Microwave reactions under continuous flow conditions

Combinatorial Chemistry and High Throughput Screening

Volumn 10, Issue 10, 2007, Pages 802-836

  Baxendale, Ian R ^a   Hayward, John J ^a   Ley, Steven V ^a  

^a Department of Chemistry   (United Kingdom)

Author keywords

Flow; Mesoreactor; Microreactor; Microwave; Process intensification; Reactor; Scale up

Indexed keywords

LINALOOL; PHENETOLE; POLITEF;

BATCH REACTOR; BENZYLATION; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMBINATORIAL CHEMISTRY; CONTINUOUS FLOW REACTOR; CYCLIZATION; DEVICE; DIELECTRIC CONSTANT; ESTERIFICATION; FRIEDEL CRAFTS REACTION; HEAT EXCHANGE; HEATING; HYDROLYSIS; MATHEMATICAL COMPUTING; MICROWAVE IRRADIATION; ORGANIC CHEMISTRY; PRIORITY JOURNAL; RACEMIZATION; REVIEW; SUBSTITUTION REACTION; SYNTHESIS; TECHNOLOGY;

CHEMISTRY, ORGANIC; COMBINATORIAL CHEMISTRY TECHNIQUES; EQUIPMENT DESIGN; HEATING; MICROWAVES; MODELS, CHEMICAL; ULTRASONICS;

EID: 40849116347     PISSN: 13862073     EISSN: None     Source Type: Journal    
DOI: 10.2174/138620707783220374     Document Type: Review

References (137)

