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1887
Volume 34, Issue 1
  • ISSN: 0032-1400

Abstract

Phase transfer catalysis is an elegant method for ameliorating the reaction conditions of many organic reactions and improving yields and selectivities. A review is presented of the role and scope of the compounds of the platinum group metals as cocatalysts under phase transfer conditions. The most useful improvements have been found in reactions involving the formation of carbon-carbon bonds such as in carbonylations and vinylations, and in reductions with formate.

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1990-01-01
2024-12-30
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References

  1. H. Schnell, Angew. Chem., 1956, 68, 633 [Google Scholar]
  2. C. M. Starks, Isr. J. Chem., 1985, 26, 211 [Google Scholar]
  3. C. M. Starks, “Phase-Transfer Catalysis”, ed. C. M. Starks, 1985, 1 [Google Scholar]
  4. J. Dockx, Synthesis, 1973, 441 [Google Scholar]
  5. M. Makosza, Pure Appl. Chem., 1975, 43, 439 [Google Scholar]
  6. A. Brandstrom, “Preparative Ion Pair Extraction”, Apotekarsocietet, Stockholm, 1976 [Google Scholar]
  7. E. V. Dehmlow, Angew. Chem., Int. Ed. Engl., 1977, 16, 493 [Google Scholar]
  8. W. P. Weber, G. W. Gokel, “Phase Transfer Catalysis in Organic Synthesis”, Springer Verlag, Berlin, 1977 [Google Scholar]
  9. A. Brandstrom, Adv. Phys. Org. Chem., 1977, 15, 267 [Google Scholar]
  10. M. Makosza, Russ. Chem. Rev., 1977, 46, 1151 [Google Scholar]
  11. C. M. Starks, C. Liotta, “Phase Transfer Catalysis”, Academic Press, New York, 1978 [Google Scholar]
  12. J. M. Lehn, Acc. Chem. Res., 1978, 11, 49 [Google Scholar]
  13. J. M. Mcintosh, J. Chem. Ed., 1978, 55, 235 [Google Scholar]
  14. G. W. Gokel, W. P. Weber, J. Chem. Ed., 1978, 55, 350 [Google Scholar]
  15. W. P. Weber, G. W. Gokel, J. Chem. Ed., 1978, 55, 429 [Google Scholar]
  16. M. Makosza, “ Survey of Progress in Chemistry”, Vol IX, Academic Press, New York, 1979 [Google Scholar]
  17. W. E. Keller, “Compendium of Phase-Transfer Reactions and Related Synthetic Methods”, Fluka, Switzerland, 1979 [Google Scholar]
  18. L. Lindblom, M. Elander, Pharm. Technol., 1980, (10), 59 [Google Scholar]
  19. B. Reuben, K. Sjoberg, Chemtech, 1981, 315 [Google Scholar]
  20. P. Cocagne, J. Elguero, R. Gallo, Heterocycles, 1983, 20, 1379 [Google Scholar]
  21. E. V. Dehmlow, S. S. Dehmlow, “Phase Transfer Catalysis”, Verlag Chemie, Weinheim, 1983 [Google Scholar]
  22. E. D’Incan, P. Viout, R. Gallo, Isr. J. Chem., 1985, 26, 277 [Google Scholar]
  23. H. H. Freedman, Pure Appl. Chem., 1986, 58, 857 [Google Scholar]
  24. L. Cassar, Ann. N.Y. Acad. Sci., 1980, 333, 208 [Google Scholar]
  25. H. Alper, Adv. Organomet. Chem., 1981, 19, 183 [Google Scholar]
  26. H. Alper, Fundam. Res. Homogeneous Catal., 1984, 4, 79 [Google Scholar]
  27. H. Des Abbaye, Isr. J. Chem., 1985, 26, 249 [Google Scholar]
  28. H. Alper, Prep. Am. Chem. Soc., Div. Pet. Chem., 1985, 30, 364 [Google Scholar]
  29. H. Alper, “Phase-Transfer Catalysis”, ed. C. M. Starks, 1985, 8 [Google Scholar]
