Skip to main content

Organometallic reactions under phase transfer conditions

  • Chapter
Handbook of Phase Transfer Catalysis

Abstract

Homogeneous catalysis with metal complexes provides mild and selective routes to a variety of valuable chemicals from basic organic precursors. An important advantage of such routes over heterogeneous systems is that selectivity is achieved by changing the coordination sphere of the metal. However, the sensitivity of the catalyst or its precursor to air or moisture and problems associated with the separation of the organic products from the active catalyst often constitute a major economic barrier to commercial applications. One solution to the problem may be found in supported catalysts, which have long been known to combine the advantages of homogeneous and heterogeneous systems.

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

Access this chapter

Chapter
USD 29.95
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
eBook
USD 84.99
Price excludes VAT (USA)
  • Available as PDF
  • Read on any device
  • Instant download
  • Own it forever
Hardcover Book
USD 109.99
Price excludes VAT (USA)
  • Durable hardcover edition
  • Dispatched in 3 to 5 business days
  • Free shipping worldwide - see info

Tax calculation will be finalised at checkout

Purchases are for personal use only

Institutional subscriptions

Preview

Unable to display preview. Download preview PDF.

Unable to display preview. Download preview PDF.

Abbreviations

Aliquat 336:

methyltrioctylammonium chloride (technical grade)

bipy:

2,2′-bipyridine

Bz:

benzyl group

Bu:

butyl group

cod:

cyclooctadiene

CTAB:

cetyltrimethylammonium bromide

CPC:

cetylpyridinium chloride

C7h8 :

toluene

dba:

dibenzylideneacetone

dppm:

l,2-bis(diphenylphosphino)methane

diphos:

l,2-bis(diphenylphosphino)ethane

Hex:

hexyl group

OAc:

acetoxy group or acetate anion

o-phen:

1,10-phenanthroline

PEG:

poly(ethylene glycol)

py:

pyridine

TBAB:

tetrabutylammonium bromide

TDA-1:

tris(3,6-dioxaheptyl)amine

References

  1. Parshal, G.W. and Ittel, S.D. (1992) Homogeneous Catalysis, 2nd edn, Wiley, New York.

    Google Scholar 

  2. (a) Boudeville, M.A. and Des Abbayes, H. (1975) Tetrahedron Lett.,32, 2727; (b) Alper, H. and Des Roches, D. (1976) J. Organomet. Chem., 117, C44.

    Google Scholar 

  3. (a) Des Abbayes, H. (1985) Isr. J. Chem., 19, 249; (1987) Nouv. J. Chim., 11, 535; (b) Alper, H. (1984) in Fundamental Research Homogeneous Catalysis, Vol. 4 (eds M. Tsutsui and R. Ugo), Plenum Press, New York, p. 79; (c) Alper, H. (1981) Adv. Organomet. Chem., 19, 183; (d) Cassar, L. (1980) Ann. NY Acad Sci., 333, 208; (e) Cassar, L. (1977) in Fundamental Research Homogeneous Catalysis (eds M. Tsutsui and R. Ugo), Plenum Press, New York, p. 115; (0 Petrignani, J.F. (1989) in The Chemistry of the Metal-Carbon Bond, Vol. 5 (ed. F.R. Hartley), Chichester, pp. 63–106.

    Google Scholar 

  4. (a) Powell, J., Lough, A. and Wang, F. (1992), Organometallics, 11, 2289; (b) Powell, J., Kuksis, A., May, C.J. et al. (1981)J. Am. Chem. Soc., 103, 5941; (c) Powell, J., Gregg, M., Kuksis, A. and Meindl, P. (1983) J. Am. Chem. Soc., 105, 1064.

