Microwave-assisted synthesis under continuous-flow conditions

Macromolecular Rapid Communications

Volumn 28, Issue 4, 2007, Pages 395-410

  Glasnov, Toma N ^a   Kappe, C Oliver ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

Batch reactors; Continuous flow; Microwave heating; Processing; Synthesis

Indexed keywords

BATCH REACTORS; SYNTHESIS (CHEMICAL);

CONTINUOUS FLOW PROCESSING; STOP FLOW PROCESSING;

MICROWAVE HEATING;

EID: 34447108082     PISSN: 10221336     EISSN: 15213927     Source Type: Journal    
DOI: 10.1002/marc.200600665     Document Type: Review

References (90)

1. H. M. Kingston, S. J. Haswell, "Microwave-Enhanced Chemistry. Fundamentals, Sample Preparation and Applications", American Chemical Society, Washington 1997.
2. [2a] R. Gedye, F. Smith, K. Westway, H. Ali, L. Baldisera, L Laberge, J. Rusell, Tetrahedron Lett. 1986, 27, 279;
3. [2b] R. J. Giguere, T. L. Bray, S. M. Duncan, G. Majetich, Tetrahedron Lett. 1986, 27, 4945;
4. [2c] R. N. Gedye, F. E. Smith, K. C Westway, Can. J. Chem. 1988, 66, 17.
5. st edition, Wiley-VCH, Weinheim 2002;
6. [3b] B. L Hayes, "Microwave Synthesis: Chemistry at the Speed of Light" CEM Publishing, Matthews, NC 2002;
7. [3c] P. Lidström, J. P. Tierney, "Microwave-Assisted Organic Synthesis", Blackwell Publishing, Oxford 2005;
8. [3d] C. O. Kappe, A. Stadler, "Microwaves in Organic and Medicinal Chemistry", Wiley-VCH, Weinheim 2005;
9. nd edition, Wiley-VCH, Weinheim 2006;
10. [3f] M. Larhed, K. Olofsson, "Microwave Methods in Organic Synthesis", Springer, Berlin 2006.
11. [4a] C. O. Kappe, Angew. Chem. Int. Ed. 2004, 43, 6250;
12. [4b] B. L. Hayes, Aldrichim. Acta 2004, 37, 66;
13. [4c] M. Nüchter, B. Ondruschka, W. Bonrath, A. Gun, Green Chem. 2004, 6, 128;
14. [4d] B. A. Roberts, C. R. Strauss, Acc. Chem. Res. 2005, 38, 653.
15. [5a] A. De La Hoz, A. Diaz-Ortiz, A. Moreno, Chem. Soc. Rev. 2005, 34, 164;
16. [5b] L. Perreux, A. Loupy, Tetrahedron 2001, 57, 9199;
17. [5c] N. Kuhnert, Angew. Chem. Int. Ed. 2002, 41, 1863;
18. [5d] C. R. Strauss, Angew. Chem. Int. Ed. 2002, 41, 3589.
19. [6a] D. Bogdal, P. Penczek, J. Pielichowski, A. Prociak, Adv. Polym. Sci. 2003, 163, 193;
20. [6b] F. Wiesbrock, R. Hoogenboom, U. S. Schubert, Macromol. Rapid Commun. 2004, 25, 1739.
21. [7a] M. Larhed, A. Hallberg, Drug Discovery Today 2001, 6, 406;
22. [7b] B. Wathey, J. Tierney, P. Lidström, J. Westman, Drug Discovery Today 2002, 7, 373;
23. [7c] F. Al-Obeidi, R. E. Austin, J. F. Okonya, D. R. S. Bond, Mini-Rev. Med. Chem. 2003, 3, 449;
24. [7d] W. D. Snipe, S. E. Wolkenberg, C. W. Lindsley, Drug Discovery Today: Technol. 2005, 2, 155;
25. [7e] C. O. Kappe, D. Dallinger, Nat. Rev. Drug Discovery 2006, 5, 51.
26. [8a] S. Barlow, S. R. Marder, Adv. Fund. Mater. 2003, 13, 517;
27. [8b] Y.-J. Zhu, W. W. Wang, R.-J. Qi, X.-L. Hu, Angew. Chem. Int. Ed. 2004, 43, 1410.
28. M. Tsuji, M. Hashimoto, Y. Nishizawa, M. Kubokawa, T. Tsuji, Chem. Eur. J. 2005, 11, 440.