  30. H. Alper, K. Hashem, J. Heveling, Organometallics, 1982, 1, 775 [Google Scholar]
  31. S. Zhang, S. Xiao, M. Ran, H. Dai, Fenzi Cuihua, 1987, 1, 115; CA 109:756531 [Google Scholar]
  32. H. Arzoumanian, G. Buono, M’Barek Choukrad, J. F. Petrignani, Organometallics, 1988, 7, 59 [Google Scholar]
  33. V. Galamb, H. Alper, J. Chem. Soc., Chem. Commun., 1983, 88 [Google Scholar]
  34. L. Cassar, M. Foa, A. Gardano, J. Organomet. Chem., 1976, 121, C55 [Google Scholar]
  35. V. Galamb, M. Gopal, H. Alper, Organometallics, 1983, 2, 801 [Google Scholar]
  36. V. Galamb, H. Alper, Transition Met. Chem., 1983, 8, 271 [Google Scholar]
  37. B. M. Choudary, P. N. Reddy, B. Ashok, Appl. Catal., 1987, 32, 357 [Google Scholar]
  38. I. Pri-Bar, H. Alper, J. Org. Chem., 1989, 54, 36 [Google Scholar]
  39. J. E. Hallgren, G. M. Lucas, J. Organomet. Chem., 1981, 212, 135 [Google Scholar]
  40. J. E. Hallgren, U.S. Patent 4, 361, 519, 1980 [Google Scholar]
  41. R. T. Smith, R. K. Unger, L. J. Sanderson, M. C. Baird, Ann. N.Y. Acad. Sci., 1983, 415, 253 [Google Scholar]
  42. H. Bahnnann, B. Cornils, W. Konkol, W. Lipps, German Offen. 3,412, 335, 1985 [Google Scholar]
  43. M. J. H. Russell, Platinum Metals Rev., 1988, 32, (4), 179 [Google Scholar]
  44. E. G. Kuntz, Chemtech, 1987, 17, 570 [Google Scholar]
  45. R. F. Heck, Org. React., 1982, 27, 345; [Google Scholar]
  46. “Palladium Reagents in Organic Synthesis”, Academic Press, London, 1985 [Google Scholar]
  47. T. Jeffery, J. Chem. Soc, Chem. Commun., 1984, 1287 [Google Scholar]
  48. T. Jeffery, Tetrahedron Lett., 1985, 26, 2667 [Google Scholar]
  49. T. Jeffery, Synthesis, 1987, 70 [Google Scholar]
  50. R. Benhaddou, S. Czernecki, G. Ville, A. Zegar, Organometallics, 1988, 7, 2435 [Google Scholar]
  51. R. Rossi, A. Carpita, M. G. Quirici, M. L. Gaudenzi, Tetrahedron, 1982, 38, 631 [Google Scholar]
  52. H. A. Zahalka, K. Januskiewicz, H. Alper, J. Mol. Catal, 1986, 35, 249 [Google Scholar]
  53. K. Januskiewicz, H. Alper, Tetrahedron Lett., 1983, 24, 5163 [Google Scholar]
  54. E. S. Gore, Platinum Metals Rev., 1983, 27, (3), 111 [Google Scholar]
  55. E. S. Gore, “Chemistry of the Platinum Group Metals: Recent Developments”, ed. by F. R. Hartley, Elsevier, Amsterdam, to be published [Google Scholar]
  56. P. H. J. Carlsen, T. Katsuki, V. S. Martin, K. B. Sharpless, J. Org. Chem., 1981, 46, 3936 [Google Scholar]
  57. K. Januskiewicz, H. Alper, Tetrahedron Lett., 1983, 24, 5159 [Google Scholar]
  58. A. Harada, Y. Hu, S. Takahashi, Chem. Lett. Jpn., 1986, 2083 [Google Scholar]
  59. H. Alper, K. Januskiewicz, D. J. H. Smith, Tetrahedron Lett., 1985, 26, 2263 [Google Scholar]
  60. F. Matsuda, K. Kato, Japanese Appl. 61/68439, 1986 [Google Scholar]
  61. S. G. Kukes, T. K. Shioyama, U.S. Patent 4,448, 892, 1984 [Google Scholar]
  62. W. H. Clement, C. M. Selwitz, J. Org. Chem., 1964, 29, 241 [Google Scholar]
  63. T. P. Murtha, T. K. Shioyama, U.S. Patent 4,434,082, 1984 [Google Scholar]
  64. J. Tsuji, Org. Synth., 1984, 62, 9 [Google Scholar]
  65. C. M. Starks, P. W. Washecheck, U.S. Patent 3,547,962, 1970 [Google Scholar]
