Microwave-promoted organic synthesis using ionic liquids: A mini review

Combinatorial Chemistry and High Throughput Screening

Volumn 7, Issue 5, 2004, Pages 511-528

  Leadbeater, Nicholas E ^a   Torenius, Hanna M ^b   Tye, Heather ^c  

^a UNIVERSITY OF CONNECTICUT   (United States)

^b KING'S COLLEGE LONDON   (United Kingdom)

^c EVOTEC UK LTD   (United Kingdom)

Author keywords

Fast reactions; Ionic liquids; Microwave heating; Organic synthesis

Indexed keywords

IONIC LIQUID; REAGENT; SOLVENT;

CATALYST; CHEMICAL COMPOSITION; CHEMICAL INTERACTION; CHEMICAL REACTION; CHEMISTRY; HEATING; ION TRANSPORT; LIQUID; MICROWAVE COOKING; MICROWAVE RADIATION; PRIORITY JOURNAL; REACTION TIME; SHORT SURVEY; SYNTHESIS; THERMOSTABILITY; VAPOR PRESSURE;

EID: 4243096265     PISSN: 13862073     EISSN: None     Source Type: Journal    
DOI: 10.2174/1386207043328562     Document Type: Short Survey

References (115)

1. For reviews and books on microwave heating in synthesis a) Caddick S. Tetrahedron, 1995, 38, 10403.
2. b) Berlan, J. Radiat. Phys. Chem., 1995, 45, 581.
3. c) Strauss, C. R. Aust. J. Chem., 1999, 52, 83.
4. d) Lindström, P.; Tierney, J.; Wathey, B.; Westman, J. Tetrahedron, 2001, 57, 9225.
5. e) Perreux, L.; Loupy A. Tetrahedron, 2001, 57, 9199.
6. f) Loypy, A. Microwaves in Organic Synthesis, Wiley-VCH, Wenheim 2002, Hayes, B. L. Microwave synthesis: Chemistry at the Speed of Light, CEM Publishing, Matthews, 2002.
7. f) Loypy, A. Microwaves in Organic Synthesis, Wiley-VCH, Wenheim 2002, Hayes, B. L. Microwave synthesis: Chemistry at the Speed of Light, CEM Publishing, Matthews, 2002.
8. For examples see: a) Westman, J. Org. Lett., 2001, 3, 3745.
9. b) Kuhnert, N.; Danks, T. N. Green Chem., 2001, 3, 68.
10. c) Loupy, A.; Regnier, S. Tetrahedron Lett., 1999, 40, 6221.
11. Kappe, C. O. Curr. Opin. Chem. Biol., 2002, 6, 314.
12. Lew, A.; Krutzik, P. O.; Hart, M. E., Chamberlin, A. R. J. Comb. Chem., 2002, 4, 95.
13. a) Larhed, M.; Hallberg, A., DDT, 2001, 6, 406.
14. b) Wathey, B.; Tierney, J.; Lindström, P.; Westman, J. Drug Disc. Today, 2002, 7, 373.
15. Kang, Y.; Mei, Y.; Du, Y.; Jin, Z. Org. Lett., 2003, 5, 4481.
16. Gedye, R.; Smith, F.; Westaway, K.; Humera, A.; Baldisera, L.; Laberge, L.; Roussell, L. Tetrahedron Lett., 1986, 27, 279.
17. Gigure, R.; Bray, T. L.; Duncan, S. M.; Majetich, G. Tetrahedron Lett., 1986, 27, 4945.
18. Baghurst, D. R.; Mingos, D. M. P. J. Organometal. Chem., 1990, C57.
19. Baghurst, D. R.; Mingos, D. M. P. J. Chem. Soc. Dalton Trans., 1992, 1151.