1. a) Mehdizadeh, M. Res. Chem. Intermed., 1994, 20, 79.
2. b) Schwalbe, T.; Simons, K. Chem. Today, 2006, 24, 56.
3. a) Baghursy, D.R.; Mingos, D.M.P. Chem. Soc. Rev., 1991, 20, 1.
4. b) Gabriel, C.; Gabriel, S.; Grant, E.H.; Halstead, B.S.; Mingos, D.M.P. Chem. Soc. Rev., 1998, 27, 213.
5. c) Kingston, H.M.; Haswell, S.J. Microwave-Enhanced Chemistry. Fundementals, Sample Preparation and Applications, ACS: Washington D.C., 1997.
6. d) Gedye, R.; Smith, F.; Westway, K.; Ali, H.; Baldisera, L.; Laberge, L.; Rusell, J. Tetrahedron Lett., 1986, 27, 279.
7. e) Larhed, M.; Olofsson, K. Microwave Methods in Organic Synthesis, Springer: Berlin 2006.
8. nd Ed, Wiley-VCH: Weinheim 2006.
9. Maxwell, J.C. A Treatise on Electricity and Magnetism, Clarendon Press: Oxford, 1873.
10. a) Metaxas, A.C.; Meredith, R.J. Industrial Microwave Heating, Peregrinus, 1998.
11. b) Lidström, P.; Tieney, J.; Wathey, B.; Westman, J. Tetrahedron, 2001, 57, 9225.
12. c) Mingos, D.M.P.; Baghurst, D.R. In Microwave Enhanced Chemistry; Kingston, H.M.; Haswell, S.J. Eds; ACS: Washington, DC 1997, pp 3-54.
13. d) Majetich, G.; Wheless, K. In Microwave Enhanced Chemistry; Kingston, H.M.; Haswell, S.J. Eds; ACS: Washington, DC 1997, pp 455-506.
14. Barringer, S.A.; Davis, E.A.; Gordon, J.; Ayappa, K.G.; Davis H.T. AIChE J.l, 1994, 40, 1433.
15. Clark, D.E.; Sutton, W.H. Annu. Rev. Mater. Sci., 1996, 26, 299.
16. a) http://www.pueschner.com/basics/eindringtiefe_en.php.
17. b) Bogdal D. Microwave-assisted organic synthesis. One hundred reaction procedures. Elsevier: Oxford, 2005.
18. c) Craig, D.Q.M. Dielectric Aspects of Pharmacological Systems, Talyor and Francis: London, 1995.
19. Meredith, R.J. Power & Energy Engineers' Handbook of Industrial Microwave Heating, Institution of Electrical Engineers: Stevenage, 1998.
20. a) Nüchter, M.; Ondruschka, B. Mol. Divers., 2003, 7, 253.
21. b) Howarth, P.; Lockwood, M. Chem. Eng., 2004, 756, 29.
22. c) Baxendale, I.R.; Pitts, M.R. Chem. Today, 2006, 24, 41.
23. rd Microwave Power Symposium, Chicago, IL July 11-15. 1998, 63.
24. d) Glasnov, T.N.; Kappe, C.O. Macromolecular Rapid Communications, 2007, 28, 395.
25. e) Wolkenburg, S.E.; Shipe, W.D.; Lindsay, C.W.; Guare, P.J.; Pawluczyk J.M. Curr. Opin. Drug Disc. Dev., 2005, 8, 701.
26. a) Strauss, C.R. Chem. Aust., 1990, 186.
27. b) Chen, S.-T.; Chiou, S.-H.; Wang K.-T. J. Chem. Soc. Chem. Commun., 1990, 807.
28. a) Gedye, R; Smith, F.; Westway, K.; Ali, H.; Baldisera, L.; Laberge, L.; Rousell, J. Tetrahedron Lett., 1986, 27, 279.
29. b) Giguere, R.J.; Bray, T.L.; Duncan, S.M.; Majetich, G. Tetrahedron Lett., 1986, 27, 4945.
30. Nüchter, M.; Ondruschka, B.; Bonrath, W.; Gum, A. Green Chem., 2004, 6, 128.
31. a) Cablewski, T.; Faux, A.F.; Strauss, C.R. J. Org. Chem., 1994, 59, 3408.
32. b) Roberts, B.A.; Strauss, C.R. Acc. Chem. Res., 2005, 38, 653.
33. Bagnell, T.; Bliese, M.; Cablewski, T.; Strauss, C.R.; Tsanaktsidis, J. Aust. J. Chem., 1997, 50, 921.
34. Chen, S.-T.; Chiou, S.-H.; Wang, K.-T. J. Chin. Chem. Soc., 1991, 38, 85.
