Skip to content
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.

Loading

Article metrics loading...

/content/journals/10.1595/003214090X34129
1990-01-01
2024-06-25
Loading full text...

Full text loading...

/deliver/fulltext/pmr/34/1/pmr0034-0002.html?itemId=/content/journals/10.1595/003214090X34129&mimeType=html&fmt=ahah

References

  1. Schnell H. Angew. Chem., 1956, 68, 633 [Google Scholar]
  2. Starks C. M. Isr. J. Chem., 1985, 26, 211 [Google Scholar]
  3. Starks C. M., “Phase-Transfer Catalysis”, ed. and Starks C. M. 1985, 1 [Google Scholar]
  4. Dockx J. Synthesis, 1973, 441 [Google Scholar]
  5. Makosza M. Pure Appl. Chem., 1975, 43, 439 [Google Scholar]
  6. Brandstrom A. “Preparative Ion Pair Extraction”, Apotekarsocietet, Stockholm, 1976 [Google Scholar]
  7. Dehmlow E. V. Angew. Chem., Int. Ed. Engl., 1977, 16, 493 [Google Scholar]
  8. Weber W. P., and Gokel G. W. “Phase Transfer Catalysis in Organic Synthesis”, Springer Verlag, Berlin, 1977 [Google Scholar]
  9. Brandstrom A. Adv. Phys. Org. Chem., 1977, 15, 267 [Google Scholar]
  10. Makosza M. Russ. Chem. Rev., 1977, 46, 1151 [Google Scholar]
  11. Starks C. M., and Liotta C. “Phase Transfer Catalysis”, Academic Press, New York, 1978 [Google Scholar]
  12. Lehn J. M. Acc. Chem. Res., 1978, 11, 49 [Google Scholar]
  13. Mcintosh J. M. J. Chem. Ed., 1978, 55, 235 [Google Scholar]
  14. Gokel G. W., and Weber W. P. J. Chem. Ed., 1978, 55, 350 [Google Scholar]
  15. Weber W. P., and Gokel G. W. J. Chem. Ed., 1978, 55, 429 [Google Scholar]
  16. Makosza M. “ Survey of Progress in Chemistry”, Vol IX, Academic Press, New York, 1979 [Google Scholar]
  17. Keller W. E. “Compendium of Phase-Transfer Reactions and Related Synthetic Methods”, Fluka, Switzerland, 1979 [Google Scholar]
  18. Lindblom L., and Elander M. Pharm. Technol., 1980, (10), 59 [Google Scholar]
  19. Reuben B., and Sjoberg K. Chemtech, 1981, 315 [Google Scholar]
  20. Cocagne P., Elguero J., and Gallo R. Heterocycles, 1983, 20, 1379 [Google Scholar]
  21. Dehmlow E. V., and Dehmlow S. S. “Phase Transfer Catalysis”, Verlag Chemie, Weinheim, 1983 [Google Scholar]
  22. D’Incan E., Viout P., and Gallo R. Isr. J. Chem., 1985, 26, 277 [Google Scholar]
  23. Freedman H. H. Pure Appl. Chem., 1986, 58, 857 [Google Scholar]
  24. Cassar L. Ann. N.Y. Acad. Sci., 1980, 333, 208 [Google Scholar]
  25. Alper H. Adv. Organomet. Chem., 1981, 19, 183 [Google Scholar]
  26. Alper H. Fundam. Res. Homogeneous Catal., 1984, 4, 79 [Google Scholar]
  27. Des Abbaye H. Isr. J. Chem., 1985, 26, 249 [Google Scholar]
  28. Alper H. Prep. Am. Chem. Soc., Div. Pet. Chem., 1985, 30, 364 [Google Scholar]
  29. Alper H., “Phase-Transfer Catalysis”, ed. and Starks C. M. 1985, 8 [Google Scholar]
  30. Alper H., Hashem K., and Heveling J. Organometallics, 1982, 1, 775 [Google Scholar]
  31. Zhang S., Xiao S., Ran M., and Dai H. Fenzi Cuihua, 1987, 1, 115; CA 109:756531 [Google Scholar]
  32. Arzoumanian H., Buono G., Choukrad M’Barek, and Petrignani J. F. Organometallics, 1988, 7, 59 [Google Scholar]
  33. Galamb V., and Alper H. J. Chem. Soc., Chem. Commun., 1983, 88 [Google Scholar]