20. Stadler, A.; Yousefi, B. H.; Dallinger, D.; Walla, P.; Van der Eycken, E.; Kaval, N.; Kappe, C. O. Org. Process Res. Dev., 2003, 7, 707.
21. For reviews on the microwave dielectric heating see a) Gabriel, G.; Gabriel, S.; Grant, E. H.; Halstead, B. S.; Mingos, D. M. P. Chem. Soc. Rev., 1998, 27, 213.
22. Wilkes, J. S.; Levisky, J. A.; Wilson, R. A.; Hussey, C. L. Inorg. Chem., 1982, 21, 1263.
23. For ionic liquid synthesis see for example:Wasserscheid, P.; Welton, T., Ionic Liquids in Synthesis, Wiley-VCH, Weinheim, 2003.
24. For reviews on the synthesis and catalysis using ionic liquids see a) Welton, T. Chem. Rev., 1999, 99, 2071.
25. b) Olivier, H. J. Mol. Cat A., 1999, 146, 285.
26. c) Wassercheid, P. Keim, W., Angew. Chem. Int. Ed., 2000, 39, 3772.
27. d) Gordon, C. M. Appl. Cat. A., 2001, 101.
28. e) Kuhnert, N. Nachrichten aus der Chemie, 2001, 49, 306.
29. f) Sheldon, R. Chem. Commun., 2001, 2399.
30. g) Dupont, J.; De Souza, R. F.; Suarez, P. A. Z. Chem Rev., 2002, 102, 3667.
31. h) Zhao, D.; Wu, M.; Kou, Y.; Min, E. Catalysis Today, 2002, 74, 157.
32. i) Olivier-Bourbigou, H.; Magna, L. J. Mol. Cat. A., 2002, 3484, 1.
33. Aki, S. N. V. K.; Brennecke, J.; Samanta, A. Chem. Commun., 2001, 413.
34. Anderson, J. L.; Ding, J.; Welton, T.; Armstrong, D. W. J. Org. Chem., 2002, 124, 14247.
35. Asaki, M. L. T.; Redondo, A.; Zawodzinski, T. A.; Taylor, A. J. J. Chem. Pys., 2002, 116, 10377.
36. Larsen, A. S.; Holbrey, J. D.; Tham, F. S.; Reed, C. A. J. Am. Chem. Soc., 2000, 122, 7264.
37. Yanes, E. G.; Gratz, S. R.; Baldwin, M. J.; Robinson, S. E.; Stalcup, A. M. Anal. Chem., 2001, 3833.
38. Patent WO 00/72956
39. Varma, R. S.; Namboodiri, V. V. Chem. Commun., 2001, 643.
40. Namboodiri, V. V.; Varma, R. S. Tetrahedron Lett., 2002, 43, 5381.
41. Murugesan, S.; Karst, N.; Islam, T.; Wiencek, J. M.; Linhardt, R. J. Synlett., 2003, 9, 1283.
42. Namboodiri, V. V.; Varma, R. S. Chem. Commun., 2002, 24, 342.
43. Law, M. S.; Wong, K.-Y.; Chan, T. H. Green Chem., 2002, 4, 328.
44. Khadilkar, B. M.; Rebeiro, G. L. Org. Process. Res. Dev., 2002, 6, 826.
45. Deetlefs, M.; Seddon, K. R. Green Chem., 2003, 5, 181.
46. Begg, C. G.; Grimmett, M. R.; Wethey, P. D. Aust. J. Chem., 1973, 26, 2434.
47. Tang, W.; Zhang, X. Chem. Rev., 2003, 103, 3029.
48. Chauvin, Y.; Mussmann, L.; Olivier, H. Angew. Chem. Int. Ed. Engl., 1995, 34, 2698.
49. Dyson, P. J.; Ellis, D. J.; Parker, D. G.; Welton, T. Chem. Commun., 1999, 25.
50. Suarez, P. A. Z.; Dullius, J. E. L.; Einloft, S.; De Souza, R. F.; Dupont, J. Polyhedron, 1996, 7, 1217.
51. Banik, B. K.; Barakat, K. J.; Wagle, D. R.; Manhas, M. S.; Bose, A. K. J. Org. Chem., 1999, 64, 5764.