  66. T. A. Foglia, P. A. Barr, A. J. Malloy, J. Am. OU Chem. Soc., 1977, 54, 858A [Google Scholar]
  67. G. Barak, Y. Sasson, J. Chem. Soc, Chem. Commun., 1987, 1266 [Google Scholar]
  68. J. C. Dobson, W. K. Seek, T. J. Meyer, In-org. Chem., 1986, 25, 1514 [Google Scholar]
  69. Y. Sasson, G. D. Zappi, R. Neumann, J. Org. Chem., 1986, 51, 2880 [Google Scholar]
  70. G. Barak, Y. Sasson, J. Chem. Soc, Chem. Commun., 1988, 637 [Google Scholar]
  71. E. S. Olson, B. W. Farnum, Prep. Pap. ACS., Div. Fuel Chem., 1981, 26, 60 [Google Scholar]
  72. P. E. Morris, D. E. Kiely, J. Org. Chem., 1987, 52, 1149 [Google Scholar]
  73. Y. Yamamoto, H. Suzuki, Y. Moro-oka, Tetrahedron Lett., 1985, 26, 2107 [Google Scholar]
  74. S. Giddings, A. Mills, J. Org. Chem., 1988, 53, 1103 [Google Scholar]
  75. G. Barak, Y. Sasson, J. Org. Chem., 1988, 53, 3553; [Google Scholar]
  76. J. Chem. Soc, Chem. Commun., 1987, 1266 [Google Scholar]
  77. B. M. Choudary, N. P. Reddy, M. L. Kantam, Z. Jamil, Tetrahedron Lett., 1985, 26, 6257 [Google Scholar]
  78. Y. Sasson, H. Wiener, S. Bashir, J. Chem. Soc, Chem. Commun., 1987, 1574 [Google Scholar]
  79. M. J. H. Russell, B. A. Murrer, European Appl. 61,337, 1982 [Google Scholar]
  80. Y. Dror, J. Manassen, J. Mol. Catal., 1977, 2, 219 [Google Scholar]
  81. K. R. Januszkiewicz, H. Alper, Organometallics, 1983, 2, 1055 [Google Scholar]
  82. J. Blum, I. Amer, A. Zoran, Y. Sasson, Tetrahedron Lett., 1983, 24, 4139 [Google Scholar]
  83. E. N. Marvell, T. Li, Synthesis, 1973, 457 [Google Scholar]
  84. J. Azran, O. Buchman, I. Amer, J. Blum, J. Mol. Catal., 1986, 34, 229 [Google Scholar]
  85. C. J. Longley, T. J. Goodwin, G. Wilkinson, Polyhedron, 1986, 5, 1625 [Google Scholar]
  86. R. Bar, Y. Sasson, Tetrahedron Lett., 1981, 22, 1709 [Google Scholar]
  87. R. Bar, Y. Sasson, J. Blum, J. Mol. Catal, 1984, 26, 327; [Google Scholar]
  88. R. Bar, L. K. Bar, Y. Sasson, J. Blum, J. Mol. Catal, 1985, 33, 161 [Google Scholar]
  89. A. Zoran, Y. Sasson, J. Mol. Catal, 1984, 27, 349 [Google Scholar]
  90. R. Bar, Y. Sasson, J. Blum, J. Mol. Catal, 1982, 16, 175 [Google Scholar]
  91. T. Okano, M. Iwahara, T. Suzuki, H. Konishi, J. Kiji, Chem. Lett. Jpn., 1986, 1467 [Google Scholar]
  92. H. Alper, S. Amaratunga, Tetrahedron Lett., 1980, 21, 2603 [Google Scholar]
  93. K. E. Hashem, J. F. Petrignani, H. Alper, J. Mol. Catal., 1984, 26, 285 [Google Scholar]
  94. K. Janusckiewicz, H. Alper, J. Mol. Catal., 1983, 19, 139 [Google Scholar]
  95. T. Okano, M. Yamamoto, T. Noguchi, H. Konishi, J. Kiji, Chem. Lett. Jpn., 1982, 977 [Google Scholar]
  96. H. Alper, K. Hachem, S. Gambarotta, Can. J. Chem., 1980, 58, 1599 [Google Scholar]
  97. N. M. Chistovalova, I. S. Akhrem, V. F. Sizoi, V. V. Bardin, M. E. Vol, lzv. Akad. Nauk SSSR, Ser. Khim., 1988, 1180 [Google Scholar]
  98. M. Miura, H. Hashimoto, K. Itoh, M. Nomura, Tetrahedron Lett., 1989, 30, 975 [Google Scholar]
  99. P. N. Rylander, “Catalytic Hydrogenation in Organic Syntheses”, Academic Press, Orlando, 1979 [Google Scholar]
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