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Some applications of zirconium(IV) tetrachloride (ZrCl4) and zirconium(IV) oxydichloride octahydrate (ZrOCl2.8H2O) as catalysts or reagents in organic synthesis

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An Erratum to this article was published on 01 September 2008

Abstract

Both ZrCl4 and ZrOCl2.8H2O are commercially available solid chemicals. Due to their low toxicities (LD50 [ZrCl4 oral rate] = 1688 mg/kg), (LD50 [ZrOCl2.8H2O oral rate] = 2950 mg/kg), low costs, ease of handling, high activity, the zirconium(IV) compounds are potential green catalysts or reagents which are of importance from different views. In this review we have paid attention to the applications of these compounds as reagents or catalysts in Friedel-Crafts reactions, Fries rearrangements, reduction and oxidation reactions, cycloaddition and hydrometalation reactions, protection and deprotection of functional groups, reactions of epoxides, iodination of alcohols, S-alkylation of thiols with alcohols, Michael addition, condensation of indoles with carbonyl compounds, Claisen ester condensation, Baylis-Hillman reaction, preparation of organozirconium compounds and some other miscellaneous reactions.

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References

  1. B.M. Trost, in: M. Beller, C. Bolm (Ed.), Transition Metal Organic Reactions, WILEY-VCH Verlag GmbH, D-69469, Weinheim, Germany, 1998.

  2. J.P. Riley, R. Chester, Introduction to Marine Chemistry, Academic Press, New York, 1971.

  3. R.J.S.R.Lewis, Dangerous Properties of Industrial Materials, Van Nostrand Reinhold, 8th ed., Vol. 3, New York, 1989.

  4. S. Pivsa-Art, K. Okuro, M. Miura, S. Murata, M. Nomura, J. Chem. Soc., Perkin Trans 1 (1994) 1703

    Google Scholar 

  5. Hein, D.L. Cottle, H.L. Van Matter, J. Am. Chem. Soc. 68 (1946) 524

    Google Scholar 

  6. P.H. Gore, J. A. Hoskins,J. Chem. Soc. (1964) 5666.

    Google Scholar 

  7. M. Segi, T. Nakajima, S. Suga, Bull. Chem. Soc. Jpn. 53 (1980) 1465.

    CAS  Google Scholar 

  8. D.C. Harrowven, R.E. Dainty, Tetrahedron Lett. 37 (1996) 3607.

    CAS  Google Scholar 

  9. D.C. Harrowven, R.F. Dainty, Tetrahedron Lett. 37 (1996) 7659.

    CAS  Google Scholar 

  10. K. Purushothama Chary, R.M. Thomas, D.S. Iyengar, Indian J. Chem. 39B (2000) 57.

    Google Scholar 

  11. S. Itsuno, Y. Sakurai, K. Ito, Synthesis (1988) 995.

  12. S. Itsuno, Y. Sakurai, K. Shimizu, K. Ito, J. Chem. Soc. Perkin Trans 1 (1990) 1859.

    Google Scholar 

  13. K. Purushothama Chary, G.H. Mohan, D.S. Iyengar, Chem. Lett. (1999) 1339.

  14. K. Purushothama Chary, S. Raya Ram, D.S. Iyengar, Synlett (2000) 683.

  15. H. Firouzabadi, N. Iranpoor, M. Jafarpour, J. Sulfur Chem. 26 (2005) 313.

    CAS  Google Scholar 

  16. G.J. Hollingworth, in: R. Katritzky, A.O. Meth-Cohn, C.W. Rees, G. Pattenden (Eds.), In Comprehensive Organic Functional Group Transformations, Elsevier: Oxford, Vol. 2, 1995, pp.144,154

    Google Scholar 

  17. S. Patai, Z. Rappoport (Eds.), The Synthesis of Sulphones, Sulphoxides, and Cyclic Sulphides, Wiley, New York, 1994

    Google Scholar 

  18. N.S. Simpkins,in: J.E. Baldwin, P.D. Magnus, (Eds.), In Sulphones in Organic Synthesis, Pergamon: Oxford, 1993, p. 5.

    Google Scholar 

  19. E. Clark, in: J.I. Kroschwitz, M. Howe-Grant (Eds.), In Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed, Vol. 23, Wiley, New York, 1997, p.134

    Google Scholar 

  20. R. Willer, J.I. Kroschwitz, M. Howe-Grant (Eds.), In Kirk-Othmer Encyclopedia of Chemical Technology, 4th ed, Vol. 23, Wiley, New York, 1997, p. 217.

