Skip to main content
Log in

Heteropoly acids, their salts and polyoxometalates as heterogenous, efficient and eco-friendly catalysts in organic reactions: Some recent advances

  • Review
  • Published:
Journal of the Iranian Chemical Society Aims and scope Submit manuscript

Abstract

In this review article, some recent advances of applying heteropoly acids and polyoxometalates as heterogeneous, reusable and eco-friendly catalysts in organic synthesis are discussed.

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

Access this article

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. P.T. Anastas, J.C. Warner, Green Chemistry, Theory and Practice, Oxford University Press, 1998

  2. J.H. Clark, Green Chemistry 1 (1999) 1.

    CAS  Google Scholar 

  3. V. Kozhevnikov, in: E. Derouane (Ed.), Catalysts for Fine Chemical Synthesis, Catalysis by Polyoxometalates 2, Wiley, New York, 2002.

    Google Scholar 

  4. S. Nakato, M. Kimura, T. Okuhara, Chem. Lett. (1997) 389.

  5. M. Kimura, T. Nakato, T. Okuhara, Appl. Catal. A Gen. 165 (1997) 227.

    CAS  Google Scholar 

  6. T. Nakato, Kimura, M. Nakata, S. Okuhara, T. Langmuir 14 (1998) 319.

    Google Scholar 

  7. REF

  8. J.H. Clark, Chem. Rev. 80 (1980) 429.

    CAS  Google Scholar 

  9. R.A. Sheldon, Chirotechnologies, Industrial Synthesis of Optically Active Compounds; Dekker Publishing: New York, 1993.

    Google Scholar 

  10. E. Emori, T.H. Sasai, M. Shibasaki, J. Am. Chem. Soc. 120 (1998) 4043.

    CAS  Google Scholar 

  11. S. Kanemasa, Y. Oderaotoshi, E. Wada, J. Am. Chem. Soc. 121 (1999) 8675

    Google Scholar 

  12. M. Bandini, P.G. Cozzi, M. Giacomini, P. Melchiorre, S. Selva, A. Umani-Ronchi, J. Org. Chem. 67 (2002) 3700

    CAS  Google Scholar 

  13. N. Srivastava, K. Banic, J. Org. Chem. 68 (2003) 2109

    CAS  Google Scholar 

  14. K. Subbareddy, A. Sudalai, B.C. Benicewicz, Tetrahedron Lett. 42 (2001) 3791

    Google Scholar 

  15. J.S. Yadav, B.V.S. Reddy, G. Baishya, J. Org. Chem. 68 (2003) 7098

    CAS  Google Scholar 

  16. B.C. Ranu, S.S. Dey, A. Hajra, Tetrahedron 59 (2003) 2417

    CAS  Google Scholar 

  17. T.C. Wabnitz, J.B. Spencer, Org. Lett. 5 (2003) 2141

    CAS  Google Scholar 

  18. T.C. Wabnitz, J. Yu, J.B. Spencer, Synlett (2003) 1070.

    Google Scholar 

  19. H. Firouzabadi, N. Iranpoor, A.A. Jafari, Synlett (2005) 299.

  20. H. Heaney, in: B.M. Trost, I. Fleming (Eds.), Comprehensive Organic Synthesis Pergamon Press, Oxford, 1991, pp. 733-752.