29. [10a] K. Orrling, P. Nilsson, M. Gullberg, M. Larhed, Chem. Commun. 2004, 790;
30. [10b] H. Zhong, Y. Zhang, Z. Wen, L. Li, Nat. Biotechnol. 2004, 22, 1291;
31. [10c] H. Zhong, S. L. Marcus, L. Li, J. Am. Soc. Mass Spectrom. 2005, 16, 471.
32. [11a] C. Gabriel, S. Gabriel, E. H. Grant, B. S. Halstead, D. M. P. Mingos, Chem. Soc. Rev. 1998, 27, 213;
33. [11b] D. M. P. Mingos, D. R. Baghurst, Chem. Soc. Rev. 1991, 20, 1.
34. J. M. Kremsner, A. Stadler, C. O. Kappe, Topics Curr. Chem. 2006, 266, 233.
35. [13a] C. R. Strauss, R. W. Trainor, Aust. J. Chem. 1995, 48, 1665;
36. [13b] C R. Strauss, Aust. J. Chem. 1999, 52, 83;
37. nd edition, A. Loupy, Ed., Wiley-VCH, Weinheim 2006, Vol. 1, p. 109.
38. For a recent review on continuous flow organic chemistry, see: G. Jas, A. Kirschning, Chem. Eur. J. 2003, 9, 5708.
39. A. Kirschning, W. Solodenko, K. Mennecke, Chem. Eur. J. 2006, 12, 5972.
40. [16a] WO 90/03840 (1990), Commonwealth Scientific and Industrial Research Organization, invs.: C. R. Strauss, A. F. Faux. For other patents in the field of microwave flow instrumentation, see: [
41. 16b] WO 02/102116 (2002), Forschungszentrum Karlsruhe GMBH, invs.: L. Feher, H. Baumgärtner, G. Link;
42. [16c] WO 03/041856 (2003), Personal Chemistry, Uppsala AB, invs.: M. Fagrell;
43. [16d] US 05/133498 A1 (2005), CEM Corporation, invs.: M. J. Collins, M. J. Collins, Jr., W. P. Hargett, Jr., E. E. King, G. W. Busse;
44. [16e] WO 05/099891 A3 (2005), CEM Corporation, invs.: M. J. Collins, Jr., W. P. Hargett, Jr., E. E. King, J. J. Lambert, J. M. Thomas.
45. For recent publications highlighting microwave applications under flow conditions, see: [17a] T. Schwalbe, K. Simons, Chem. Today 2006, 24, 56;
46. [17b] I. R. Baxendale, M. Pitts, Chem. Today 2006, 24, 41.
47. [18a] K. Jähnisch, V. Hessel, H. Löwe, M. Baerns, Angew. Chem. Int. Ed. 2004, 43, 406;
48. [18b] P. D. I. Fletcher, S. J. Haswell, E. Pombo-Villar, B. H. Warrington, P. Watts, S. Y. F. Wong, X. Zhang, Tetrahedron 2002, 58, 4735;
49. [18c] H. Pennemann, P. Watts, S. J. Haswell, V. Hessel, H. Löwe, Org. Process Res. Dev. 2004, 8, 422;
50. [18d] S. Taghavi-Moghadam, A. Kleemann, K. G. Golbig, Org. Process Res. Dev. 2001, 5, 652;
51. [18e] W. Ehrfeld, V. Hessel, H. Löwe, "Microreactors: New Technology for Modern Chemistry", Wiley-VCH, Weinheim 2000.
52. [19a] P. He, S. J. Haswell, P. D. Fletcher, Lab Chip 2004, 4, 38;
53. [19b] P. He, S. J. Haswell, P. D. Fletcher, Appl. Catal. A 2004, 274, 111;
54. [19c] P. He, S. J. Haswell, P. D. Fletcher, Sen. Actuators, B 2005, 105, 516.
55. For a literature survey on commercially available microwave reactors, see ref. [3d] (Chapter 3) and [3e] (Chapter 2). See also the following websites: [20a] Anton Paar GmbH: http://www.anton-paar.com;[20b] Biotage AB: http://www.biotage.com;[20c] CEM Corporation: http://www.cem.com;[20d] Milestone s.r.l. : http://www.milestonesci.com.
56. R. J. J. Jachuck, D. K. Selvaraj, R. S. Varma, Green Chem. 2006, 8, 29.
