Microwaves, power ultrasound, and ionic liquids. A new synergy in green organic synthesis

Chimia

Volumn 60, Issue 6, 2006, Pages 313-320

  Lévêque, Jean Marc ^a   Cravotto, Giancarlo ^b  

^a UNIVERSITÉ DE SAVOIE   (France)

^b UNIVERSITY OF TURIN   (Italy)

Author keywords

Combined irradiation; Ionic liquids; Microwaves; Power ultrasound; Synthesis

Indexed keywords

EID: 33746018015     PISSN: 00094293     EISSN: None     Source Type: Journal    
DOI: 10.2533/000942906777836255     Document Type: Review

References (119)

1. M. Maeda, H. Amemiya, New J. Chem. 1995, 19, 1023.
2. G. Cravotto, S. Di Carlo, V. Tumiatti, C. Roggero, D. Bremner, Environ. Technol. 2005, 26, 721.
3. A. Cartellieri, RH. Thiesen, B. Niemeyer, Waste Management 2005, 25, 985.
4. M.D. Luque de Castro, M.M. Jimènez-Carmona, V. Fernandez-Pèrez, Trends in Anal. Chem. 1999, 18, 708.
5. W.S. Chu, Q. Liang, J.L. Liu, M.Q. Wei, M. Winters, L. Liotta, G. Sandberg, M.K. Gong, Lab. Investig. 2005, 85, 1416.
6. R. Sanghi, S.S. Kannamkumarath, J. Anal. Chem. 2004, 59, 1032.
7. Y. Mastai, A. Gedanken, in 'Chemistry of Nanomaterials' Ed. C.N.R. Rao, A. Mueller, A.K. Cheetham, 1, 113. Wiley-VCH, 2004.
8. C.O. Kappe, Angew. Chem. Int. Ed. 2004, 43, 6250.
9. L. Ferreux, A. Loupy, 'Microwaves in Organic Synthesis', Ed. A. Loupy, Wiley-VCH, 2002.
10. G. Cravotto, P. Cintas, Chem. Soc. Rev. 2006, 35, 180.
11. B. Toukoniitty, J.P. Mikkola, D.Y. Murzin, T. Salmi, Appl. Catal. A 2005, 279, 1.
12. G. Cravotto, L. Boffa, M. Turello, M. Parenti, A. Barge, Steroids 2005, 70, 77.
13. W. Bonrath, Ultrason. Sonochem. 2004, 11, 1.
14. V. Roy, L. Colombeau, R. Zerrouki, P. Krausz, Carbohydr. Res. 2004, 339, 1829.
15. M. Nuchter, B. Ondruschka, W. Bonrath, A. Gum, Green Chem. 2004, 6, 128.
16. S.E. Wolkenberg, W.D. Shipe, C.W. Lindsley, J.P. Guare, J.M. Pawluczyk, Curr. Opin. Drug Disc. & Devel. 2005, 8, 701.
17. T.J. Mason, D. Peters, 'Practical Sonochemistry. Power Ultrasound: Uses and Applications', Ellis Horwood, Chichester, 2002.
18. T.J. Mason, J. Lorimer, 'Applied Sonochemistry: Uses of Power Ultrasound in Chemistry and Processing', Wiley-VCH, 2002.
19. A. Lagha, S. Chemat, P.V. Bartels, F. Chemat, Analusis 1999, 27, 452.
20. Y. Peng, G. Song, Green Chem. 2001, 3, 302.
21. Y. Peng, G. Song, Green Chem. 2002, 4, 349.
22. Y. Peng, G. Song, Green Chem. 2003, 5, 704.
23. F. Chemat, M. Poux, J.L. Di Martino, J. Berlan, J. Microw. Power Electrom. En. 1996, 31, 19.
24. F. Chemat, M. Poux, S.A. Galema, J. Chem. Soc., Perkin Trans. 2 1997, 2371.