  21. T. Harada, T. Ohno, S. Kobayashi, T. Mukaiyama, Synthesis (1991) 1216

  22. A. Kawada, S. Mitamura, S. Kobayashi, Synlett (1994) 545

  23. S. Pivsa-Art, K. Okura, M. Miura, S. Murata, M. Nomura, J. Chem. Soc. PerkinTrans1 13 (1994) 1703

    Google Scholar 

  24. A. Kawada, S. Mitamura, S. Kobayashi, J. Chem. Soc. Chem. Commun. (1996) 183

  25. F. Effenberger, J.K. Eberhard, A.H. Maier, J. Am. Chem. Soc. 118 (1996) 12572

    CAS  Google Scholar 

  26. J.Nishikido, H. Nakajima, T. Saeki, A. Ishii, K. Mikami, Synlett (1998) 1347

  27. S. Repichet, C.L. Roux, J. Dubac, J.R. Desmurs, Eur. J. Org. Chem. (1998) 2743

  28. H. Nakano, T. Kitazume, Green Chem. (1999) 179

  29. J. Matsuo, K. Odashima, S. Kobayashi, Synlett (2000) 403.

  30. A.G.M. Barrett, N. Bouloc, D.C. Braddock, D. Chadwick, D.A. Hendersona, Synlett (2002) 1653

  31. G. Bartoli, M. Bosco, E. Marcantoni, M. Massaccesi, S. Rinaldi, Sambri, L. Tetrahedron Lett.43 (2002) 6331.

    CAS  Google Scholar 

  32. Q.L. Wang, Y. Ma, X. Ji, H. Yan, Q. Qiu, J. Chem. Soc. Chem. Commun. (1995) 2307

  33. J. Kaur, I.V. Kozhevnikov, Chem. Commun. (2002) 2508

  34. B. Chiche, A. Finiels, C. Gauthier, P. Geneste, J. Org. Chem. 51 (1986) 2128

    CAS  Google Scholar 

  35. B.C. Ranu, K. Ghosh, U. Jana, J. Org. Chem. 61 (1996) 9546.

    CAS  Google Scholar 

  36. H. Firouzabadi, N. Iranpoor, F. Nowrouzi, Tetrahedron 60 (2004) 10843

    CAS  Google Scholar 

  37. H. Firouzabadi, N. Iranpoor, F. Nowrouzi, Tetrahedron Lett. 44 (2003) 5343.

    CAS  Google Scholar 

  38. W.R. Jackson, H.A. Jacobs, B.R. Matthews, G.S. Jayatilake, K.G. Watson, Tetrahedron Lett. 31 (1990) 1447

    CAS  Google Scholar 

  39. T. Ziegler, B. Horsch, F. Effenberger, Synthesis (1990) 575

  40. P. Zandbergen, J. Brussee, A. Van der Gen, C.G. Kruse, Tetrahedron Asymmetry 3 (1992) 769.

    CAS  Google Scholar 

  41. R.J.H. Gregory, Chem. Rev. 99 (1999) 3649

    CAS  Google Scholar 

  42. H. Deng, M.P. Ister, M.L. Snapper, A.H. Hoveyda, Angew. Chem. Int. Ed. 41 (2002) 1009

    CAS  Google Scholar 

  43. S.K. Tian, R. Hong, L. Deng, J. Am. Chem. Soc. 125 (2003) 9900

    CAS  Google Scholar 

  44. N. Azizi, M.R. Saidi, J. Organometallic Chem. 688 (2003) 283

    CAS  Google Scholar 

  45. Z. Wang, B. Fetterly,J.G. Verkade J. Organometallic Chem. 646 (2002) 161.

    CAS  Google Scholar 

  46. M. Bandini, P.G. Cozzi, P. Melchiorre, A.V. Ronchi, Tetrahedron Lett. 42 (2001) 3041

    CAS  Google Scholar 

  47. M. Curini, F. Epifano, M.C. Marcotullio, O. Rosati, M. Rossi, Synlett (2002) 315

  48. F.Chen, X. Feng, B. Qin, G. Zhang, Y. Jiang, Synlett (2003) 558

  49. Y. Shen, X. Feng, Y. Li, G. Zhang, Y. Jiang, Tetrahedron 59 (2003) 5667

    CAS  Google Scholar 

  50. Y. Shen, X. Feng, Y. Li, G. Zhang, Y. Jiang, Synlett (2002) 793

  51. S.S. Kim, D.W. Kim, G. Rajagopal, Synthesis 2 (2004) 213

    Google Scholar 

  52. H.S. Wilkinson, P.T. Grover, C.P. Vandenbossche, R.P. Bakale, N.N. Bhongle, S.A. Wald, C.H. Senanayake, Org. Lett. 3 (2001) 553.

    CAS  Google Scholar 

  53. H. Firouzabadi, N. Iranpoor, A.A. Jafari, J. Organometallic Chem. 690 (2005) 1556.

    CAS  Google Scholar 

  54. N. Bagget, In Comprehensive Organic Synthesis; series Ed. by D. Barton, W.D. Ollis, vol. Ed. Stoddart J. F.; Pergaman, Oxford, 1979, P. 799.