    Article  CAS  Google Scholar 

  5. McLain, S.J. (1983) J. Am. Chem. Soc., 105, 6355.

    Article  CAS  Google Scholar 

  6. Okano, T., Moriama, Y., Konishi, H. and Kiji, J. (1986) Chem. Lett., 1463.

    Google Scholar 

  7. (a) Okano, T., Iwahara, M., Suzuki, T. et al. (1986) Chem. Lett., 1467; (b) Okano, T., Iwahara, M., Konishi, H. and Kiji, J. (1988) J. Organomet. Chem., 346, 267.

    Article  CAS  Google Scholar 

  8. Sawamura, M., Nagata, H., Sakamoto, H. and Ito, Y. (1992), J. Am. Chem. Soc., 114, 2586.

    Article  CAS  Google Scholar 

  9. Okano, T., Harada, N. and Kiji, J. (1994) Chem. Lett., 1057.

    Google Scholar 

  10. (a) Lin, I.J.B., Lai, H.Y.C., Wu, S.C. and Hwan, L. (1986) J. Organomet. Chem., 304, C24; (b) Cheng, M.C., Peng, S.M., Lin, I.J.B. et al. (1987) J. Organomet. Chem., 327, 275;(c)Wu, R.F., Lin, I.J.B., Lee, G.H. et al (1990) Organometallics, 9, 126.

    Article  Google Scholar 

  11. Lin, I.J.B., Shy, H.C., Liu, C.W. et al. (1990) J. Chem. Soc., Dalton Trans., 2509.

    Google Scholar 

  12. Lin, I.J.B., Liu, C.W., Liu, L.-K. and Wen, Y.-S. (1992) Organometallics, 11, 1447.

    Article  CAS  Google Scholar 

  13. (a) Des Abbayes, H., Clement, J.-C., Laurent, P. et al. (1989) 7. Organomet. Chem., 359,205; (b) Tanguy, G., Weinberger, B. and Des Abbayes, H. (1985) J. Organomet. Chem., 280, C31; (c) Tanguy, G., Des Abbayes, H. and Clement, J.-C. (1986) J. Organomet. Chem., 314, C43.

    Article  Google Scholar 

  14. (a) Grushin, V.V., Akhrem, I.S. and Vol’pin, M.E. (1989) J. Organomet. Chem., 371,403; (b) Ioele, M., Ortaggi, G., Scarsella, M. and Sleiter, G. (1991) Polyhedron, 10, 2475.

    Article  CAS  Google Scholar 

  15. Grushin, V.V., Vymenits, A.B. and Vol’pin, M.E. (1990) J. Organomet. Chem., 382, 185.

    Article  CAS  Google Scholar 

  16. Grushin, V.V., Vymenits, A.B., Yanovsky, A.I. et al. (1991) Organometallics, 10,48.

    Article  CAS  Google Scholar 

  17. Chandiran, T. and Vancheesan, S. (1994) Proc. Indian Acad Sci. (Chem. Sci.), 106, 5.

    CAS  Google Scholar 

  18. Alper, H., Des Abbayes, H. and Des Roches, D. (1976) J. Organomet. Chem., 121, C31.

    Article  CAS  Google Scholar 

  19. Heck, R.F. (1968) J. Am. Chem. Soc., 90, 5518.

    Article  CAS  Google Scholar 

  20. (a) Jeffery, T. (1984) J. Chem. Soc., Chem. Commun., 1287; (b) Jeffery, T. (1994) Tetrahedron Lett., 35, 3051.