    Google Scholar 

  21. Y.-J. Chen, Y.-P. Huang, Tetrahedron Lett. 41 (2000) 5233.

    CAS  Google Scholar 

  22. A. Shaabani, M.B. Teimouri, H.R. Safaei, Synth. Commun. 30 (2000) 265.

    CAS  Google Scholar 

  23. A. Bravo, B. Dordi, F. Fontana, F. Minisci, J. Org. Chem. 66 (2001) 3232.

    CAS  Google Scholar 

  24. D.J. Procter, J. Chem. Soc., Perkin Trans. 1 (2001) 335.

    Google Scholar 

  25. F. Batigalhia, M. Zaldini-Hernandes, A.G. Ferreira, I. Malvestiti, Q.B. Cass, Tetrahedron 57 (2001) 9669.

    CAS  Google Scholar 

  26. S.E. Martin, L.I. Rossi, Tetrahedron Lett. 42(2001) 7147.

    CAS  Google Scholar 

  27. Z.-X. Xiong, N.-P. Huang, P. Zhong, Synth. Commun. 31 (2001) 245.

    CAS  Google Scholar 

  28. A.R. Hajipour, S.E. Mallakpour, H. Adibi, J. Org. Chem. 67 (2002) 8666.

    CAS  Google Scholar 

  29. B. Pelotier, M.S. Anson, I.B. Campbell, S.J.F. Macdonald, G. Priem, R.F.W. Jackson, Synlett (2002) 1055.

  30. S.S. Kim, K. Nehru, S.S. Kim, D.W. Kim, H.C. Jung, Synthesis (2002) 2484.

  31. H. Firouzabadi, M. Seddighi, Synth. Commun. 21 (1991) 211

    CAS  Google Scholar 

  32. H. Firouzabadi, I. Mohammadpoor-Baltork, Bull. Chem. Soc. Jpn. 65 (1992) 1131

    CAS  Google Scholar 

  33. N. Iranpoor, H. Firouzabadi, A.-R. Pourali, Tetrahedron,58 (2002) 5179

    CAS  Google Scholar 

  34. N. Iranpoor, H. Firouzabadi, A.-R. Pourali, Synlett (2004) 347.

  35. G. Kar, A.K. Saikia, U. Bora, S.K. Dehury, M.K. Chaudhuri, Tetrahedron Lett. 44 (2003) 4503.

    CAS  Google Scholar 

  36. W.L. Xu, Y.Z. Li, Q.S. Zhang, H.S. Zhu, Synthesis (2004) 227.

  37. K. Sato, M. Hyodo, M. Aoki, X.-Q. Zheng, R. Noyori, Tetrahedron 57 (2001) 2469.

    CAS  Google Scholar 

  38. K. Bahrami, Tetrahedron Lett. 47 (2006) 2009.

    CAS  Google Scholar 

  39. D.A. Evans, K.T. Chapman, J. Basaha, J. Am. Chem. Soc. 110 (1988) 1238.

    CAS  Google Scholar 

  40. M. Franck-Neumann, M. Miesch, L. Gross, Tetrahedron Lett. 31 (1990) 5027

    CAS  Google Scholar 

  41. M. Franck-Neumann, M. Miesch, L. Gross, Tetrahedron Lett. 33 (1992) 3879.

    CAS  Google Scholar 

  42. M.D. Groaning, G.P. Brengett, A.I. Meyers, J. Org. Chem. 63 (1998) 5517.

    CAS  Google Scholar 

  43. F. Sato, S. Sato, M. Sato, J. Organomet. Chem. 122(1976) C25

    CAS  Google Scholar 

  44. F. Sato, Y. Tomuro, H. Ishikawa, M. Sato, Chem. Lett. (1980) 99.

  45. N. Asao, J.X. Liu, T. Sudoh, Y. Xamamoto, J. Chem. Soc., Chem. Commun. (1995) 2405

  46. N. Asao, J.X. Liu, T. Sudoh, Y. Yamamoto, J. Org. Chem. 61 (1996)4568

    CAS  Google Scholar 

  47. N. Asao, Y. Matsukawa, Y. Yamamoto, J. Chem. Soc., Chem. Commun. (1996) 1513.

  48. P.G.M. Wuts, Green’s Protective Groups in Organic Synthesis, 4th ed, Wiley, New York, 2007.

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

  50. G. Smitha, C. Sanjeeva Reddy, Tetrahedron 59 (2003) 9571.

    CAS  Google Scholar 

  51. K. Ishihara, M. Nakayama, S. Ohara, H. Yamamoto, Tetrahedron 58 (2002) 8179.

    CAS  Google Scholar 

  52. K. Mantri, K. Komura, Y. Sugi, Green Chem. 7 (2005) 677.

    CAS  Google Scholar 

  53. A.K. Chakraborti, R. Gulhane, Synlett (2004) 627.