57. [22a] E. Comer, M. G. Organ, J. Am. Chem. Soc. 2005, 127, 8160;
58. [22b] G. Shore, S. Morin, M. G. Organ, Angew. Chem. Int. Ed. 2006, 45, 2761;
59. [22c] E. Comer, M. G. Organ, Chem. Eur. J. 2005, 11, 7223.
60. [23a] U. Kunz, A. Kirschning, H.-L. Wen, W. Solodenko, R. Cecilia, C. O. Kappe, T. Turek, Catal. Today 2005, 105, 318;
61. [23b] K. Mennecke, R. Cecilia, T. N. Glasnov, S. Gruhl, C. Vogt, A. Feldhoff, M. A. L Vargas, C. O. Kappe, U. Kunz, A. Kirschning, unpublished results.
62. N. S. Wilson, C. R. Sarko, G. Roth, Org. Process. Res. Dev. 2004, 8, 535.
63. S. Saaby, I. R. Baxendale, S. V. Ley, Org. Biomol. Chem. 2005, 3, 3365.
64. I. R. Baxendale, C. M. Griffiths-Jones, S. V. Ley, G. K. Tranmer, Chem. Eur. J. 2006, 12, 4407.
65. [27a] R. K. Arvela, N. E. Leadbeater, Org. Lett. 2005, 7, 2101;
66. [27b] B. K. Singh, P. Appukkuttan, S. Claerhout, V. S. Parmar, E. Van der Eycken, Org. Lett. 2006, 8, 1863.
67. K. A. Savin, M. Robertson, D. Gernert, S. Green, E. J. Hembre, J. Bishop, Mol. Diversity 2003, 7, 171.
68. M. C. Bagley, R. L. Lenkins, M. C. Lubinu, C. Mason, R. Wood, J. Org. Chem. 2005, 70, 7003.
69. T. N. Glasnov, D. J. Vugts, M. M. Koningstein, B. Desai, W. M. F. Fabian, R. V. A. Orru, C. O. Kappe, QSAR Comb. Sci. 2006, 26, 509.
70. U. R. Pillai, E. Sahle-Demessie, R. S. Varma, Green Chem. 2004, 6, 295.
71. R. K. Arvela, N. E. Leadbeater, M. J. Collins, Jr., Tetrahedron 2005, 61, 9349.
72. K. T. J. Loones, B. U. W. Maes, G. Rombouts, S. Hostyn, G. Diels, Tetrahedron 2005, 61, 10338.
73. M. R. Pitts, P. McCormack, J. Whittall, Tetrahedron 2006, 62, 4705.
74. S. T. Chen, S. H. Chiou, K. T. Wang, J. Chem. Soc. Chem. Commun. 1990, 807.
75. T. Cablewski, A. F. Faux, C. R. Strauss, J. Org. Chem. 1994, 59, 3408.
76. F. Chemat, M. Poux, J.-L. di Martino, J. Berlan, Chem. Eng. Technol. 1996, 19, 420.
77. [38a] I. Plazi, G. Pipus, T. Koloini, AIChE 1997, 43, 754;
78. [38b] G. Pipus, I. Plazi, T. Koloini, Chem. Eng. J. 2000, 76, 239.
79. K. Kazba, B. R. Chapados, J. E. Gestwicki, J. L. McGrath, J. Org. Chem. 2000, 65, 1210.
80. B. M. Khadlikar, V. R. Madyar, Org. Process. Res. Dev. 2001, 5, 452.
81. J. Marquie, G. Salmoriea, M. Poux, A. Laporterie, J. Dubac, N. Roques, Ind. Eng. Chem. Res. 2001, 40, 4485.
82. [42a] W. C Shieh, S. Dell, O. Repič, Org. Lett. 2001, 3, 4279;
83. [42b] W. C. Shieh, S. Dell, O. Repič, Tetrahedron Lett. 2002, 43, 5607;
84. [42c] W. C. Shieh, M. Lozanov, O. Repič, Tetrahedron Lett. 2003, 44, 6943.
85. I. Braun, G. Schulz-Ekloff, D. Wöhrle, W. Lautenschläger, Micropor. Mesopor. Mater. 1998, 23, 79.
86. [44a] E. Esveld, F. Chemat, J. van Haveren, Chem. Eng. Technol. 2000, 23, 279;
87. [44b] E. Esveld, F. Chemat, J. van Haveren, Chem. Eng. Technol 2000, 23, 429.
88. [45a] M. Nüchter, B. Ondruschka, Mol. Diversity 2003, 7, 253;
89. [45b] R. Bierbaum, M. Nüchter, B. Ondruschka, Chem. Ing. Technol. 2004, 76, 961.
90. P. Howarth, M. Lockwood, "The Chemical Engineer", 2004, 756, 29; for further information see: http://www.sairem.com.