    Article  CAS  Google Scholar 

  21. Miura, M., Hashimoto, H., Itoh, K. and Nomura, M. (1989) Tetrahedron Lett., 30, 975.

    Article  CAS  Google Scholar 

  22. Andersson, C.-M. and Hallberg, A. (1988) J. Org. Chem., 53, 2112.

    Article  CAS  Google Scholar 

  23. Nye, S.A. and Potts, K.T. (1988) Synthesis, 375.

    Google Scholar 

  24. Jeffery, T. (1989) Tetrahedron Lett., 30, 2225.

    Article  CAS  Google Scholar 

  25. Gauthier, S. and Frechet, J.M.J. (1987) Synthesis, 383.

    Google Scholar 

  26. Greiner, A. (1989) Synthesis, 312.

    Google Scholar 

  27. Wang, J.-X., Hu, Y. and Cui, W. (1994) Synth. Commun., 24, 3261.

    Article  CAS  Google Scholar 

  28. Grushin, V.V. and Alper, H. (1991) Organometallics, 10, 1620.

    Article  CAS  Google Scholar 

  29. (a) Blum, J., Amer, I., Zoran, A. and Sasson, Y. (1983) Tetrahedron Lett., 24, 4139; (b) Amer, I., Amer, H. and Blum, J. (1986) J. Mol Catal, 34, 221.

    Article  CAS  Google Scholar 

  30. Amer, I., Amer, H., Ascher, R. and Blum, J. (1987) J. Mol. Catal., 39, 185.

    Article  CAS  Google Scholar 

  31. Blum, J., Amer, I., Vollhardt, K.P.C. et al. (1987) J. Org. Chem., 52, 2804.

    Article  CAS  Google Scholar 

  32. Falicki, S. and Alper, H. (1988) Organometallics, 1, 2548.

    Article  Google Scholar 

  33. Amer, I., Bravdo, T. and Blum, J. (1987) Tetrahedron Lett., 28, 1321.

    Article  CAS  Google Scholar 

  34. Landre, F.D., Richard, D., Draye, M. et al. (1994) J. Catal., 147, 214.

    Article  CAS  Google Scholar 

  35. (a) Januszkiewicz, K.R. and Alper H. (1983) Organometallics, 2, 1055; (b) Zahalka, H.A. and Alper, H. (1985) Organometallics, 5, 1909.

    Article  CAS  Google Scholar 

  36. Sasson, Y., Zoran, A. and Blum, J. (1979) J. Mol. Catal., 6, 289; (b) Sasson, Y., Zoran, A. and Blum, J. (1981) J. Mol. Catal., 11, 293; (c) Alper, H. and Hachem, K. (1980) J. Org. Chem., 45, 2269; (d) Alper, H. and Hachem, K. (1981) Transition Met. Chem., 6, 219.

    Article  CAS  Google Scholar 

  37. Amer, I., Orshav, V. and Blum, J. (1988) J. Mol. Catal., 45,207.

    Article  CAS  Google Scholar 

  38. Amer, I., Blum, J. and Vollhardt, K.P.C. (1990) J. Mol. Catal., 60,323.

    Article  CAS  Google Scholar 

  39. Amer, I., Bernstein, T., Eisen, M. et al. (1990) J. Mol. Catal., 60,313.

    Article  CAS  Google Scholar 

  40. Badrieh, Y., Blum, J., Amer, I. and Vollhardt, K.P.C. (1991) J. Mol Catal, 66, 295.

    Article  CAS  Google Scholar 

  41. Setty-Fichman, M., Blum, J., Sasson, Y. and Eisen, M. (1994) Tetrahedron Lett., 35, 781.

    Article  CAS  Google Scholar 

  42. (a) Rosenfeld, A., Avnir, D. and Blum, J. (1993) J. Chem. Soc., Chem. Commun., 583; (b) Rosenfeld, A., Blum, J., Polak, N. et al. (1996) J. Mol. Catal., 107, 217.

    Article  Google Scholar 

  43. Goldberg, Y. (1992) Phase Transfer Catalysis: Selected Problems and Applications, Gordon and Breach, New York.

    Google Scholar 

  44. Amaratunga, S. and Alper, H. (1995) J. Organomet. Chem., 488, 25.

    Article  CAS  Google Scholar 

  45. Badrieh, Y., Greenwald, A., Schuman, H. and Blum, J. (1992) Chem. Ber., 125, 667.

    Article  CAS  Google Scholar 

  46. Badrieh, Y., Schuman, H. and Blum, J. (1994) J. Mol. Catal., 90, 231.

    Article  CAS  Google Scholar 

  47. Des Abbayes, H. and Alper, H. (1977) J. Am. Chem. Soc., 99, 98.

    Article  Google Scholar 

  48. (a) Tanguy, G., Weinberger, B. and Des Abbayes, H. (1984) Tetrahedron Lett., 25, 5529; (b) Tanguy, G., Laurent, P. and Des Abbayes, H. (1985) J. Chem. Soc., Chem. Commun., 1755.