35. a) McGill, S.L.; Walkiewicz, J.W. J. Microwave Power Electromag. Energy, 1987, 22, 175.
36. b) Cameron, K.L.; Depew, M.C.; Wan, J.K.S. Res. Chem. Intermed., 1991, 16, 221.
37. c) Wan, J.K.S.; Tse, M.Y.; Husby, H.; Depew, M.C. J. Microwave Power Electromag. Energy, 1990, 25, 32.
38. Wan, J.K.S.; Bamwenda, G.; Depew, M.C., Res. Chem. Intermed., 1991, 16, 241.
39. Zhang, X.; Lee, C.S.-M.; Mingos, D.M.P.; Hayward, D.O. Cat. Lett., 2003, 88, 129.
40. a) Zhang, X.L.; Hayward, D.O.; Mingos, D.M.P. Chem. Commun., 1999, 975.
41. b) Zhang, X.L.; Hayward, D.O.; Lee, C.; Mingos, D.M.P. Appl. Catal. B-Environ., 2001, 33, 137.
42. a) Koch, T.A.; Krause, K.R.; Mehdizadeh, M. Process Safety Prog., 1997, 16, 241.
43. b) Wan, J.K.S.; Koch, T.A. Res. Chem. Intermed., 1994, 20, 29.
44. c) USPatent US/6287531.
45. d) World Patent WO/1995/021126.
46. a) Chemat, F.; Poux, M.; di Martino, J.-L.; Berlan, J. Chem. Eng. Technol., 1996, 19, 420.
47. b) Chemat, F.; Esveld, D.C.; Poux, M.; di Martino, J.-L. J. Microwave Power and Electromagnetic Energy, 1998, 33, 88.
48. Kabza, K.G.; Chapados, B.R.; Gestwicki, J.E.; McGrath, J.L. J. Org Chem., 2000, 65, 1210.
49. Pipus, G.; Plazl, I.; Koloini, T. Chem. Eng. J., 2000, 76, 239.
50. Cáceres, A.; Jaimes, M.; Chávez, G.; Bravo, B.; Ysambertt, F.; Márquez, N. Talanta, 2005, 68, 359.
51. Shieh, W.-C.; Dell, S.; Repič, O. Tetrahedron Lett., 2002, 43, 5607.
52. http://www.milestonesrl.com
53. Shieh, W.-C.; Lozanov M.; Repič O. Tetrahedron Lett., 2003, 44, 6943.
54. Shieh, W.-C.; Dell, S.; Repič, O. Org. Lett., 2001, 3, 4279.
55. a) Ondruschka, B.; Nüchter, M. In Advances in Microwave and Radio Frequency Processing; Willert-Porada, M. Ed.; Springer: Berlin, 2006; pp 390-397.
56. b) Nüchter, M.; Ondruschka, B.; Bonrath, W.; Gum, A. Green Chem., 2004, 6, 128.
57. c) Bierbaum, R.; Nüchter, M.; Ondruschka, B. Chem. Ing. Technol., 2004, 76, 961.
58. French Patent 2833260
59. a) Esveld, E.; Chemat, F.; van Haveren, J. Chem. Eng. Technol., 2005, 23, 429.
60. b) Esveld, E.; Chemat, F.; van haveren, J. Chem. Eng. Technol., 2000, 23, 279.
61. a) Bram, G.; Loupy, A. In Preparative Chemistry using supported reagents, Laszlo, P. Ed.; Academic Press: New York, 1987; p 387-400.
62. b) Hayes, B.L. Microwave Synthesis; Chemistry at the speed of light. CEM Publishing: Bloomington, IN; 2002.
63. a) Lehmann, F.; Pilotti, Å, Luthman, K. Mol. Divers., 2003, 7, 145.
64. b) Sarko, C.R. In Microwave Assisted Organic Synthesis Tierney, J.P.; Lidström, P., Eds; Blackwell Publishing: Oxford, 2005, pp 222-236 and references therein.
65. c) Borman S. Chem. Eng. News, 2001, 79, 49-58.
66. Lehmann, H.; LaVecchia, L. J. Assoc. Lab. Autom., 2005, 10, 412.
67. www.biotage.com
68. www.anton-parr.com
69. www.cemsynthesis.com
70. Ley, S. V.; Baxendale, I. R.; Bream, R. N.; Jackson, P. S.; Leach, A. G.; Longbottom, D. A.; Nesi, M.; Scott, J. S.; Storer, R. I.; Taylor, S. J. J. Chem Soc. Perkin Trans. 1, 2000, 3815 and references therein.
71. Loones, K.T.J.; Maes, B.U.W.; Rombouts, G.; Hostyn, S.; Diels G. Tetrahedron, 2005, 61, 10338.