  34. Cassar L., Foa M., and Gardano A. J. Organomet. Chem., 1976, 121, C55 [Google Scholar]
  35. Galamb V., Gopal M., and Alper H. Organometallics, 1983, 2, 801 [Google Scholar]
  36. Galamb V., and Alper H. Transition Met. Chem., 1983, 8, 271 [Google Scholar]
  37. Choudary B. M., Reddy P. N., and Ashok B. Appl. Catal., 1987, 32, 357 [Google Scholar]
  38. Pri-Bar I., and Alper H. J. Org. Chem., 1989, 54, 36 [Google Scholar]
  39. Hallgren J. E., and Lucas G. M. J. Organomet. Chem., 1981, 212, 135 [Google Scholar]
  40. Hallgren J. E. U.S. Patent 4, 361, 519, 1980 [Google Scholar]
  41. Smith R. T., Unger R. K., Sanderson L. J., and Baird M. C. Ann. N.Y. Acad. Sci., 1983, 415, 253 [Google Scholar]
  42. Bahnnann H., Cornils B., Konkol W., and Lipps W. German Offen. 3,412, 335, 1985 [Google Scholar]
  43. Russell M. J. H. Platinum Metals Rev., 1988, 32, (4), 179 [Google Scholar]
  44. Kuntz E. G. Chemtech, 1987, 17, 570 [Google Scholar]
  45. Heck R. F. Org. React., 1982, 27, 345; [Google Scholar]
  46. “Palladium Reagents in Organic Synthesis”, Academic Press, London, 1985 [Google Scholar]
  47. Jeffery T. J. Chem. Soc, Chem. Commun., 1984, 1287 [Google Scholar]
  48. Jeffery T. Tetrahedron Lett., 1985, 26, 2667 [Google Scholar]
  49. Jeffery T. Synthesis, 1987, 70 [Google Scholar]
  50. Benhaddou R., Czernecki S., Ville G., and Zegar A. Organometallics, 1988, 7, 2435 [Google Scholar]
  51. Rossi R., Carpita A., Quirici M. G., and Gaudenzi M. L. Tetrahedron, 1982, 38, 631 [Google Scholar]
  52. Zahalka H. A., Januskiewicz K., and Alper H. J. Mol. Catal, 1986, 35, 249 [Google Scholar]
  53. Januskiewicz K., and Alper H. Tetrahedron Lett., 1983, 24, 5163 [Google Scholar]
  54. Gore E. S. Platinum Metals Rev., 1983, 27, (3), 111 [Google Scholar]
  55. Gore E. S., “Chemistry of the Platinum Group Metals: Recent Developments”, ed. by and Hartley F. R. Elsevier, Amsterdam, to be published [Google Scholar]
  56. Carlsen P. H. J., Katsuki T., Martin V. S., and Sharpless K. B. J. Org. Chem., 1981, 46, 3936 [Google Scholar]
  57. Januskiewicz K., and Alper H. Tetrahedron Lett., 1983, 24, 5159 [Google Scholar]
  58. Harada A., Hu Y., and Takahashi S. Chem. Lett. Jpn., 1986, 2083 [Google Scholar]
  59. Alper H., Januskiewicz K., and Smith D. J. H. Tetrahedron Lett., 1985, 26, 2263 [Google Scholar]
  60. Matsuda F., and Kato K. Japanese Appl. 61/68439, 1986 [Google Scholar]
  61. Kukes S. G., and Shioyama T. K. U.S. Patent 4,448, 892, 1984 [Google Scholar]
  62. Clement W. H., and Selwitz C. M. J. Org. Chem., 1964, 29, 241 [Google Scholar]
  63. Murtha T. P., and Shioyama T. K. U.S. Patent 4,434,082, 1984 [Google Scholar]
  64. Tsuji J. Org. Synth., 1984, 62, 9 [Google Scholar]
  65. Starks C. M., and Washecheck P. W. U.S. Patent 3,547,962, 1970 [Google Scholar]
  66. Foglia T. A., Barr P. A., and Malloy A. J. J. Am. OU Chem. Soc., 1977, 54, 858A [Google Scholar]
  67. Barak G., and Sasson Y. J. Chem. Soc, Chem. Commun., 1987, 1266 [Google Scholar]
  68. Dobson J. C., Seek W. K., and Meyer T. J. In-org. Chem., 1986, 25, 1514 [Google Scholar]
  69. Sasson Y., Zappi G. D., and Neumann R. J. Org. Chem., 1986, 51, 2880 [Google Scholar]