25. S. Chemat, A. Lagha, H.A. Amar, F. Chemat, Ultrason. Sonochem. 2004, 11, 5.
26. G. Cravotto, M. Beggiato, G. Palmisano, J.M. Levêque, W. Bonrath, Tetrahedron Lett. 2005, 46, 2267.
27. Y. Peng, R. Dou, G. Song, J. Jiang, Synlett 2005, 14, 2245.
28. P. Wasserscheid, T. Welton, 'Ionic liquids in synthesis', Wiley-VCH, 2002.
29. D.J.A.C.E. Tucker, Tet. Lett. 1989, 30, 1785;
30. J. Howarth, K.H.D. Fayne, P. McCormac, Tet. Lett. 1997, 38, 3097;
31. C.W. Lee, Tet. Lett. 1999, 40, 2461;
32. T. Fischer, A.S.T. Welton, J. Woolf, Tet. Lett. 1999, 40, 793;
33. F.Z.A.T Kitazume, Green Chem. 2000, 2, 137;
34. A.P. Abbott, G.C.D.L. Davies, R. K. Rasheed, V. Tambyrajah, Green Chem. 2002, 4, 24.
35. A. Starck, B.L. MacLean, R.D. Singer, J. Chem. Soc., Dalton Trans. 1999, 63;
36. S.J. Nara, J.R. Harjani, M. Salunkhe, J. Org. Chem. 2001, 66, 8616;
37. Z. Zhao, Z.L.G. Wang, W. Qiao, L. Cheng, Appl. Catal. A 2004, 262, 69.
38. W.A. Herrmann, V.P.W. Böhm, J. Organometal. Chem. 1999, 572, 141;
39. A. J. Carmichael, M.J. Earle, J.D. Holbrey, P.B. McCormac, K.R. Seddon, Org. Lett. 1999, 7, 997;
40. L. Xu, W. Chen, J. Xiao, Organometal. 2000, 19, 1123;
41. B.M. Choudary, S.M. Naidu, S. Chowdari, M.L. Kantam, B. Sreedhar, J. Am. Chem. Soc. 2002, 124, 14127;
42. F. Berthiol, M. Feuerstein, H. Doucet, M. Santelli, Tet. Lett. 2002, 43, 5625;
43. G. Zou, Z. Wang, J. Zhu, J. Tang, M. H. He, J. Mol. Catal. A: Chem. 2003, 206, 193;
44. S.A. Forsyth, H.Q.N. Gunaratne, C. Hardacre, A. McKeown, D.W. Rooney, K.R. Seddon, J. Mol. Catal. A: Chem. 2005, 231, 61.
45. B.M. Choudary, S.M. Naidu, S. Chowdari, M.L. Kantam, B. Sreedhar, J. Am. Chem. Soc. 2002, 124, 14127;
46. G. Zou, Z. Wang, J. Zhu, J. Tang, M.H. He, J. Mol. Catal. A: Chem. 2003, 206, 193;
47. C.J. Mathews, P.J. Smith, T. Welton, J. Mol. Catal. A: Chem. 2004, 214, 27;
48. A. Corma, H. Garcia, A. Leyva, Tetrahedron 2005, 61, 9848.
49. S.-L. Chen, S.-J. Ji, T.-P. Loh, Tet. Lett. 2003, 44, 2405;
50. X.-F. Yang, M. Wang, R.S. Varma, C.-J. Li, J. Mol. Catal. A: Chem. 2004, 214, 147;
51. S. Sahoo, T. Joseph, S.B. Halligudi, J. Mol. Catal. A: Chem. 2005, 244, 179.
52. M.M. Dell'Anna, P. Mastrorilli, C.F. Nobile, G. Romanazzi, G.-P. Suranna, Chem. Commun. 2002, 434;
53. R.T. Dere, R.R. Pal, P.S. Patil, M.M. Salunkhe, Tet. Lett. 2003, 44, 5351;
54. V. Gallo, P. Mastrorilli, C.F. Nobile, G.-P. Suranna, Y. Wang, J. Organometal. Chem. 2005, 690, 3535.
55. J. Howarth, Tet. Lett. 2000, 41, 6627;
56. R. Bernini, A. Coratti, G. Fabrizi, A.Goggiamani, Tet. Lett. 2003, 44, 8991;
