Flow microwave technology and microreactors in synthesis

Australian Journal of Chemistry

Volumn 66, Issue 2, 2013, Pages 131-144

  Baxendale, Ian R ^a   Hornung, Christian ^b   Ley, Steven V ^c   De Mata Muñoz Molina, Juan ^c   Wikström, Anders ^d  

^a DURHAM UNIVERSITY   (United Kingdom)

^b CSIRO   (Australia)

^c UNIVERSITY OF CAMBRIDGE   (United Kingdom)

^d BIOTAGE AB   (Sweden)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL PROCESS; CHEMICAL TRANSFORMATIONS; CONTINUOUS FLOW REACTION; MICRO REACTOR; MICROWAVE REACTORS; MICROWAVE TECHNOLOGY; REACTION MEDIA; SCALE-UP;

CHEMICAL REACTORS; MICROWAVE DEVICES; ORGANIC CHEMICALS;

SYNTHESIS (CHEMICAL);

EID: 84873920336     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH12365     Document Type: Article

References (59)

1. (a) P. Lidström, J. P. Tierney, B. Wathey, J. Westman, Tetrahedron 2001, 57, 9225. doi:10.1016/S0040-4020(01)00906-1
2. (b) C. O. Kappe, A. Stadler, Microwaves in Organic and Medicinal Chemistry 2005 (Wiley-VCH: Weinheim).
3. (c) J. P. Tierney, P. Lidström (Eds), Microwave-assisted Organic Synthesis 2005lackwell Publishing Ltd: Oxford).
4. (a) V. Hessel, Chem. Eng. Technol. 2009, 32, 1655. doi:10.1002/CEAT. 200900474
5. (b) M. Baumann, I. R. Baxendale, S. V. Ley, Mol. Divers. 2011, 15, 613. doi:10.1007/S11030-010-9282-1
6. (c) A. Sachse, A. Galarneau, B. Coq, F. Fajula, New J. Chem. 2011, 35, 259. doi:10.1039/C0NJ00965B
7. (a) L. F. Raveglia, G. A. M. Giardina, Future Med. Chem. 2009, 1, 1019.
8. (b) W. G. Devine, N. E. Leadbeater, ARKIVOC 2011, V, 127.
9. (c) S. V. Ley, I. R. Baxendale, in Systems Chemistry (Eds M. G. Hicks, C. Kettner) 2009, Proceedings of the Beilstein-Institut Workshop, 26-30 May, 2008, Bozen, Italy, 65-85. Available at http://www. beilsteininstitut.de/Bozen2008/ Proceedings/Ley/Ley.pdf
10. (d) K. Geyer, P. H. Seeberger, in Systems Chemistry (Eds M. G. Hicks, C. Kettner) 2009, Proceedings of the Beilstein-Institut Workshop, 26-30 May, 2008, Bozen, Italy, 87-107. Available at http://www.beilstein-institut.de/Bozen2008/ Proceedings/Seeberger/Seeberger.pdf
11. (e) S. V. Ley, I. R. Baxendale, Chimia 2008, 62, 162. doi:10.2533/CHIMIA.2008.162
12. (a) I. R. Baxendale, M. R. Pitts, Chimica Oggi, Chemistry Today 2006, 24, 241.
13. (b) I. R. Baxendale, J. J. Hayward, S. V. Ley, Comb. Chem. High Throughput Screen. 2007, 10, 802. doi:10.2174/138620707783220374
14. (c) T. N. Glasnov, C. O. Kappe, Macromol. Rapid Commun. 2007, 28, 395. doi:10.1002/MARC.200600665
15. (d) J. R. Schmink, C. M. Kormos,W. G. Devine, N. E. Leadbeater, Org. Process Res. Dev. 2010, 14, 205. doi:10.1021/OP900287J
16. (e) T. N. Glasnov, C. O. Kappe, Chem.-Eur. J. 2011, 17, 11956. doi:10.1002/CHEM.201102065
17. (a) S. Saaby, I. R. Baxendale, S. V. Ley, Org. Biomol. Chem. 2005, 3, 3365. doi:10.1039/B509540A
18. (b) I. R. Baxendale, J. Deeley, C. M. Griffiths-Jones, S. V. Ley, S. Saaby, G. K. Tranmer, Chem.-Eur. J. 2006, 12, 4407. doi:10.1002/CHEM.200501400
19. (c) C. J. Smith, J. Iglesias-Sigüenza, I. R. Baxendale, S. V. Ley, Org. Biomol. Chem. 2007, 5, 2758. doi:10.1039/B709043A
20. (d) J. Sedelmeier, S. V. Ley, H. Lange, I. R. Baxendale, Eur. J. Org. Chem. 2009, 4412. doi:10.1002/EJOC.200900344
21. M. C. Bagley, R. L. Jenkins, M. C. Lubinu, C. Mason, R. Wood, J. Org. Chem. 2005, 70, 7003. doi:10.1021/JO0510235
22. A. Debache, R. Boulcina, A. Belfaitah, S. Rhouati, B. Carboni, Synlett 2008, 2008, 509. doi:10.1055/S-2008-1032093
23. http://www.uniqsis.com/paProductsDetail.aspx?ID1/2ACC-MIX for details on the baffled mixer chip (verified September 2012).
24. (a) H. R. Sahoo, J. G. Kralj, K. F. Jensen, Angew. Chem. Int. Ed. 2007, 46, 5704. doi:10.1002/ANIE.200701434
