Kakinami, T., Okamoto, T., Nakamura, H. and Fujikawa, M., Bull. Chem. Soc. Jpn., 60 (1987) 4187.

    Google Scholar 

  33. Feinberg, R.S. and Merrifield, R.B., Tetrahedron, 30 (1974) 3209–3212.

    Google Scholar 

  34. Wang, S., J. Am. Chem. Soc., 95 (1973) 1328–1333.

    PubMed  Google Scholar 

  35. Richter, L.S. and Gadek, T.R., Tetrahedron Lett., 35 (1994) 4705–4706.

    Google Scholar 

  36. Rano, T.A. and Chapman, K.T., Tetrahedron Lett., 36 (1995) 3789–3792.

    Google Scholar 

  37. Tsunoda, T., Otsukka, J., Yamamiya, Y. and Ito, S., Chem. Lett. (1994) 539.

  38. Krchnak, V., Flegelova, Z., Weichsel, A.S. and Lebl, M., Tetrahedron Lett., 36 (1995) 6193–6196.

    Google Scholar 

  39. Castro, J.L., Matassa, V.G. and Ball, R.G., J. Org. Chem., 59 (1994) 2289–2291.

    Google Scholar 

  40. Campbell, D.A. and Bermak, J.C., J. Am. Chem. Soc., 116 (1994) 6039–6040.

    Google Scholar 

  41. Norman, T.C., Gray, N.S., Koh, J.T. and Schultz, P.G., J. Am. Chem. Soc., 118 (1996) 7430–7431.

    Google Scholar 

  42. Valerio, R.M., Bray, A.M. and Patsiouras, H., Tetrahedron Lett., 27 (1996) 3019–3022.

    Google Scholar 

  43. Sarshar, S., Siev, D. and Mjalli, A.M.M., Tetrahedron Lett., 37 (1996) 835–838.

    Google Scholar 

  44. Reddy, M.P. and Voelker, P.J., Int. J. Pept. Protein Res., 31 (1988) 345–3.

    Google Scholar 

Download references

Author information

Authors and Affiliations

  1. School of Chemical Engineering, Seoul National University, Seoul, 151-742, Korea

    Heon Park, Sang-Il Yoon & Yoon-Sik Lee

  2. Department of Chemical Engineering, Chung-Ang University, Seoul, 156-756, Korea

    Kwangyong Park

Authors
  1. Heon Park
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sang-Il Yoon
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Kwangyong Park
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yoon-Sik Lee
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yoon-Sik Lee.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Park, H., Yoon, SI., Park, K. et al. Nickel-catalyzed cross-coupling of bromophenols with Grignard reagents in the solid phase synthesis. Mol Divers 5, 57–60 (2000). https://doi.org/10.1023/A:1013853421101

Download citation

  • Issue Date:

  • DOI: https://doi.org/10.1023/A:1013853421101

Search

Navigation