52. Desai, B.; Danks, T. N. Tetrahedron Lett., 2001, 42, 5963.
53. Berthold, H.; Schotten, T.; Honig, H. Synthesis, 2002, 1607.
54. See for example: a) Grubbs, R. H.; Chang, S. Tetrahedron, 1998, 54, 4413.
55. b) Fürstner, A. Angew. Chem. Int. Ed. Engl., 2000, 39, 3012.
56. Buijsman, R. C.; Van Vuuren, E.; Sterrenburg, J. G. Org. Lett., 2001, 3, 3785.
57. Audic, N.; Clavier, H.; Mauduit, M.; Guillemin, J.-C. J. Am. Chem. Soc., 2003, 125, 9248.
58. Yao, Q.; Zhang, Y. Angew. Chem. Int. Ed., 2003, 42, 3395.
59. Thanh, G. V.; Loupy, A. Tetrahedron Lett., 2003, 44, 9091.
60. Mayo K. G.; Nearhoof, E. H.; Kiddle, J. J. Org. Lett., 2002, 4, 1567.
61. Ferreux, L.; Loupy, A. Tetrahedron, 2001, 55, 9199.
62. Garbacia, S.; Desai, B.; Lavastre, O.; Kappe, C. O. J. Org. Chem., 2003, 68, 9136.
63. See for example: Beletskaya, I.; Cheprakov, A. V. Chem. Rev., 2000, 100, 3009.
64. Jeffery, T. Tetrahedron Lett., 1985, 26, 2667.
65. Herrmann, W. A.; Böhm, V. P. W. J. Organomet. Chem., 1999, 572, 141.
66. Carmichael, A. J.; Earle, M. J.; Holbrey, J. D.; McCormac, P. B.; Seddon, K. R. Org. Lett., 1999, 1, 997.
67. Choudary, B. M.; Madhi, S.; Chowdari, N. S.; Kantam, M. L.; Sreedhar, B. J. Am. Chem. Soc., 2002, 124, 14127.
68. Vallin, K. S. A.; Emilsson, P.; Larhed, M.; Hallberg, A. J. Org. Chem., 2002, 67, 6243.
69. Xie, X.; Lu, J.; Chen, B.; Han, J.; She, X.; Pan, X. Tetrahedron Lett., 2004, 45, 809.
70. Shieh, W.-C.; Lozanov, M. Tetrahedron Lett., 2003, 44, 6943.
71. Delledonne, D.; Rivetti, F.; Romano, U. Applied Catal., 2001, 221, 241.
72. Wegener, G.; Brandt, M.; Duda, L.; Hofmann, J.; Klesczewski, B.; Koch, D.; Kumpf, R.-J.; Orzesek, H.; Pirkl, H.-G.; Six, C.; Steinlein, C.; Weisbeck, M. Applied Catal. A., 2001, 221, 303.
73. Trotzki, R.; Nüchter, M.; Ondruschka, B. Green Chem., 2003, 5, 285.
74. March, J. Advanced Organic Chemistry, John Wiley & Sons, Inc. 1992.
75. a) Bosch, A. I.; de la Cruz, P.; Diez-Parra, E.; Loupy, A.; Langa, F. Synlett, 1995, 1259.
76. b) Thakur, A. J.; Boruah, A.; Prajapati, D.; Sandhu, J. S. Synth. Commun., 2000, 30, 2105.
77. c) Zhou, J.-F.; Tu, S.-J.; Feng, J.-C. Synth. Coummun., 2002, 32, 959.
78. d) Esfghi, H.; Gordi, Z. Synth. Commun., 2003, 33, 2971.
79. Peng, J.; Deng, Y. Tetrahedron Lett., 2001, 42, 403.
80. Ren, R. X.; Zueva, L. D.; Ou, W. Tetrahedron Lett., 2001, 42, 8441.
81. Lee, J. K.; Kim, D.-C.; Song, C. E.; Lee, S.-G. Synth. Commun., 2003, 33, 2301.
82. For review on the cyanation see: a) Ellis, G. A.; Romney-Alexander, T. M. Chem. Rev., 1987, 87, 779.
83. b) Grushin, V. V.; Alper, H. Chem. Rev., 1994, 94, 1047.