72. I. R. Baxendale, unpublished results.
73. Dye, J.L.; Lok, M.T.; Tehan, F.J.; Creaso, J.M.; Voorhees, K.J. J. Org. Chem., 1973, 38, 1773.
74. a) Jähnisch, K.; Hessel, V.; Löwe, H.; Baerns, M. Angew. Chem. Int. Ed., 2004, 43, 406.
75. b) Fletcher, P.D.I.; Haswell, S.J.; Pombo-Villar, E.; Warrington, B.H.; Watts, P.; Wong, S.Y.F.; Zhang, X. Tetrahedron, 2002, 58, 4735.
76. c) Pennemann, H.; Watts, P.; Haswell, S.J.; Hessel, V.; Löwe, H. Org. Process Res. Dev., 2004, 8, 422.
77. d) Taghavi-Moghadam, S.; Kleemann, A.; Golbig, K.G. Org. Process Res. Dev., 2001, 5, 652.
78. e) Jas, G.; Kirschning, A. Chem. Eur. J., 2003, 9, 5708.
79. f) Smith, C.D.; Baxendale, I.R.; Tranmer, G.K.; Baumann, M.; Smith, S.C.; Lewthwaite R.A.; Ley, S.V. Org. Biomol. Chem., 2007, 1562.
80. g) Ley S.V.; Baxendale, I.R. Nat. Rev. Drug Discov., 2002, 1, 573.
81. h) Hodge, P. Ind. Eng. Chem. Res., 2005, 44, 8542.
82. i) Ley, S.V.; Baxendale, I.R.; Myers, R.M. In Comprehensive Medicinal Chemistry II, Taylor, J.B.; Triggle, D.J. Eds; Elsevier: Oxford, 2006, Vol. 3, pp 791-839.
83. j) Hornung, C.H.; Mackley, M.R.; Baxendale, I.R.; Ley, S.V. Org. Proc. Res. Dev., 2007, 399.
84. k) Chemical Micro Process Engineering, Processing and Plants, Hessel, V.; Löwe, H.; Müller, A.; Kolb, G., Eds; Wiley-VCH: Weinheim, 2005.
85. l) Microreactors, New Technology for Modern Chemistry, Ehrfield, W.; Hessel V.; Löwe, H., Eds; Wiley-VCH: Weinheim, 2000.
86. m) Baxendale, I.R.; Griffiths-Jones, C.M.; Ley S.V.; Tranmer, G.K. Synlett, 2006, 427.
87. n) Baxendale, I.R.; Deely, J.; Griffiths-Jones, C.M.; Ley, S.V.; Saaby, S.; Tranmer, G.K. Chem. Commun., 2006, 2566.
88. o) Baxendale, I.R.; Ley, S.V.; Smith, C.D.; Tranmer, G.K. Chem. Commun., 2006, 4835.
89. p) Baumann, M.; Baxendale, I.R.; Ley, S.V.; Smith, C.D.; Tranmer, G.K. Org. Lett., 2006, 8, 5231.
90. q) Luckarift, H.R.; Nadeau, L.J.; Spain, J.C. Chem. Commun., 2005, 383.
91. r) Lee, C.K.Y.; Holmes, A.B.; Ley, S.V.; McConvey, I.F.; Al-Duri, B.; Leeke, G.A.; Santos, R.C.D.; Seville, J.P.K. Chem. Commun., 2005, 2175.
92. s) Hafez, A.M.; Taggi, A.E.; Lectka, T. Chem. Eur. J., 2002, 8, 4114.
93. t) Hafez, A.M.; Taggi, A.E.; Wack, H.; Drury, W.J.; Lectka, T. Org. Lett., 2000, 2, 3963.
94. u) Doku, G.N.; Verboom, W.; Reinhoudt D.N.; van den Berg, A. Tetrahedron, 2005, 61, 2733.
95. Marquié, J.; Salmoria, G.; Poux, M.; Laporterie, A.; Dubac, J.; Roques, N., Ind. Eng. Chem. Res., 2001, 40, 4485.
96. a) Khadilkar, B.M.; Madyar, V.R. Org. Proc. Res. Dev., 2001, 5, 452.
97. th International Electronic Conference on Synthetic Organic Chemistry (ECSOC-5), 2001.
98. Bagley, M.C.; Jenkins, R.L.; Lubinu, M.C.; Mason, C.; Wood, R. J. Org. Chem., 2005, 70, 7003.
99. Glasnov, T.N.; Vugts, D.J.; Koningstein, M.M.; Desai, B.; Fabian, W.M.F.; Orru, R.V.A.; Kappe, C.O. QSAR Comb. Sci., 2006, 25, 509.
100. Wilson, N.S.; Sarko, C.R.; Roth, G.P. Org. Proc. Res. Dev., 2004, 8, 535.
101. Bonnet, C.; Estel, L.; Ledoux, A.; Mazari, B.; Louis, A. Chem. Eng. Proc., 2004, 43, 1435.