    Article  CAS  Google Scholar 

  49. Des Abbayes, H., Tanguy, G., Laurent, P. et al. (1988) Organometallics, 1, 2293.

    Article  Google Scholar 

  50. Cassar, L., Foa, M. and Gardano, A. (1976) J. Organomet. Chem., 121, C55.

    Article  CAS  Google Scholar 

  51. (a) Grushin, V.V. and Alper, H. (1993) Organometallics, 12, 1890; (b) Grushin, V.V. and Alper, H. (1992) J. Chem. Soc., Chem. Commun., 611.

    Article  CAS  Google Scholar 

  52. Galamb, V., Gopal, M. and Alper, H. (1983) Organometallics, 2, 801.

    Article  CAS  Google Scholar 

  53. Li, P. and Alper, H. (1986) J. Org. Chem., 51,4354.

    Article  CAS  Google Scholar 

  54. Okano, T., Harada, N. and Kiji, J. (1992) Bull. Chem. Soc. Jpn., 65, 1741.

    Article  CAS  Google Scholar 

  55. Arzoumanian, H., Choukrad, M. and Nuel, D. (1993) J. Mol. Catal., 85, 287.

    Article  CAS  Google Scholar 

  56. Des Abbayes, H., Buloup, A. and Tanguy, G. (1983) Organometallics, 2, 1730.

    Article  Google Scholar 

  57. Amer, I. (1994) Inorg. Chim. Acta, 216, 97.

    CAS  Google Scholar 

  58. Gambarotta, S. and Alper, H. (1981) J. Organomet. Chem., 212, C23.

    Article  CAS  Google Scholar 

  59. Hu, Y., Wang, J.-X. and Cui, W. (1994) Synth. Commun., 24, 1743.

    Article  CAS  Google Scholar 

  60. Brunet, J.J., Sidot, C. and Cambere, D. (1983) J. Org. Chem.,48, 1166.

    Article  CAS  Google Scholar 

  61. (a) Miura, M., Akase, F., Shinohara, M. and Nomura, M. (1987) J. Chem. Soc., Perkin Trans 1, 1021; (b) Miura, M., Akase, F. and Nomura, M. (1986) J. Chem. Soc., Chem. Commun., 241.