  55. M.B. Smith, J. March, Advanced Organic Chemistry, 5th Edition, Wiley-Interscience, New York, 2001, pp. 479-480.

    Google Scholar 

  56. T. Ooi, H. Ichikawa, Y. Itagaki, K. Maruoka, Heterocycles 52 (2000) 575

    CAS  Google Scholar 

  57. K. Manab, S. Limura, X. Sun, S. Kobayashi J. Am. Chem. Soc. 124 (2002) 11971.

    Google Scholar 

  58. N. Iranpoor, E. Mottaghinejad, Synth. Commun. 25 (1995) 2253

    CAS  Google Scholar 

  59. P. Salehi, N. Iranpoor, F. Kargar Behbahani, Tetrahedron 54 (1998) 943.

    CAS  Google Scholar 

  60. J.S. Bajwa, X. Jiang, J. Slade, K. Prasad, O. Repic, T. J. Blacklock, Tetrahedron Lett. 43 (2002) 6709

    CAS  Google Scholar 

  61. X. Jiang, J.S. Bajwa, J. Slade, K. Prasad, O. Repic, T.J. Blacklock, Tetrahedron Lett.43 (2002) 9225.

    CAS  Google Scholar 

  62. H. Firouzabadi, N. Iranpoor, A.A. Jafari, J. Molecular Cat. A Chemical 227 (2005) 97.

    CAS  Google Scholar 

  63. S.G. Wilkinson, in: J.F. Stoddart (Ed.), In Comprehensive Organic Chemistry, Vol. 1; Pergamon Press: Oxford, 1979, Chap 4.1, 579–706

    Google Scholar 

  64. T.W. Green, P.G.M. Wuts, In Protective Groups in Organic Synthesis, 3rd Ed.; John Wiley & Sons: New York, 1999.

    Book  Google Scholar 

  65. H. Firouzabadi, N. Iranpoor, A.A. Jafari, Tetrahedron Lett. 46 (2005) 2683.

    CAS  Google Scholar 

  66. A.B. Smith, S.M. Condon, J.A. McCauley, Acc. Chem. Res. 31 (1998) 35.

    CAS  Google Scholar 

  67. P.C. Bulman Page, J.C. Prodger, D. Westwood, Tetrahedron 49 (1993) 10355.

    CAS  Google Scholar 

  68. J. Taleiwa, H. Horiuchi, S. Vemura, J. Org. Chem. 60 (1995) 4039.

    Google Scholar 

  69. S. Muthusamy, S.A. Babu, C. Gunanathan, Tetrahedron Lett. 42 (2001) 359

    CAS  Google Scholar 

  70. L.F. Tietze, B. Weigand, C. Wulff, Synthesis (2000) 69.

  71. H. Firouzabadi, N. Iranpoor, B. Karimi, H. Hazarkhani, Synlett (2000) 263

  72. H. Firouzabadi, N. Iranpoor, B. Karimi, Synlett (1999) 319

  73. H. Firouzabadi, N. Iranpoor, B. Karimi, Synthesis (1999) 58.

  74. R. Vijaya Anand, P. Saravanan, V.K. Singh, Synlett (1999) 415.

  75. F. Bellesia, M. Boni, F. Ghelf, U.M. Pagnoni, Tetrahedron 49 (1993) 199

    CAS  Google Scholar 

  76. G.K. Jnaneshwara, N.B. Barhate, A. Sudalai, V.H. Deshpande, A.S. Gajare, M.S. Shingare, R. Sukumar, J. Chem. Soc. Perkin Trans. 1 (1998) 965.

    Google Scholar 

  77. H. Firouzabadi, N. Iranpoor, K. Amani, Synthesis (2002) 59.

  78. C.A Bruynes, T.K. Jurriens, J. Org. Chem. 47 (1982) 3966.

    Google Scholar 

  79. K. Tanaka, F. Toda, Chem. Rev. 100 (2000)1025

    CAS  Google Scholar 

  80. H. Firouzabadi, N. Iranpoor, S. Sobhani, Tetrahedron Lett. 43 (2002) 3653

    CAS  Google Scholar 

  81. H. Firouzabadi B. Karimi, Synth. Commun. 23 (1993) 1633

    CAS  Google Scholar 

  82. H. Firouzabadi, A. R. Sardarian, Z. Khayat, B. Karimi S. Tangestaninejad, Synth. Commun. 27 (1997) 2709

    CAS  Google Scholar 

  83. B. Karimi, B. Golshani, J. Org. Chem. 65 (2000) 7228.

    CAS  Google Scholar 

  84. H. Firouzabadi, N. Iranpoor, K.Amani, F. Nowrouzi, J. Chem. Soc. Perkin Trans. 1 (2002) 2601.

    Google Scholar 

  85. M.H. Habibi, S. Tangestaninejad, I. Mohammadpoor-Baltork, V. Mirkhani, B. Yadollahi Tetrahedron Lett. 42 (2001) 6771.