102. a) De la Hoz, A.; Díaz-Ortiz, Á.; Moreno, A. Chem. Soc. Rev., 2005, 34, 1640.
103. b) Habermann, J.; Ponzi, S.; Ley, S.V. Mini Reviews in Org. Chem., 2005, 2, 125.
104. Pillai, U.R.; Sahle-Demessie, E.; Varma, R.S. Green Chem. 2004, 6, 295.
105. Arvela, R.K.; Leadbeater, N.E.; Collins Jr., M.J. Tetrahedron, 2005, 61, 9349.
106. Jachuck, R.J.J.; Selvaraj, D.K.; Varma, R.S. Green Chem., 2006, 8, 29.
107. Baxendale, I.R.; Griffiths-Jones, C.M.; Ley, S.V.; Tranmer, G.K. Chem. Eur. J., 2006, 12, 4407.
108. a) Chemat, F.; Poux, M.; DiMartino, J.L.; Berlan, J. J. Microwave Power Electromagn. Energy, 1996, 31, 19.
109. b) Chemat, F.; Poux, M.; Galema, S.A. J. Chem. Soc. Perkin Trans. 2, 1997, 2371.
110. c) Strier, C.P.; Luche, J.L. In Synthetic Organic Sonochemistry, Luche, J.-L. Ed.; Plenum Press: New York, 1998; pp. 53-57.
111. d) Peng, Y.; Song, G. Green Chem., 2001, 3, 302.
112. e) Peng, Y.; Song, G. Green Chem. 2002, 4, 349.
113. f) Peng, Y.; Song, G. Green Chem., 2003, 5, 704.
114. g) Peng, Y.; Dou, R.; Song, G.; Jiang, J. Synlett, 2005, 2245.
115. Cravotto, G.; Cintas, P. Chem. Eur. J., 2007, 13, 1902.
116. Cravotto, G.; Beggiato, M.; Penoni, A.; Palmisano, G.; Tollari, S.; Lévêque, J.-M.; Bonrath, W. Tetrahedron Lett., 2005, 46, 2267.
117. a) Saaby, S.; Baxendale, I. R.; Ley, S. V. Org. Biomol. Chem., 2005, 3, 3365.
118. b) Baxendale, I.R.; Ley, S.V. In Ernst Schering Foundation Symposium Proceedings - Enabling Technologies, Springer-Verlag: Berlin Heidelberg, 2007.
119. Wilson, N.S.; Sarko, C.R.; Roth, G.P. Org. Proc. Res. Dev., 2004, 8, 535.
120. Savin, K.A.; Robertson, M.; Gernert, D.; Green, S.; Hembre, E.J.; Bishop J. Mol. Divers., 2003, 7, 171.
121. Strauss, C.R.; Trainor, R.W. Aust. J. Chem., 1995, 48, 1665.
122. Pitts, M.R.; McCormack, P.; Whittall, J. Tetrahedron, 2006, 62, 4705.
123. a) Weber, L. Drug Discov. Today, 2002, 7, 143.
124. b) Hulme, C.; Gore, V. Curr. Med. Chem. 2003,10, 51.
125. c) Tietze, L.F.; Modi, A. Med. Res. Rev., 2000, 20, 304.
126. d) Bienaymé, H.; Hulme, C.; Oddon, G.; Schmitt, P. Chem. Eur. J., 2000, 6, 3321.
127. Bremner, W.S.; Organ, M.G. J. Comb. Chem., 2007, 9, 14.
128. Smith, C.J.; Iglesias-Sigüenza, J.; Baxendale, I.R.; Ley, S.V. Org. Biomol. Chem., 2007, in press. DOI: 10.1039/b709043a.
129. He, P.; Haswell, S.J.; Fletcher, P.D.I. LabChip, 2004, 4, 38.
130. He, P.; Haswell, S.J.; Fletcher, P.D.I. Appl. Cat. A. Gen., 2004, 274, 111.
131. He, P.; Haswell, S.J.; Fletcher, P.D.I. Sensors and Actuators B, 2005, 105, 516.
132. Comer, E.; Organ, M.G. J. Am. Chem. Soc., 2005, 127, 8160.
133. Shore, G.; Morin, S.; Organ, M.G. Angew. Chem. Int. Ed., 2006, 45, 2761.
134. Comer, E.; Organ, M.G. Chem. Eur. J., 2005, 11, 7223.
135. Rodríguez-Clemente, R.; Gómez-Morles, J. J. Crystal Growth, 1996, 169, 339-346.
136. Bonamartini, A.; Bondioli, F.; Ferrari, A.M.; Focher, B.; Leonelli, C. Powder Technol., 2006, 167, 45.
137. Braun, I.; Schulz-Ekloff, G.; Wöhrle, D.; Lautenschläger, W. Micropor. Mesopor. Mater., 1998, 23, 79.