  54. R. Ghosh, S. Maiti, A.K. Chakraborty, Tetrahedron Lett. 46 (2005) 147.

    CAS  Google Scholar 

  55. G.V.M. Sharma, B. Srinivas, P.R. Krishna, Tetrahedron Lett. 44 (2003) 4689.

    CAS  Google Scholar 

  56. K. Purushothama Chary, G.H. Mohan, D.S. Iyenger, Chem. Lett. ( 1999) 1223.

  57. I. Stohrer, H.M. Hoffmann, Tetrahedron 48 (1992) 6021.

    CAS  Google Scholar 

  58. C.S. Reddy, G. Smitha, S. Chandrasekhar, Tetrahedron Lett. 44 (2003) 4693.

    CAS  Google Scholar 

  59. J.G. Smith, Synthesis (1984) 629.

  60. G.A. Kraus, P.J. Thomas, J. Org. Chem. 53 (1988)1395

    CAS  Google Scholar 

  61. W.S. Johnson, M.S. Plummer, S. Pulla Reddy, W.R. Bartlett, J. Am. Chem. Soc. 115 (1993) 515.

    CAS  Google Scholar 

  62. K.B. Sharpless, M.A. Umbreit, M.T. Nieh, T.C. Flood, J. Am. Chem. Soc. 94 (1972) 6538

    CAS  Google Scholar 

  63. M.A. Umbreit, K.B. Sharpless, Org. Synth. 60 (1981) 29

    CAS  Google Scholar 

  64. P. Dowd, K. Kang, Chem. Commun. (1974) 384

  65. P.F. Hudrlik, D. Peterson, R.J. Rona, J. Org. Chem. 40 (1975) 2263

    CAS  Google Scholar 

  66. M. Rosenblum, M.R. Saidi, M. Madhavarao, Tetrahedron Lett. 16 (1975) 4009

    Google Scholar 

  67. M.T.Reetz, M. Plackky, Synthesis (1976) 199

  68. K. Yamada, S. Goto, H. Nagase, Y. Kyotoni, Y. Hirata, J. Org. Chem. 43 (1978) 2076

    CAS  Google Scholar 

  69. P.E. Sonnet, Synthesis(1980) 828

  70. S. Matsobara, T. Nonaka, Y. Okuda, S. Kanemoto, K. Oshima, H. Nozaki, Bull. Chem. Soc. Jpn. (1985) 1480

  71. A. Ogawa, J.I. Miyake, S. Murai, N. Sonoda, Tetrahedron Lett. 26 (1985) 669.

    CAS  Google Scholar 

  72. G. Descotes (Ed.), Carbohydrates as Organic Raw Materials II; VCH, New York, 1993.

  73. C.W. Shoppee, S. Sternhell, W.C. Taylor, Aust. J. Chem. 19 (1966) 1265.

    Google Scholar 

  74. For a review see: M. Bartok, K.L. Lang, in: S. Patai (Ed.), The Chemistry of Ethers, Crown Ethers, Hydroxy Groups and Their Sulfur Analogues, Part I, Supplement E, John Wiley & Sons, New York, 1980, p. 609

    Google Scholar 

  75. T.J. Mason, Heterocyclic Chem. 3 (1982) 1

    CAS  Google Scholar 

  76. P.E. Sonnet,Tetrahedron 36 (1980) 557

  77. H. Alper, D. DesRoches, Tetrahedron Lett. (1977) 4155

  78. H. Suzuki, T.Fuchita, A. Iwasa, T. Mishina, Synthesis (1978) 905

  79. V. Calo, L. Lopez, A. Mincussi, G. Pesce, Synthesis(1976) 200

  80. K.N. Gurudutt, B. Ravindranath,Tetrahedron Lett. 21 (1980) 1173

    CAS  Google Scholar 

  81. D.L.J. Clive, S.M. Menchen, J. Org. Chem. 45 (1980) 2347

    CAS  Google Scholar 

  82. S. Togashi, J.G. Fulcher, B.R. Cho, M. Hasegawa, J.A. Gladysz, J. Org. Chem. 45 (1980) 3044.

    CAS  Google Scholar 

  83. M.G. Martin, B. Ganem, Tetrahedron Lett. 25 (1984) 251.

    CAS  Google Scholar 

  84. Z. Paryzek, R. Wydra, Tetrahedron Lett. 25 (1984) 2601.

    CAS  Google Scholar 

  85. A. Ogawa, J.I. Miyake, S. Murai, N. Sonoda, Tetrahedron Lett. 26 (1985) 669.

    CAS  Google Scholar 

  86. P.B. Grasse, B.E. Brauer, J.J. Zupancic, K.J. Kaufmann, G.B. Schuster, J. Am. Chem. Soc. 105(1983) 6833

    CAS  Google Scholar 

  87. D. Griller, L. Hadel, A.S. Nazran, M.S. Platz, P.C. Wong, J.G. Savino, J.C. Scaiano, J. Am. Chem. Soc. 106 (1984) 2227.