  70. Barak G., and Sasson Y. J. Chem. Soc, Chem. Commun., 1988, 637 [Google Scholar]
  71. Olson E. S., and Farnum B. W. Prep. Pap. ACS., Div. Fuel Chem., 1981, 26, 60 [Google Scholar]
  72. Morris P. E., and Kiely D. E. J. Org. Chem., 1987, 52, 1149 [Google Scholar]
  73. Yamamoto Y., Suzuki H., and Moro-oka Y. Tetrahedron Lett., 1985, 26, 2107 [Google Scholar]
  74. Giddings S., and Mills A. J. Org. Chem., 1988, 53, 1103 [Google Scholar]
  75. Barak G., and Sasson Y. J. Org. Chem., 1988, 53, 3553; [Google Scholar]
  76. J. Chem. Soc, Chem. Commun., 1987, 1266 [Google Scholar]
  77. Choudary B. M., Reddy N. P., Kantam M. L., and Jamil Z. Tetrahedron Lett., 1985, 26, 6257 [Google Scholar]
  78. Sasson Y., Wiener H., and Bashir S. J. Chem. Soc, Chem. Commun., 1987, 1574 [Google Scholar]
  79. Russell M. J. H., and Murrer B. A. European Appl. 61,337, 1982 [Google Scholar]
  80. Dror Y., and Manassen J. J. Mol. Catal., 1977, 2, 219 [Google Scholar]
  81. Januszkiewicz K. R., and Alper H. Organometallics, 1983, 2, 1055 [Google Scholar]
  82. Blum J., Amer I., Zoran A., and Sasson Y. Tetrahedron Lett., 1983, 24, 4139 [Google Scholar]
  83. Marvell E. N., and Li T. Synthesis, 1973, 457 [Google Scholar]
  84. Azran J., Buchman O., Amer I., and Blum J. J. Mol. Catal., 1986, 34, 229 [Google Scholar]
  85. Longley C. J., Goodwin T. J., and Wilkinson G. Polyhedron, 1986, 5, 1625 [Google Scholar]
  86. Bar R., and Sasson Y. Tetrahedron Lett., 1981, 22, 1709 [Google Scholar]
  87. Bar R., Sasson Y., and Blum J. J. Mol. Catal, 1984, 26, 327; [Google Scholar]
  88. Bar R., Bar L. K., Sasson Y., and Blum J. J. Mol. Catal, 1985, 33, 161 [Google Scholar]
  89. Zoran A., and Sasson Y. J. Mol. Catal, 1984, 27, 349 [Google Scholar]
  90. Bar R., Sasson Y., and Blum J. J. Mol. Catal, 1982, 16, 175 [Google Scholar]
  91. Okano T., Iwahara M., Suzuki T., Konishi H., and Kiji J. Chem. Lett. Jpn., 1986, 1467 [Google Scholar]
  92. Alper H., and Amaratunga S. Tetrahedron Lett., 1980, 21, 2603 [Google Scholar]
  93. Hashem K. E., Petrignani J. F., and Alper H. J. Mol. Catal., 1984, 26, 285 [Google Scholar]
  94. Janusckiewicz K., and Alper H. J. Mol. Catal., 1983, 19, 139 [Google Scholar]
  95. Okano T., Yamamoto M., Noguchi T., Konishi H., and Kiji J. Chem. Lett. Jpn., 1982, 977 [Google Scholar]
  96. Alper H., Hachem K., and Gambarotta S. Can. J. Chem., 1980, 58, 1599 [Google Scholar]
  97. Chistovalova N. M., Akhrem I. S., Sizoi V. F., Bardin V. V., and Vol M. E. lzv. Akad. Nauk SSSR, Ser. Khim., 1988, 1180 [Google Scholar]
  98. Miura M., Hashimoto H., Itoh K., and Nomura M. Tetrahedron Lett., 1989, 30, 975 [Google Scholar]
  99. Rylander P. N. “Catalytic Hydrogenation in Organic Syntheses”, Academic Press, Orlando, 1979 [Google Scholar]
/content/journals/10.1595/003214090X34129
Loading
/content/journals/10.1595/003214090X34129
Loading

Data & Media loading...

  • Article Type: Research Article
This is a required field
Please enter a valid email address
Approval was a Success
Invalid data
An Error Occurred
Approval was partially successful, following selected items could not be processed due to error