84. Wu, J. X.; Beck, B.; Ren, R. X. Tetrahedron Lett., 2002, 43, 387.
85. Leadbeater, N. E.; Torenius, H. M.; Tye, H. Tetrahedron, 2003, 59, 2253.
86. Arvela, R. K.; Leadbeater, N. E. J. Org. Chem., 2003, 68, 9122.
87. Dubreuil, J. F.; Bazureau, J. P. Tetrahedron Lett., 2000, 41, 7351.
88. Fraga-Dubreuil, J.; Bazureau, J. P. Tetrahedron Lett., 2001, 42, 6097.
89. Miao, W.; Chan, T. H. Org. Lett., 2003, 5, 5003.
90. Ren, R. X.; Wu, J. X. Org. Lett., 2001, 3, 3727.
91. Nguyen, H.-P.; Matondo, H.; Baboulene, M. Green Chem., 2003, 5, 303.
92. Ley, S. V.; Leach, A. G.; Storer, R. I. J. Chem. Soc., Perkin Trans. 1, 2001, 358.
93. Leadbeater, N. E.; Torenius, H. M. J. Org. Chem., 2002, 67, 3145.
94. It should be noted that rate acceleration in other Diels-Alder reactions via microwave irradiation has been observed before but the synthetic procedure is often not as convenient as presented here. For examples see Refs 1a and 1b.
95. Hoffmann, J.; Nüchter, M.; Ondruschka, B.; Wassercheid, P. Green Chem., 2003, 5, 296.
96. Lee, C. W. Tetrahedron Lett., 1999, 40, 2461.
97. Song, C. E.; Shim, W. H.; Roh, E. J.; Lee, S.-G.; Choi, J. H. Chem. Commun., 2001, 1122.
98. Kaval, N.; Van der Eycken, J.; Caroen, J.; Dehaen, W.; Strohmeier, G. A.; Kappe, C. O.; Van der Eycken, E. J. Comb. Chem., 2003, 5, 560.
99. Van Der Eycken, E.; Appukkuttan, P.; De Borggraeve, W.; Dehaen, W.; Dallinger, D.; Kappe, C. O. J. Org. Chem., 2002, 67, 7904.
100. For a review in the area see: Weber, L. Med. Chem., 2002, 9, 2085.
101. a) Kappe, C. O., Acc. Chem. Res., 2000, 33, 879.
102. b) Stadler, A.; Kappe, C. O. J. Comb. Chem., 2001, 3, 624.
103. Fraga-Dubreuil, J.; Famelart, M.-H.; Bazureau, J. P. Org. Process Res. Dev., 2002, 6, 374.
104. Fraga- Dubreuil, J.; Bazureau, J. P. Tetrahedron, 2003, 59, 6121.
105. Cox, E. D.; Cook, J. M. Chem. Rev., 1995. 95, 1797.
106. Pal, B.; Jaisankar, P.; Giri, V. S. Synth. Commun., 2003, 33, 2339.
107. Wu, C.-Y.; Sun, C.-M. Synlett., 2002, 10, 1709.
108. Kawate, T.; Yamada, H.; Matsumizu, M.; Nishida, A.; Nakagawa, M. Synlett., 1997, 761.
109. Srinivasan, N.; Ganesan, A. Chem. Commun., 2003, 916.
110. Qian, C.; Huang, T. J. Org. Chem., 1998, 63, 4125.
111. Lee, S.; Lee, J. K.; Song, C. E.; Kim, D. Bull. Korean. Chem. Soc., 2002, 23, 667.
112. Dyatkin A. B.; Rivero, R. A. Tetrahedron Lett., 1998, 39, 3647.
113. McNally J. J.; Youngman, M. A.; Dax, S. L. Tetrahedron Lett., 1998, 39, 967.
114. Wei, C.; Li, Z.; Li, C.-J. Org. Lett., 2003, 5, 4473.
115. Leadbeater, N. E.; Torenius, H. M.; Tye, H. Mol. Divers., 2003, 7, 135.