    CAS  Google Scholar 

  88. C.J. Shields, G.B. Schuster, Tetrahedron Lett. 28 (1987) 853.

    CAS  Google Scholar 

  89. R.B. Santos, T.J. Brocksom, U. Brocksom, Tetrahedron Lett. 38 (1997) 745.

    Google Scholar 

  90. H. Isobe, B.P. Branchaud, Tetrahedron Lett. 40 (1999) 8747.

    CAS  Google Scholar 

  91. G. Righi, P. Bouicelli, A. Sperandio, Tetrahderon, 56(2000) 1733

    CAS  Google Scholar 

  92. R. Antonioletti, P. Bovicelli, E. Fazzolari, G. Righi, Tetrahedron Lett. 41 (2000) 9315.

    CAS  Google Scholar 

  93. S. Kim, K. Hee Kim, J. Chem. Soc. Perkin Trans. 1 (1997) 1095.

    Google Scholar 

  94. K. Yachi, K. Maeda, H. Shinokubo, K. Oshima, Tetrahedron Lett. 38 (1997) 5161.

    CAS  Google Scholar 

  95. X. Wang, L.K. Woo, J. Org. Chem. 63 (1998) 356.

    CAS  Google Scholar 

  96. K.P. Gable, E.C. Brown, Organometallics 19 (2000)944

    CAS  Google Scholar 

  97. K.P. Gable, E.C. Brown, Synlett (2003) 2243.

  98. A. Patra, M. Bandyopadhyay, D. Mal, Tetrahedron Lett. 44 (2003) 2355.

    CAS  Google Scholar 

  99. H. Firouzabadi, N. Iranpoor, M. Jafarpour, Tetrahedron Lett. 46 (2005) 4107.

    CAS  Google Scholar 

  100. D.R. Gehlert, D.J. Goldstein, P.A. Hipskind, Ann. Rep. Med. Chem. (1999) 201

  101. E.J. Corey, F. Zhang, Angew. Chem., Int. Ed. 38 (1999) 1931

    CAS  Google Scholar 

  102. C.W. Johannes, M.S. Visser, G.S. Weatherhead, A.H. Hoveyda, J. Am. Chem. Soc. 120 (1998) 8340

    CAS  Google Scholar 

  103. B.L. Chng, A. Ganesan, Bioorg. Med. Chem. Lett. 7 (1997)1511

    CAS  Google Scholar 

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

    CAS  Google Scholar 

  105. J. De Cree, H. Geukens, J. Leempoels, H. Verhaegen, Drug Dev. Res. 8 (1986) 109.

    Google Scholar 

  106. P. O’Brien, Angew Chem., Int. Ed. 38 (1999) 326

    Google Scholar 

  107. G. Li, H.-T. Chang, K.B. Sharpless, Angew Chem., Int. Ed. 35 (1996) 451.

    CAS  Google Scholar 

  108. D.J. Ager, I. Prakash, D.R. Schaad, Chem. Rev. 96 (1996) 835.

    CAS  Google Scholar 

  109. S.C. Bergmeier, Tetrahedron 56 (2000) 2561

    CAS  Google Scholar 

  110. D.M. Hodgson, A.R. Gibbs, G.P. Lee, Tetrahedron 52(1996) 14361

    CAS  Google Scholar 

  111. R.M. Hanson, Chem. Rev. 91 (1991)437

    CAS  Google Scholar 

  112. O. Mitsunobu, in: E. Winterfeldt (Ed.), Comprehensive Organic Synthesis, Vol. 6, Pergamon Press, New York, 1996, Part 1.3.4.1

    Google Scholar 

  113. A.S. Rao, S.K. Paknikar, J.G. Kirtane, Tetrahedron 39 (1983) 2323.

    CAS  Google Scholar 

  114. P.A. Crooks, R. Szyudler, Chem. Ind., London, 1973,1111

  115. J.A. Deyrup, C.L. Moyer, J. Org. Chem. 34(1969) 175

    CAS  Google Scholar 

  116. M. Freifelder, G.R. Stone, J. Org. Chem.26 (1961) 1477

    CAS  Google Scholar 

  117. M. Mousseron, J. Jullien, Y. Jolchine, Bull. Soc. Chim. Fr. (1952) 757

    Google Scholar 

  118. R.E. Lutz, J.A. Freek, R.S. Murphy, J. Am. Chem. Soc. 70 (1948) 2015.

    CAS  Google Scholar 

  119. A.K. Chakraborti, A. Kondaskar, Tetrahedron Lett. 44 (2003) 8315.

    CAS  Google Scholar 

  120. Y.R. Santosh Laxmi, D.S. Iyengar, Synth. Commun. 27 (1997) 1731.

    CAS  Google Scholar 

  121. J.S. Yadav. R. Rayasekhar, M.S. R.Murty, Tetrahedron Lett. 46 (2005) 2311.

    CAS  Google Scholar 

  122. J. Villieras, C. Bacquet, J.F. Normant, Bull. Chem. Soc. Fr. (1975) 1797.

  123. W.F. Bailey, A.D. Khanolkar, J. Org. Chem. 55(1990) 6058

    CAS  Google Scholar 

  124. W.F. Bailey, A.D. Khanolkar,Tetrahedron 47 (1991) 7727.

    CAS  Google Scholar 

  125. H. Firouzabadi, N. Iranpoor, M. Jafarpour, Tetrahedron Lett. 45 (2004) 7451.

    CAS  Google Scholar 

  126. H.I. Moberg, J.R. Omnaas, J. Am. Chem. Soc. 107 (1985) 2986.

    Google Scholar 

  127. V.J. Hurby, F. Al-Obeidi, W. Kazmierski, Biochem. J. 268 (1990) 249.

    Google Scholar 

  128. T. Kataoka, D.D. Beusen, J.D. Clark, M. Yodo, G.R. Marshall, Biopolymers 32 (1992) 1519.

    CAS  Google Scholar 

  129. V.J. Hurby, G.G. Bonner, Methods in Molecular Biology 35 (1994) 201.

    Google Scholar 

  130. G. Solladie, Synthesis (1981) 185.

  131. G.H. Posner, in: S. Patai, Z. Rappoport, C.J.M. Sterling, (Eds.), The Chemistry of Sulfones and Sulfoxides, Wiley, Chichester, 1988, chap. 16.

  132. E.G. Mata, Phosphorus, Sulfur & Silicon 117 (1996) 231.

    CAS  Google Scholar 

  133. M.C. Carreno, Chem. Rev. 95 (1995) 1717.

    CAS  Google Scholar 

  134. L.A. Paquette, Synlett (2001) 1.

  135. C. Najera, J.M. Sansano, Recent Res. Devel. Org. Chem. 2 (1998) 637.

    CAS  Google Scholar 

  136. R. Chinchila, C. Najera, Recent Res. Devel. Org. Chem. 1 (1997) 437.

    Google Scholar 

  137. Q. Yao, Org. Lett. 4 (2002) 427.

    CAS  Google Scholar 

  138. H. Firouzabadi, N. Iranpoor, M. Jafarpour, Tetrahedron Lett. 47 (2006) 93.

    CAS  Google Scholar 

  139. V.Snieckus, The Alkaloids, Academic, Vol. 11, NewYork, 1968

  140. G.W. Gribble, Comperhensive Heterocyclic Chemistry, 2nd ed., Vol. 2, Pergamon, New York, 1996, p. 203

    Google Scholar 

  141. R. Gibe, M.A. Kerr, J. Org.Chem. 67 (2002) 6247.

    CAS  Google Scholar 

  142. M.S. Gibson, in: S. Patai (Ed.), The Chemistry of Amino Group, Interscience, New York, 1968, p. 61

    Google Scholar 

  143. J.P. Collman, B.M. Trost, T.R. Veroeven, in: G. Wilkinson, F.G.A. Stone (Eds.), Pergamon Press, Oxford, 1982, p. 892