    CAS  Google Scholar 

  86. W. Steglich, G. Höfle, Angew. Chem. Int. Ed. Engl., 8 (1969) 981

    CAS  Google Scholar 

  87. G. Höfle, W. Steglich, H. Vorbrüggen, Angew. Chem. Int. Ed. Engl.17 (1978) 569.

    Google Scholar 

  88. K.K. Chauhan, C.G. Frost, L. Love, D. Waite, Synlett (1999) 1743

  89. K. Ishihara, M. Kubota, H. Kurihara H. Yamamoto, J. Org. Chem. 61 (1996) 4560

    CAS  Google Scholar 

  90. A. Orita, C. Tanahashi, A. Kakuda, J. Otera Angew. Chem. Int. Ed., 39 (2000) 2877

    CAS  Google Scholar 

  91. M.D. Carrigan, D. A. Freiberg, R.C. Smith, H.M. Zerth R.S. Mohan, Synthesis (2001) 2091.

  92. H. Firouzabadi, N. Iranpoor, F. Nowrouzi, K. Amani, Chem. Commun. (2003) 764.

  93. M.H. Habibi, S. Tangestaninejad, V. Mirkhani, B. Yadollahi Monatshefte Fur Chemie 133 (2002) 323

    CAS  Google Scholar 

  94. M.H. Habibi, S. Tangestaninejad, V. Mirkhani, B. Yadollahi Tetrahedron 57 (2001) 8333.

    CAS  Google Scholar 

  95. K.S. Kochhar, B.S. Bal, R.P. Deshpande, S.N. Rajadhyaksha, H.W. Pinnick, J. Org. Chem. 48 (1983) 1765.

    CAS  Google Scholar 

  96. B.M. Trost, C.B. Lee, J.M. Weiss, J. Am. Chem. Soc. 117 (1995) 7247

    CAS  Google Scholar 

  97. N. Deka, D.J. Kalita, R. Borah, J. C. Sharma, J. Org. Chem. 62 (1997) 1563

    CAS  Google Scholar 

  98. K.L. Chandra, P. Saravanan, V.K. Singh, Synlett (2000) 359

  99. B. Karimi, H. Seradj, G.R. Ebrahimian, Synlett (2000) 623

  100. N. Sumida, K. Nishioka, T. Sato, Synlett (2001) 1921

  101. B.M. Trost, C.B. Lee, J. Am. Chem. Soc.123 (2001) 3671

    CAS  Google Scholar 

  102. S.C. Roy, B. Banerjee, Synlett (2002) 1677.

  103. a) Sandberg, M. Sydnes, L.K. Tetrahedron Lett. 39 (1998) 6361

    Google Scholar 

  104. M. Sandberg, L.K. Sydnes, Org. Lett. 2 (2000) 687.

    CAS  Google Scholar 

  105. H. Firouzabadi, N. Iranpoor, F. Nowrouzi, K. Amani Tetrahedron Lett. 44 (2003) 3951.

    CAS  Google Scholar 

  106. S.M. Dirk, E.T. Mickelson, J.C. Henderson, J.M. Tour, Org. Lett. 2 (2000) 3405.

    CAS  Google Scholar 

  107. K.S. Webb, V. Seneviratne, Tetrahedron Lett. 36 (1995) 2377

    CAS  Google Scholar 

  108. S. Tollari, D. Vergani, S. Banfi, F. Porta, J. Chem. Soc. Chem. Commun. (1993) 442

  109. S. Sakaue, T. Tsubakino, Y. Nishiyama, Y. Ishii, J. Org. Chem. 58 (1993) 3633.