57. R. Bernini, E. Mincione, A. Coratti, G. Fabrizi, G. Battistuzzi, Tetrahedron 2004, 60, 967;
58. A. Ansari, S. Joyasawal, M.K. Gupta, J.S. Yadav, R. Gree, Tet. Lett. 2005, 46, 7507.
59. Y. Chauvin, L. Mussmann, H. Olivier, Angew. Chem. Int. Ed. Engl. 1995, 34, 2698;
60. P.A.Z. Suarez, J.E.L. Dullius, S. Einloft, R.F. De Souza, J. Dupont, Polyhedron 1996, 15, 1217;
61. R.A. Brown, E. Mckoon, C.A. Eckert, C.L. Liotta, P.O. Jessop, J. Am. Chem. Soc. 2001, 123, 1254;
62. J. Dupont, O.S. Fonseca, A.P. Umpierre, P.F.P Fichtner, S.R. Teixeira, J. Am. Chem. Soc. 2002, 124, 4228;
63. P.J. Dyson, D.J. Ellis, W. Henderson, G. Laurenczy, Adv. Synth. Catal. 2003, 345, 216;
64. D.-Q. Xu, Z.-Y. Hu, W.-W. Li, S.-P. Luo, Z.-Y. Wu, J. Mol. Catal. A: Chem. 2005, 255, 137.
65. A.E. Visser, R.P. Swatloski, R.D. Rogers, Green Chem. 2000, 1, 1;
66. A.E. Visser, R.P. Swatloski, W.M. Reichert, R. Mayton, S. Sheff, A. Wierzbicki, J.H. Davis, R.D. Rogers, Chem. Commun. 2001, 135.
67. R.P. Swatlosky, S.K. Spear, J.D. Holbrey, R.D. Rogers, J. Am. Chem. Soc. 2002, 124, 4974;
68. Y. NuLi, J. Yang, R. Wu, Electrochem. Commun. 2005, 7, 1105.
69. M.T. Reetz, W. Wiesenhöfer, G. Francio, W. Leitner, Chem. Commun. 2002, 992;
70. M. Persson, U.T Bornscheuer, J. Mol. Catal. B: Enzym. 2003, 22, 21;
71. N. Jain, A. Kumar, S. Chauhan, S.M.S. Chauhan, Tetrahedron 2005, 61, 1015.
72. A.J. Carmichael, D.M. Haddleton, S.A.F. Bon, K.R. Seddon, Chem. Commun. 2000, 1237;
73. S. Ferner, T.P. Davis, A.J. Carmichael, D.M. Haddleton, Eur. Polymer J. 2003, 39, 417.
74. N. Papageorgiou, M. Armand, P. Bonhôte, H. Pettersson, A. Azam, M. Grätzel, J. Electrochem. Soc. 1996, 143, 3099.
75. P. Wasserscheid, T. Welton, 'Ionic liquids in synthesis', Wiley-VCH, Weinheim, 2002;
76. T. Welton, Coordination Chem. Rev. 2004, 248, 2459.
77. C. Baudequin, J. Baudoux, J. Levillain, D. Cahard, A.-C. Gaumont, J.-C. Plaquevent, Tet. Asym. 2003, 14, 3081.
78. P. Wasserschied, A. Bösmann, C. Bolm, Chem. Commun. 2002, 200;
79. Z. Wang, Q. Wang, Y. Zhang, W. Bao, Tet. Lett. 2005, 46, 4657.
80. N.Z. Menschutkin, Phys. Chem. 1890, 6, 41;
81. J.A. Zoltewicz, L.W. Deady, Adv. Heterocycl. Chem. 1978, 22, 71.
82. R. Bohlmann, in 'Comprehensive Organic Synthesis', Ed. B.M. Trost, I. Fleming, Pergamon Press, Oxford, 1991, vol. 6, pp. 203.
83. R.A. Carpio, L.A. King, R.E. Lindstrom, J.C. Nardi, C.L. Hussey, J. Electrochem. Soc.: Electrochem. Sci. Technol. 1979, 126, 1644;
84. J.S. Wilkes, J.A. Levisky, A.W. Robert, C.L. Hussy, Inorg. Chem. 1982, 21, 1263.
85. L. Perreux A. Loupy, 'Microwaves in Organic Synthesis', Ed. A. Loupy, Wiley-VCH, Weinheim, 2002.