  144. J. March, Advanced Organic Chemistry, 4th ed., Wiley, New York, 1992, p. 768.

    Google Scholar 

  145. R. Baltzly, E. Lorz, P.B. Russell, F.M. Smith, J. Am. Chem. Soc. 77 (1955) 624.

    CAS  Google Scholar 

  146. C.B. Pollard, G.C. Mattson, J. Am. Chem. Soc, 78 (1956) 4089

    CAS  Google Scholar 

  147. J. Staunton, B. Wilkinson, Top. Curr. Chem. 195 (1998) 49.

    CAS  Google Scholar 

  148. M. Tramontini, Synthesis (1973) 703.

  149. Y.F. Wang, T. Izawa, S. Kobayashi, M. Ohano, J. Am. Chem. Soc. 104 (1982) 6465.

    CAS  Google Scholar 

  150. G.I. Georg(Ed.), The Organic Chemistry of ß-Lactams, VCH Publishers, New York, 1993.

  151. Y. Hayashi, J.J. Rode, E.J. Corey, J. Am. Chem. Soc. 118 (1996) 5502.

    CAS  Google Scholar 

  152. E. Juariti(Ed.), Enantioselective Synthesis of ß-Amino Acids, Wiley-VCH, New York, 1997.

  153. S. Kobayashi, H. Ishitani, Chem. Rev. 99 (1999) 1069.

    CAS  Google Scholar 

  154. G. Cardillo, C. Tomasini, Chem. Soc. Rev. (1996)117

  155. E. Juaristi, H. Lopez-Ruiz, Curr. Med. Chem. 6 (1999) 983.

    CAS  Google Scholar 

  156. A. Graul, J. Castaner, Drugs Future 22 (1997) 956.

    CAS  Google Scholar 

  157. H. Firouzabadi, N. Iranpoor, F. Nowrouzi, Chem. Commun. (2005) 789 and references cited therein

  158. H. Firouzabadi, N. Iranpoor, A.A. Jafari, Adv. Synth. Catal. 347 (2005) 655 and references cited therein.

    CAS  Google Scholar 

  159. H. Firouzabadi, N. Iranpoor, M. Jafarpour, A. Ghaderi, J. Mol. Catal. A. 252 (2006) 150.

    CAS  Google Scholar 

  160. K.K.W. Lo, K.H.K. Tsang, W.K. Hui, N. Zhu, Chem. Commun. (2003) 2704.

  161. J.R. Plimmer, D.W. Gammon, N.N. Ragsdale, Encyclopedia of Agrochemicals, Vol. 3, John Wiley & Sons, New York, 2003.

  162. A. Ramirez, S. Garcia-Rubio, Curr. Med. Chem. 10 (2003) 1891.

    CAS  Google Scholar 

  163. S. Zhao, X. Liao, J.M. Cook, Org. Lett. 4 (2002) 687; and references cited therein.

    CAS  Google Scholar 

  164. D.J. Faulkner, Nat. Prod. Rep. 18 (2001) 1

    CAS  Google Scholar 

  165. F.Y. Miyake, K. Yakushijin, D.A. Horne, Org. Lett. 4 (2002)941

    CAS  Google Scholar 

  166. B. Jiang, C.G. Yang, J. Wang, J. Org. Chem. 67(2002) 1396.

    CAS  Google Scholar 

  167. B. Gregorovich, K. Liang, D. Chegston, S. Macdonald, Can. J. Chem. 46 (1968) 3291

    CAS  Google Scholar 

  168. M. Roomi, S. Macdonald, Can. J. Chem. 48 (1970) 139

    CAS  Google Scholar 

  169. Auria, Tetrahedron 47 (1991) 9225

    Google Scholar 

  170. R.J. Sundberg, The Chemistry of Indoles, Academic Press, New York, 1970.

  171. A. Chatterjee, S. Manna, J. Benerji, C. Pascard, T. Prange, J. Shoolery, J. Chem. Soc., Perkin Trans. 1 (1980) 553

    Google Scholar 

  172. W.E. Noland, M.R. Venkiteswaran, C.G. Richards, J. Org. Chem. 26 (1961) 4241

    CAS  Google Scholar 

  173. J.S. Yadav,B.V.S. Reddy, C.V.S.R. Mueth, G.M. Kumar, C.Madan, Synthesis (2001) 783

  174. J. Banerji, A. Chatterjee, S. Manna, C. Pascard, T. Prange, J.N. Shoolery, Heterocycles 15 (1981) 325

    CAS  Google Scholar 

  175. A. Chatterjee, R. Chakrabarthi, B. Das, S. Kanrar, J. Banerji, H. Budzikiewicz, A. Newman, T. Prange, Heterocycles 34 (1992) 259