    CAS  Google Scholar 

  110. Z. Zhu, J.H. Espenson, J. Org. Chem. 60 (1995) 1326

    CAS  Google Scholar 

  111. S. Sakaue, T. Tsubakino, Y. Nishiyama, Y. Ishii, J. Org. Chem. 58 (1993) 3633.

    CAS  Google Scholar 

  112. J. Muzart, Synthesis (1995) 1325.

  113. H. Firouzabadi, N. Iranpoor, F. Nowrouzi, K. Amani, Green Chem. 3 (2001) 131.

    CAS  Google Scholar 

  114. N.D. Cheronis, J.B. Entrikin, Identification of Carbonyl Compounds, Interscience: New York, 1963.

  115. H.M.S. Kumar, T.P. Reddy, J.S. Yadav, Synthesis (1999) 586.

  116. P.R. Dave, F. Forshar, J. Org. Chem. 61 (1996) 8897.

    CAS  Google Scholar 

  117. M.E. Enikaki, X.N. Stamplos, T.A. Charalambis, C.C. Karapostolon, Tetrahedron 53 (1997) 747.

    Google Scholar 

  118. S. Negi, M. Matsukura, M. Mizuno, K. Miyake, Synthesis (1996) 991.

  119. J.T. Pulkkiner. J.J. Vepsalainen, J. Org. Chem. 61 (1996) 8604.

    Google Scholar 

  120. J.K. Whitesell, M.A. Whitesell, Synthesis (1983) 54.

  121. W. Chrisman, M.J. Blankinship, B. Taylor, C.E. Harris, Tetrahedron Lett. 42 (2001) 4775

    CAS  Google Scholar 

  122. A.R. Hajipour, N. Mahboubhgah, Org. Prep. Proced. Int. 31 (1999) 112.

    CAS  Google Scholar 

  123. A. Corsaro, U. Chiacchio, V. Pistara, Synthesis (2001) 1903.

  124. J.G. Lee, J.P. Hwang, Chem. Lett. 7 (1995) 507.

    Google Scholar 

  125. H.M. Meshram, G.S. Reddy, D. Srinivas, J.S. Yadav, Synth. Commun. 28 (1998) 2593.

    CAS  Google Scholar 

  126. B.A. Nattier, K.J. Eash, R.S. Mohan, Synthesis (2001) 1010

  127. B. Tamami, A. Kiasat, Synth. Commun. 30 (2000) 4129

    CAS  Google Scholar 

  128. A. McKillop, J.D. Hunt, E.C. Taylor, R.D. Naylor J. Am. Chem. Soc. 93 (1971) 4918

    Google Scholar 

  129. J.W. Bird, D.G.M. Diaper, Can. J. Chem. 47 (1969) 145.

    CAS  Google Scholar 

  130. H. Firouzabadi, N. Iranpoor, K. Amani, Synthetic Commun. 34 (2004) 3587.

    CAS  Google Scholar 

  131. N.R. Williams, J.D. Wander The Carbohydrates Chemistry and Biochemistry; Academic: New York, 1980, p. 761.

    Google Scholar 

  132. J. Ramnauth, O. Poulin, S.P. Rakhit, S.P. Maddaford, Org. Lett. 3 (2001) 2013.

    CAS  Google Scholar 

  133. P. Collins, R. Ferrier, Monosaccharides: their Chemistry and their Roles in Natural Products; Wiley: Chichester (1995).