    Article  Google Scholar 

  62. Lee, J.-T. and Alper, H. (1990) Organometallics, 9, 3064.

    Article  CAS  Google Scholar 

  63. Arzoumanian, H., Alper, H., Petrignani, J.F. and Saldana-Maldonado, M. (1985) J. Chem. Soc., Chem. Commun., 340.

    Google Scholar 

  64. Alper, H., Eisenstat, A. and Satyanarayana, N. (1990) J. Am. Chem. Soc., 112, 7060.

    Article  CAS  Google Scholar 

  65. Alper, H. and Calet, S. (1988) Tetrahedron Lett., 29, 1763.

    Article  CAS  Google Scholar 

  66. Alper, H. and Calet, S. (1987) Organometallics, 6, 1625.

    Article  Google Scholar 

  67. Roberto, D. and Alper, H. (1990) Organometallics, 9, 1245.

    Article  CAS  Google Scholar 

  68. Vasapollo, G. and Alper, H. (1988) Tetrahedron Lett., 29, 5113.

    Article  CAS  Google Scholar 

  69. Foa’, M. and Cassar, L. (1979) Gazz. Chim. Ital., 109, 619.

    Google Scholar 

  70. Joo’, F. and Alper, H. (1985) Organometallics, 4, 1775.

    Article  Google Scholar 

  71. Amer, I. and Alper, H. (1988) J. Org. Chem., 53, 5147.

    Article  CAS  Google Scholar 

  72. Amer, I. and Alper, H. (1989) J. Am. Chem. Soc., 111, 927.

    Article  CAS  Google Scholar 

  73. Grushin, V.V. and Alper, H. (1991) Tetrahedron Lett., 32, 3349.

    Article  CAS  Google Scholar 

  74. Amer, I., Vasapollo, G. and Alper, H. (1989) Tetrahedron Lett., 30, 2615.

    Article  Google Scholar 

  75. Vasapollo, G. and Alper, H. (1989) Tetrahedron Lett., 30, 2617.

    Article  Google Scholar 

  76. Younis, K. and Amer, I. (1994) Organometallics, 13, 3120.

    Article  CAS  Google Scholar 

  77. Amer, J. and Alper, H. (1990) J. Organomet. Chem., 383, 573.

    Article  CAS  Google Scholar 

  78. Lee, J.-T. and Alper, H. (1991) Tetrahedron Lett., 32, 1769.

    Article  CAS  Google Scholar 

  79. Arzoumanian, H., Jean, M., Nuel, D. et al. (1995) Organometallics, 14, 5438.

    Article  CAS  Google Scholar 

  80. Satyanarayana, N., Alper, H. and Amer, I. (1990) Organometallics, 9, 284.

    Article  CAS  Google Scholar 

  81. Arzoumanian, H., Nuel, D., Cochini, F. and Rosas, N. (1993) Organometallics, 12, 1871.

    Article  CAS  Google Scholar 

  82. Arzoumanian, H., Nuel, D., Cochini, F. et al. (1993) Organometallics, 12, 1871.

    Article  CAS  Google Scholar 

  83. Roso-Levi, G. and Amer, I. (1996) J. Mol. Catal, 106, 51.

    Article  CAS  Google Scholar 

  84. Satyanarayana, N. and Alper, H. (1991) Organometallics, 10, 804.

    Article  CAS  Google Scholar 

  85. (a) Januszkiewicz, K. and Alper, H. (1983) Tetrahedron Lett., 24, 5159; (b) Januszkiewicz, K. and Alper, H. (1983) Tetrahedron Lett., 24, 5163; (c) Januszkiewicz, K., Smith, D.J.H. and Alper, H. (1985) Tetrahedron Lett., 26, 2263.

    Article  CAS  Google Scholar 

  86. Ishii, Y., Yamawaki, K., Ura, T. et al. (1988) J. Org. Chem., 53, 3587.

    Article  CAS  Google Scholar 

  87. Ballistreri, F.P., Chiacchio, U., Rescifina, A. et al. (1992) Tetrahedron, 48, 8677.

    Article  CAS  Google Scholar 

  88. Fort, Y., Olszewski-Ortar, A. and Caubere, P. (1992) Tetrahedron, 48, 5099.

    Article  CAS  Google Scholar 

  89. Muzart, J. and Ajjou, A.N. (1991) Synth. Commun., 21, 575.

    Article  CAS  Google Scholar 

  90. Rao, K.H. and Rao, M.B. (1991) J. Indian Chem. Soc., 68, 132.

    CAS  Google Scholar 

Download references

Authors

Editor information

Editors and Affiliations

Rights and permissions

Reprints and permissions

Copyright information

© 1997 Chapman & Hall

About this chapter

Cite this chapter

Amer, I. (1997). Organometallic reactions under phase transfer conditions. In: Sasson, Y., Neumann, R. (eds) Handbook of Phase Transfer Catalysis. Springer, Dordrecht. https://doi.org/10.1007/978-94-009-0023-3_10

Download citation

  • DOI: https://doi.org/10.1007/978-94-009-0023-3_10

  • Publisher Name: Springer, Dordrecht

  • Print ISBN: 978-0-7514-0258-2

  • Online ISBN: 978-94-009-0023-3

  • eBook Packages: Springer Book Archive

Publish with us

Policies and ethics