86. R.S. Varma, V.V. Namboodiri, Chem. Commun. 2001, 643.
87. B.M. Khadilkar, G.L. Rebeiro, Org. Proc. Res. & Dev. 2002, 6, 826.
88. M. Deetlefs, K.R. Seddon, Green Chem. 2003, 5, 181.
89. V.V. Namboodiri, R.S. Varma, Tet. Lett. 2002, 43, 5381.
90. V.V. Namboodiri, R.S. Varma, Chem. Commun. 2002, 916.
91. V.V. Namboodiri, R.S. Varma, Chem. Commun. 2002, 916;
92. Y.J. Kim, R.S. Varma, Tet. Lett. 2005, 46, 7447.
93. Y.J. K im, R.S. Varma, Tet. Lett. 2005, 46, 1467.
94. V. Singh, S. Kaur, V. Sapehiyia, J. Singh, G.L. Kad, Cat. Commun. 2005, 6, 57.
95. G. Vo Thanh, B. Pegot, A. Loupy, Eur. J. Org. Chem. 2004, 1112.
96. V.V. Namboodiri, R.S. Varma, Org. Lett. 2002, 4, 3161.
97. J.M. Lévêque, S. Desset, J. Suptil, C. Fachinger, M. Draye, W. Bonrath, G. Cravotto, Ultrason. Sonochem. 2006, 13, 189.
98. J.M. Lévêque, J.L. Luche, C. Pétrier, R. Roux, W. Bonrath, Green Chem. 2002, 4, 357.
99. K.S.A. Vallin, P. Emilsson, M. Larhed, A. Hallberg, J. Org. Chem. 2002, 67, 6243;
100. X. Xie, J. Lu, B. Chen, J. Han, X. She, X. Pan, Tet. Lett. 2004, 45, 809.
101. M.-C. Liao, X.-H. Duan, Y.-M. Liang, Tet. Lett. 2005, 46, 3469.
102. Z.F. Dörwald in Organic Synthesis on Solid Phase', Wiley-VCH, Weinheim, 2000.
103. J. Fraga-Dubreuil, J.-P. Bazureau, Tetrahedron 2003, 59, 6121.
104. H. Hakkou, J.-J. VanDen Eynde, J. Hamelin, J.-P. Bazureau, Tetrahedron 2004, 60, 3745.
105. J.-J. Legeay, J.-J. Vanden Eynde, J.-P. Bazureau, Tetrahedron 2005, 61, 12386;
106. F. Yi, Y. Peng, G. Song, Tet. Lett. 2005, 46, 3931.
107. Y.-H. Yen, Y-H. Chu, Tet. Lett. 2004, 45, 8137.
108. E. Van Der Eycken, P. Appukkuttan, W. De Borggraeve, W. Dehaen, D. Dallinger, C.O. Kappe, J. Org. Chem. 2002, 67, 7904.
109. R.X. Ren, J.X. Wu, Org. Lett. 2001, 3, 3727;
110. R.X. Ren, J.X. Wu, Tet. Lett. 2002, 43, 387.
111. N.B. Leadbeater, H.M. Torenius, H. Tye, Tetrahedron 2003, 59, 2253.
112. B.C. Ranu, R. Jana, J. Org. Chem. 2005, 70, 8621.
113. J. Fraga-Dubreuil, K. Bourahla, M. Rahmouni, J.-P. Bazureau, J. Hamelin, Catal. Commun. 2002, 5, 185.
114. D.J. Falnnigan, S.D. Hopkins, K.S. Suslick, J. Organometal. Chem. 2005, 690, 3513.
115. R. Rajagopal, K.V. Srinivasan, Ultrason. Sonochem. 2003, 10, 41.
116. R. Rajagopal, D.V. Jarijote, K.V. Srinivasan, Chem. Commun. 2002, 616.
117. R. Rajagopal, D.V. Jarijote, K.V. Srinivasan, Chem. Commun. 2001, 1544.
118. Z. Yingghuai, J. Phys. Chem. Solids 2004, 65, 349.
119. J.L. Bravo, I. Lopez, P. Cintas, G. Dilvero, MJ. Arévalo, Ultrason. Sonochem. in press DOI:10.1016/j.ultsonch.2005.07.001.