    Google Scholar 

  134. K. Toshima, K. Tatsuta, Chem. Rev. 93 (1993) 1503

    CAS  Google Scholar 

  135. D.E. Levy, C. Tang, The Chemistry of C-Glycosides; Pergamon: New York, 1995.

    Google Scholar 

  136. P. KlaOke, D. Springer, J. Thiem, Liebigs Ann Chem. (1991) 509.

  137. P. Bhate, D. Horton, W. Priebe, Carbohydr. Res. 144 (1985) 331.

    CAS  Google Scholar 

  138. G. Matsuo, M. Kakata, S. Matsumura, Chem. Commun. (1996) 1379.

  139. K. Toshima, T. Ishizuka, G. Matsuo, M. Nakata, M. Konoshita J. Chem. Soc. Chem. Commun. (1993) 704.

  140. N.R. Swamy, Y. Venkateswarlu, Synthesis 5 (2002) 598.

    Google Scholar 

  141. B. Fraser-Reid, R.J. Madsen, Org. Chem. 60 (1995) 3851.

    Google Scholar 

  142. J.C. Lopez, B. Fraser-Reid, J. Chem. Soc. Chem. Commun. (1992) 94.

  143. B.B. Babu, K.K. Balasubramanian, Tetrahedron Lett. 41 (2000) 1271.

    CAS  Google Scholar 

  144. R.R. Schmidt, Angew. Chem. Int. Ed. Engl. 25 (1986) 212

    Google Scholar 

  145. G.J. Boons Tetrahedron 52 (1996) 1095.

    CAS  Google Scholar 

  146. E. Rafiee, S. Tangestaninejad, M.H. Habibi, V. Mikhani Bioorg. Med. Chem. Lett. 14 (2004) 3611.

    CAS  Google Scholar 

  147. C.N. Smith, D. Burnett, J. Econ. Entomol 42 (1949) 439.

    CAS  Google Scholar 

  148. Piper, Hall, Wright, Ind. Eng. Chem. 43 (1951) 11.

    Google Scholar 

  149. S.G. Cohen, R.M. Schultz, S.Y. Weinstein, J. Am. Chem. Soc. 88 (1966) 5315.

    CAS  Google Scholar 

  150. P. Huszthy, J.S. Bradshaw, C.Y. Zhu, R.M. Izatt, J. Org. Chem. 56 (1991) 3330

    CAS  Google Scholar 

  151. T. S. Jin, R.Y. Ma, Y. Li, X. Sun, T.S. Li, Synthetic Commun. 31 (2001) 2051.

    CAS  Google Scholar 

  152. E. Rafiee, S. Tangestaninejad, M.H. Habibi, V. Mikhani, Bull. Korean Chem. Soc. 25 (2000) 599.

    Google Scholar 

  153. E.J. Corey, H. Niwa, J. Knolle, J. Am. Chem. Soc. 100 (1978) 1942.

    CAS  Google Scholar 

  154. S. Kim, J.H. Park, Tetrahedron Lett. 28 (1987) 439

    CAS  Google Scholar 

  155. G.A. Olah, A. Husain, B.P. Singh, Synthesis (1983) 892

  156. R. Cruz-Almanza, F.J. Perez-Felores, M. Avila, Synthetic Commun. 20 (1990) 1125

    CAS  Google Scholar 

  157. J. Otera, Y. Niibo, S. Chikada, H. Nozaki, Synthesis (1988) 328

  158. A. Wagner, M.P. Heitz, C. Mioskovski, J. Chem. Soc. Chem. Commun. (1989) 1619

  159. S. Raina, V.K. Singh, Synthetic Commun. 25 (1995) 2395.

    CAS  Google Scholar 

  160. M.H. Habibi, S. Tangestaninejad, I. Mohammadpoor-Baltork, V. Mirkhani, B. Yadollahi, Tetrahedron Lett. 42 (2001) 2851.

    CAS  Google Scholar 

  161. G.A. Roger, S.M. Parsons, D.C. Anderson, L.M. Nilsson, B.A. Bahr, W.D. Kornreieh, R. Kaufman, R.S. Jacobs, B. Kirtman, J. Med. Chem.32 (1989) 1217.