    CAS  Google Scholar 

  176. R. Nagarajan, P.T. Perumal, Tetrahedron 58 (2002) 1229

    CAS  Google Scholar 

  177. R. Nagarajan, P.T. Perumal, Synth. Commun. 32 (2002) 105

    CAS  Google Scholar 

  178. G. Babu, N. Sridhar, P.T. Perumal, Synth. Commun. 30 (2000) 1609.

    CAS  Google Scholar 

  179. C. Ramesh, J. Banerjee, R. Pal, B. Das, Adv. Synth. Catal. 345 (2003) 557.

    CAS  Google Scholar 

  180. L. Yu, D. Chen, J. Li, P.G. Wang, J. Org. Chem. 62 (1997) 3575.

    CAS  Google Scholar 

  181. J. Li, M. Zhou, B. Li, G. Zhang, Synth. Commun. 34 (2004) 275

    CAS  Google Scholar 

  182. A.V. Reddy, K. Ravinder, V.L. N. Reddy, T.V. Goud, V. Ravikanth, Y. Venkateswarlu, Synth. Commun. 33 (2003) 3687.

    Google Scholar 

  183. S.J. Ji, M.F. Zhou, D.G. Gu, S.Y. Wang, T.P. Loh, Synlett (2003) 2077

  184. S.J. Ji, M.F. Zhou, D.G. Gu, Z. Q. Jiang, T.P. Loh, Eur. J. Org. Chem. (2004) 1584

  185. J.S. Yadav, B.V.S. Reddy, S. Sunitha, Adv. Synth. Catal. 345 (2003) 349.

    CAS  Google Scholar 

  186. B.P. Bandgar, K.A. Shaikh, Tetrahedron Lett. 44 (2003) 1959.

    CAS  Google Scholar 

  187. J.S. Yadav, B.V.S. Reddy, V.S.R. Murthy, G.M. Kumar, C. Madan, Synthesis (2001) 783.

  188. A.K. Maiti, P. Bhattacharyya, J. Chem. Res. (S) (1997) 424

  189. M. Chakrabarty, S. Sarkar, Tetrahedron Lett. 43 (2002) 1351

    CAS  Google Scholar 

  190. M. Chakrabarty, N. Ghosh, R. Basak, Y. Harigaya, Tetrahedron Lett. 43 (2002) 4075

    CAS  Google Scholar 

  191. A.K. Chakraborti, A. Kondaskar, S. Rudrawar, Tetrahedron 60 (2004) 9085.

    CAS  Google Scholar 

  192. D. Chen, L. Yu, P.G. Wang, Tetrahedron Lett. 37 (1996) 4467.

    CAS  Google Scholar 

  193. L. Wang, J.H. Han, T.J. Sheng, Z. Fan, X. Tang, Synlett (2005) 337.

  194. H. Firouzabadi, N. Iranpoor, A.A. Jafari, J. Mol. Catal. A. 244 (2006) 168.

    CAS  Google Scholar 

  195. H. Firouzabadi, N. Iranpoor, M. Jafarpour, A. Ghaderi, J. Mol. Catal. A. 253 (2006) 249.

    CAS  Google Scholar 

  196. J. March, Advanced Organic Chemistry, Benjamin, 4th ed., New York, 1992, p. 491.

  197. For example, K.P.C. Vollhardt, N.E. Schore, Organic Chemistry, 3rd ed., Freeman, New York, 1999, p. 1039.

    Google Scholar 

  198. Y. Tanabe, R. Hamasaki, S. Funakoshi, Chem. Commun. (2001) 1674.

  199. M. Shi, J.K. Jiang, S.C. Cui, Y.S. Feng, J. Chem. Soc., Perkin Trans. 1 (2001) 390, and references cited therein.

    Google Scholar 

  200. G. Wilkinson, J.M. Birmingham, J. Am. Chem. Soc. 76 (1954) 4281.

    CAS  Google Scholar 

  201. L.S. Hegedus, B.H. Lipshutz, J.A. Marshall, E. Nakamura, E. Negishi, M.T. Reetz, M.F. Semmelhack, K. Smith, H. Yamamoto, in: M. Schlosser (Ed.), Organometallics in Synthesis, 2th ed., John Wiley & Sons, Ltd., 2004, P. 925.

  202. J.G. Montana, N. Phillipson, R.J.K. Taylor, J. Chem. Soc., Chem. Commun. (1994) 2289.

  203. J.S. Yadav, B.U.S. Reddy, K.S. Ray, K.B. Reddy, A.R. Prasad, Synthesis (2001) 2277. [131] For selected recent examples, see

  204. T.R. Mano, W. Stevens, K. Ando, K. Nakao, Y. Okumura, M. Sakakibara, T. Okumura, T. Tamura, K. Miyamoto, Bioorg. Med. Chem. 11 (2003) 3879

    CAS  Google Scholar 

  205. K.J. Duffy, A.T. Price, E. Delorme, S.B. Dillon, C. Duquenne, C. Erickson-Miller, L. Giampa, Y. Huang, R.M. Keenan, P. Lamb, N. Liu, S.G. Miller, J. Rosen, A.N. Shaw, H. Smith, K.J. Wiggall, L. Zhang, J.I. Luengo, J. Med. Chem. 45 (2002) 3576

    CAS  Google Scholar 

  206. A. Tafi, R. Costi, M. Botta, R. Di Santo, F. Corelli, S. Massa, A. Ciacci, F. Manetti, M. Artico, J. Med. Chem. 45 (2002) 2720

    CAS  Google Scholar 

  207. J. Ohmori, M. Shimizu-Sasamata, M. Okada, S. Sakamoto, J. Med. Chem. 40 (1997) 2053

    CAS  Google Scholar 

  208. P.C. Astles, M.J. Ashton, A.W. Bridge, N.V. Harris, T.W. Hart, D.P. Parrott, B. Porter, D. Riddell, C. Smith, R.J. Williams, J. Med. Chem. 39 (1996) 1423.

    CAS  Google Scholar 

  209. S. Wendeborn, T. Winkler, I. Foisy, Tetrahedron Lett. 41 (2000) 6387, and references cited therein

    CAS  Google Scholar 

  210. H.B. Lee, S. Balasubramanian, Org. Lett. 2 (2000) 323 and references cited therein.

    CAS  Google Scholar 

  211. See for example: a) E. Kim, E.E. Chufa’n, K. Kamaraj, K.D. Karlin, Chem. Rev. 104 (2004) 1077

    CAS  Google Scholar 

  212. Z. He,.B. Colbran, D.C. Craig, Chem. Eur. J. 9 (2003) 116

    CAS  Google Scholar 

  213. D.T. Hill, G.R. Girard, J. Weinstock, R.M. Edwards, E.F. Weidley, E. Ohlstein, C.E. Peishoff, E. Baker, N. Aiyar, Bioorg. Med. Chem. Lett. 5 (1995) 19

    CAS  Google Scholar 

  214. S.K. Thompson, K.H.M. Murthy, B. Zhao, E. Winborne, D. W. Green, S.M. Fisher, R.L. DesJarlais, T.A. Tomaszek Jr., T.D. Meek, J.G. Gleason, S.S. Abdel-Meguid, J. Med. Chem. 37 (1994) 3100

    CAS  Google Scholar 

  215. D.M. Rotstein, D.J.K. Kertesz, A.M. Walker, D.C. Swinney, J. Med. Chem. 35 (1992) 2818.

    CAS  Google Scholar 

  216. S. Bombek, R. Lenarsic, M. Kocevar, S. Polanc, Synlett (2001) 1237

  217. S. Bombek, F. Pozgan, M. Kocevar, S. Polanc, New J. Chem. 29 (2005) 948.

    CAS  Google Scholar 

  218. A. Vaitiekunas, F.F. Nord, J. Am. Chem. Soc. 75 (1953) 1764

    CAS  Google Scholar 

  219. J.H. Wotiz, F. Huba, J. Org. Chem. 24 (1959) 595.

    CAS  Google Scholar 

  220. J.F. Bunnett, C.E. Moyer, Jr., J. Am. Chem. Soc. 93 (1971) 1183

    CAS  Google Scholar 

  221. J.F. Bunnett, Acc. Chem. Res. 5 (1972) 139, and references therein

    CAS  Google Scholar 

  222. M.H. Mach, J.F. Bunnett, J. Org. Chem. 45 (1980) 4660

    CAS  Google Scholar 

  223. G. Quéguiner, F. Marsais, V. Snieckus, J. Epsztajn, Adv. Heterocycl. Chem. 52 (1991) 187, and references therein.

    Google Scholar 

  224. F. Toudic, N. Ple, A. Turck, G. Quéguiner, Tetrahedron 58 (2002) 283

    CAS  Google Scholar 

  225. A. Godard, P. Rocca, F. Guillier, G. Duvey, F. Nivoliers, F. Marsais, G. Quéguiner, Can. J. Chem. 79 (2001) 1754

    CAS  Google Scholar 

  226. E. Arzel, P. Rocca, P. Grellier, M. Labaeïd, F. Frappier, F. Guéritte, C. Gaspard, F. Marsais, A. Godard, G. Quéguiner, J. Med. Chem. 44 (2001) 947

    Google Scholar 

  227. E. Arzel, P. Rocca, F. Marsais, A. Godard, G. Quéguiner, Tetrahedron 55 (1999) 12149

    CAS  Google Scholar 

  228. E. Arzel, P. Rocca, F. Marsais, A. Godard, G. Quéguiner, Heterocycles 50 (1999) 215

    CAS  Google Scholar 

  229. E. Arzel, P. Rocca, F. Marsais, A. Godard, G. Quéguiner, Tetrahedron Lett. 39 (1998) 6465

    CAS  Google Scholar 

  230. N. Ple, A. Turck, A. Heynderickx, G. Quéguiner, Tetrahedron 54 (1998) 9701

    CAS  Google Scholar 

  231. N. Ple, A. Turck, A. Heynderickx, G. Quéguiner, Tetrahedron 54 (1998) 4899

    CAS  Google Scholar 

  232. F. Trecourt, B. Gervais, M. Mallet, G. Quéguiner, J. Org. Chem. 61 (1996) 1673

    CAS  Google Scholar 

  233. C.Cochennec, P. Rocca, F. Marsais, A. Godard, G. Quéguiner, Synthesis (1995) 321

  234. F. Guiller, F. Nivoliers, A. Godard, F. Marsais, G. Quéguiner, Tetrahedron Lett. 35 (1994) 6489

    Google Scholar 

  235. N. Ple, A. Turck, K. Couture, G. Quéguiner, Tetrahedron 50 (1994) 10299

    CAS  Google Scholar 

  236. P. Rocca, C. Cochennec, F. Marsais, L. Thomasditdumont, M. Mallet, A. Godard, G. Quéguiner, J. Org. Chem. 58 (1993) 7832