    Google Scholar 

  162. S. Sagava, H. Abe, Y.T. Hase, Inabe, J. Org. Chem. 64 (1999) 4962

    Google Scholar 

  163. G. Sekar, V.K. Sing, J. Org. Chem. 64 (1999) 287

    CAS  Google Scholar 

  164. J. Auge, F. Leroy, Tetrahedron Lett. 37 (1996) 7715

    CAS  Google Scholar 

  165. M. Meguro, N. Asao, Y. Yamamoto, J. Chem. Soc. Prkin Trans I (1994) 2597

    Google Scholar 

  166. S. Rampalli. S.S. Chaudhari. K.G. Akamanchi, Synthesis 1 (2000) 8

    Google Scholar 

  167. S. Chandrasekhar, T. Ramachandar, S.J. Prakash, Synthesis (2000) 1817

  168. L.R. Reddy, M.A. Reddy, N. Bhanumathi, K.R. Rao, Synthesis (2001) 831.

  169. E. Rafiee, S. Tangestaninejad, M.H. Habibi, V. Mikhani, Synthetic Commun. 34 (2004) 3673.

    CAS  Google Scholar 

  170. D.M. Clod, Chem. Rev. 79 (1979) 491

    Google Scholar 

  171. J.J. Brown, R.H. Lenhard, S. Brestein, J. Am. Chem. Soc.86 (1964) 2183

    CAS  Google Scholar 

  172. R.P. Hanzlik, Leinwetter, J. Org. Chem. 43 (1978) 438

    CAS  Google Scholar 

  173. J. Wolinski, A. Czerwinska, Acta Pol. Pharm. 33 (1976) 696

    CAS  Google Scholar 

  174. K. Bruns, J. Conrad, A. Steigel, Tetrahedron 35 (1979) 4543

    Google Scholar 

  175. F.A. Meskens, Synthesis (1981) 501.

  176. L.W. Zatorski, P.T. Wiezchowski, Catal. Lett.10 (1991) 211

    Google Scholar 

  177. N. Iranpoor, B. Zeynizadeh, J. Chem. Res. (S) (1998) 466

  178. N. Iranpoor, F. Kazemi, Synthetic Commun. 28 (1998) 3189

    CAS  Google Scholar 

  179. I. Mohammadpoor-Baltork, H. Alian, A.R. Khosropour, Synthetic Commun. 31 (2001) 3411

    CAS  Google Scholar 

  180. N. Iranpoor, H. Adibi, Bull. Chem. Soc. Jpn. 73 (2000) 675.

    CAS  Google Scholar 

  181. a) Kagan, B.E. Firth, N.Y. Shih, C. Boyajian, J. Org. Chem. 42 (1977) 343

    CAS  Google Scholar 

  182. D.J. Harvey, Res. Commun. Chem. Pathol. Pharmacol. 4 (1972) 247

    CAS  Google Scholar 

  183. D.S. Torok, J.J. Figueroa, W.J. Scott, J. Org. Chem. 58 (1993) 7274.

    CAS  Google Scholar 

  184. V. Mirkhani, S. Tangestaninejad, B. Yadollahi, L. Alipanah, Catalysis Lett. 91 (2003) 129.

    CAS  Google Scholar 

  185. B. Meunier, Chem. Rev. 92 (1992) 1411.

    CAS  Google Scholar 

  186. Y. Ishii, M. Ogawa, Hydrogn Peroxide Catalyzed by Heteropoly Acids Combined with Cetylpyridinium Chloride, MYU, Tokyo, 1990.

  187. A. J. Bailey, W. P. Griffith, B. C. Parkin, J. Chem. Soc. Dalton Trans. (1995) 1833.

  188. R. Neumann, M. Gara, J. Am. Chem. Soc. 116 (1994) 5509.

    CAS  Google Scholar 

  189. S. Tangestaninejad, B. Yadollahi, Chemistry Lett. (1998) 511.

  190. Comprehensive Organic Synthesis (Oxidation); in: B.M. Trost (Ed.), Pergamon; New York, 1991, vol. 7.

  191. J. Muzart, Chem. Rev. 92 (1992) 113.

    CAS  Google Scholar 

  192. P. Laszlo, A. Cornelis, Synthesis (1985) 909

  193. B. Khadilkar, S. Borkar, Synthetic Commun. 28 (1998) 207

    CAS  Google Scholar 

  194. M. Hirano, K. Komiya, T. Morimito, Org. Prep. Proced. Int. 27 (1995) 703.

    CAS  Google Scholar 

  195. M.M. Heravi, D. Ajami, M.M. Mojtahedi, M. Ghassemzadeh, Chem. Commun. ( 1999 ) 833.

  196. H. Firouzabadi, N. Iranpoor, K. Amani, Synthesis (2003) 408.

  197. C. Christophersen, Acta. Chemica. Scand. 39B (1985) 515

    Google Scholar 

  198. A. Butler, J.V. Walker, Chem. Rev. 93 (1993) 1937.

    CAS  Google Scholar 

  199. H.A. Muathen, J. Org. Chem. 57 (1992) 2740.

    CAS  Google Scholar 

  200. K. Smith, G.A. El-Hiti, M. E.W. Hammond, D. Bahzad, Z. Li, C. Siquet, J. Chem. Soc. Perkin Trans. 1 (2000) 2745

    Google Scholar 

  201. J.H. Clark, J.C. Ross, D.J. Macquarrie, S.J. Barlow, T.W. Bastock, (1997) 1203

  202. T.J. Oberhauser, Org. Chem. 62 (1997) 4504.

    CAS  Google Scholar 

  203. H. Firouzabadi, N. Iranpoor, K. Amani, J. Mol. Cat. A Chemical195 (2003) 289.

    CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to H. Firouzabadi.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Firouzabadi, H., Jafari, A.A. Heteropoly acids, their salts and polyoxometalates as heterogenous, efficient and eco-friendly catalysts in organic reactions: Some recent advances. JICS 2, 85–114 (2005). https://doi.org/10.1007/BF03247201

Download citation

  • Received:

  • Accepted:

  • Issue Date:

  • DOI: https://doi.org/10.1007/BF03247201

Keyword

Navigation