    CAS  Google Scholar 

  237. F. Marsais, P. Pineau, F. Nivolliers, M. Mallet, A. Turck, A. Godard, G. Quéguiner, J. Org. Chem. 57 (1992) 565.

    CAS  Google Scholar 

  238. For very recent review, see: M. Schlosser, Eur. J. Org. Chem. (2001) 3975.

  239. See also: C. Bobbio, M. Schlosser, Eur. J. Org. Chem. (2001) 4533

  240. E. Castagnetti, M. Schlosser,Eur. J. Org. Chem. (2001) 3991

  241. F. Mongin, E.Marzi, M. Schlosser, Eur. J. Org. Chem. (2001) 2771

  242. E. Marzi, A. Bigi, M. Schlosser, Eur. J. Org. Chem. (2001) 1371

  243. F. Mongin, O. Desponds, M. Schlosser, Tetrahedron Lett. 37 (1996) 2767.

    CAS  Google Scholar 

  244. For recent achievements by other groups, see, for example: E. Lukevics, P. Arsenyan, S. Belyakov, J. Popelis, O. Pudova, Tetrahedron Lett. 42 (2001) 2039

    CAS  Google Scholar 

  245. I. Collins, J. Chem. Soc., Perkin Trans. 1 (2000)2845

    Google Scholar 

  246. R.J. Mattson, C.P. Sloan, C.C. Lockhart, J.D. Catt, Q. Gao, G.S. Huan, J. Org. Chem. 64 (1999) 8004

    CAS  Google Scholar 

  247. G. Consiglio, D. Spinelli, C. DellAErba, M. Novi, G. Petrillo, Gazz. Chim. Ital. 127 (1997) 753

    CAS  Google Scholar 

  248. P. Bjork, J. Malm, A.B. Hornfeldt, S. Gronowitz, Heterocycles, 44 (1997) 237

    Google Scholar 

  249. A.G. Giumanini, G. Verardo, P. Geatti, P. Strazzolini, Tetrahedron 52 (1996) 7137

    CAS  Google Scholar 

  250. J. Frohlich, C. Hametner, W. Kalt, Monatsh. Chem. 127 (1996) 325

    Google Scholar 

  251. J. Frohlich, C. Hametner, Monatsh. Chem. 127 (1996) 435

    Google Scholar 

  252. J. Frohlich, Bull. Soc. Chim.Belg. 105 (1996) 615

    CAS  Google Scholar 

  253. D.L. Comins, J.K. Saha,Tetrahedron Lett. 36 (1995) 7995

    CAS  Google Scholar 

  254. M. Belohradsky, P. Holy, J. Zavada, J. Chem. Soc., Perkin Trans. 2 (1995) 1853

    Google Scholar 

  255. P. Bury, G. Hareau, P. Kocienski, D. Dhanak, Tetrahedron 50 (1994) 8793

    CAS  Google Scholar 

  256. D.W. Hawkins, B.D. Iddon, S. Longthorne, P.J. Rosyk, J. Chem. Soc., Perkin Trans. 1 (1994) 2735.

    Google Scholar 

  257. M.B. Smith, J. March, March’s Advanced Organic Chemistry: Reactions, Mechanisms, and Structures, 5th ed., Wiley, New York, 2001, p. 735, and references therein.

    Google Scholar 

  258. A.R. Butler, A.P. Sanderson, J. Chem. Soc., Perkin Trans. 2 (1972) 989.

    Google Scholar 

  259. Y. Muramoto, H. Asakura, H. Suzuki, Nippon Kagaku Kaishi, 1992, 172.

  260. J.M. Brittain, P.B.D. dela Mare, P.A. Newman, Tetrahedron Lett. 21 (1980) 4111.

    CAS  Google Scholar 

  261. J.-C. Jacquesy, M.-P. Jouannetaud, Tetrahedron Lett. 23 (1982) 1673.

    CAS  Google Scholar 

  262. R.G.F. Giles, I.R. Green, L.S. Knight, V.R.L. Son, P. R.K. Mitchell, S.C. Yorke, J. Chem. Soc., Perkin Trans. 1 (1994) 853.

    Google Scholar 

  263. R.G.F. Giles, I.R. Green, L.S. Knight, V.R.L. Son, S.C. Yorke, J. Chem. Soc., Perkin Trans. 1 (1994) 865.

    Google Scholar 

  264. J.B. Press, N.H. Eudy, J. Heterocycl. Chem. 18 (1981) 1262.

    Google Scholar 

  265. R. Lenarsic, M. Kocevar, S. Polanc, J. Org. Chem. 64 (1999) 2558.

    CAS  Google Scholar 

  266. S. Bombek, R. Lenarsic, M. Kocevar, L. Saint-Jalmes, J. Roger Desmurs, S. Polanc, Chem. Commun. (2002) 1494.

  267. I. Mohammadpoor-Baltork, A.R. Khosropour, S.F. Hojati, Cat. Commun. 8 (2007) 200.

    CAS  Google Scholar 

  268. B. Eftekhari-Sis, A. Abdollahifar, M.M. Hashemi, M. Zirak, Eur. J. Org. Chem. (2006) 5152.

  269. V. Mirkhani, I. Mohammadpoor-Baltork, M. Moghadam, S. Tangestaninejad, M. Abdollahi-Alibeik, H. Kargar, Appl. Catalysis A: General 325 (2007) 99.

    CAS  Google Scholar 

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  1. Department of Chemistry, College of Sciences, Shiraz University, Shiraz, 71454, Iran

    H. Firouzabadi & M. Jafarpour

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Firouzabadi, H., Jafarpour, M. Some applications of zirconium(IV) tetrachloride (ZrCl4) and zirconium(IV) oxydichloride octahydrate (ZrOCl2.8H2O) as catalysts or reagents in organic synthesis. JICS 5, 159–183 (2008). https://doi.org/10.1007/BF03246110

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