25. (b) J. Wiss, C. Fleury, C. Heuberger, U. Onken, M. Glor, Org. Process Res. Dev. 2007, 11, 1096. doi:10.1021/OP7000645
26. (c) K. Yamatsugu, S. Kamijo, Y. Suto, M. Kanai, M. Shibasaki, Tetrahedron Lett. 2007, 48, 1403. doi:10.1016/J.TETLET.2006. 12.093
27. (d) H. Lebel, O. Leogane, Org. Lett. 2006, 8, 5717. doi:10.1021/OL0622920
28. (e) M. Baumann, I. R. Baxendale, S. V. Ley, N. Nikbin, C. D. Smith, J. P. Tierney, Org. Biomol.Chem. 2008, 6, 1577. doi:10.1039/B801631N (f)M.Baumann, I. R.Baxendale, S.V. Ley,N.Nikbin,C.D. Smith, Org. Biomol. Chem. 2008, 6, 1587. doi:10.1039/B801634H
29. (a) V. Singh, S. Kaur, V. Sapehiyi, J. Singh, G. L. Kad, Catal. Commun. 2005, 6, 57. doi:10.1016/J.CATCOM.2004.10.011
30. (b) M. S. Manhas, S. N. Ganguly, S. Mukherjee, A. K. Jain, A. K. Bose, Tetrahedron Lett. 2006, 47, 2423. doi:10.1016/J.TETLET. 2006.01.147
31. (c) B. Tyagi, M. K. Mishra, R. V. Jasra, J. Mol. Catal. A-Chem. 2007, 276, 47. doi:10.1016/J.MOLCATA.2007.06.003
32. (d) Y. Reddy, S. Thirupathi, S. Vijayakumar, P. Crooks, P. Dasari, P. Reddy, P. Narsimha, B. Rajitha, Synthetic Commun. 2008, 38, 2082. doi:10.1080/00397910802029091
33. (e) A. Sinhamahapatra, N. Sutradhar, S. Pahari, H. C. Bajaj, A. B. Panda, Appl. Catal. A-Gen. 2011, 394, 93. doi:10.1016/J.APCATA. 2010.12.027
34. Q. Zhang, S. Zhang, Y. Deng, Green Chem. 2011, 13, 2619. doi:10.1039/C1GC15334J
35. (g) J. Zak, D. Ron, E. Riva, H. P. Harding, B. C. S. Cross, I. R. Baxendale, Chem.-Eur. J. 2012, 18, 9901. doi:10.1002/CHEM. 201201039
36. (a) S. V. Ley, A. G. Leach, R. I. Storer, J. Chem. Soc., Perkin Trans. 1 2001, 358. doi:10.1039/B008814P
37. (b) R. Mart?́nez-Palou, J. Mex. Chem. Soc. 2007, 51, 252.
38. (c) N. E. Leadbeater, H. M. Torenius, in Microwaves in Organic Synthesis (Ed. A. Loupy) 2008, Ch. 7, pp. 327-361 (Wiley-VCH: Weinheim).
39. Weflon is Milestone's proprietary microwave absorbing carbonmpregnated Teflon material; Si/C, see: D. Obermayer, B. Gutmann, C. O. Kappe, Angew. Chem. Int. Ed. 2009, 48, 8321. doi:10.1002/ANIE.200904185
40. (a) G. E. Keck, J. B. Yates, J. Am. Chem. Soc. 1982, 104, 5829. doi:10.1021/JA00385A066
41. (b) S. D. Burke, W. F. Fobare, D. M. Armistead, J. Org. Chem. 1982, 47, 3348. doi:10.1021/JO00138A037
42. (c) F. Le Guyader, B. Quiclet-Sire, S. Seguin, S. Z. Zard, J. Am. Chem. Soc. 1997, 119, 7410. doi:10.1021/JA9708878
43. P.-J. Shim, H.-D. Kim, Tetrahedron Lett. 1998, 39, 9517. doi:10.1016/S0040-4039(98)02228-X
44. (a) T. L. Mindt, R. Schibli, J. Org. Chem. 2007, 72, 10247. doi:10.1021/JO702030E
45. (b) H. Harkat, A. Y. Dembelé, J.-M. Weibel, A. Blanc, P. Pale, Tetrahedron 2009, 65, 1871. doi:10.1016/J.TET.2008.10.112
46. (c) J. Alemán, V. del Solar, L. Cubo, A. G. Quiroga, C. N. Ranninger, Dalton Trans. 2010, 10601. doi:10.1039/C0DT00506A
47. G. Sun, C. Cheng, K. L. Wooley, Macromolecules 2007, 40, 793. doi:10.1021/MA062592X
48. C. R. Sarko, in Microwave-assisted Organic Synthesis (Eds J. P. Tierney, P. Lidström) 2005, Ch. 8, pp. 222-236lackwell Publishing Ltd: Oxford).
49. (b) B. L. Hayes, Microwave Synthesis: Chemistry at the Speed of Light 2002 (CEM Publishing: Matthews, NC).
50. J. Habermann, S. V. Ley, J. S. Scott, J. Chem. Soc., Perkin Trans. 1 1999, 10, 1253. doi:10.1039/A901802F
51. (a) P. F. Schuda, W. A. Price, J. Org. Chem. 1987, 52, 1972. doi:10.1021/JO00386A014
52. (b) I. R. Baxendale, A.-L. Lee, S. V. Ley, J. Chem. Soc., Perkin Trans. 1 2002, 1850. doi:10.1039/B203388G
53. (a) A. S. Zentiva, H. Stepankova, P. Pihera, J. Hajicek, A Method of Preparation of Ramipril, WO patent, 121084, 2005.
54. (b) V. Teetz, R. Geiger, H. Baul, Tetrahedron Lett. 1984, 25, 4479. doi:10.1016/S0040-4039(01)81471-4
55. (c) M. Baumann, I. R. Baxendale, S. V. Ley, N. Nikbin, Beilstein J. Org. Chem. 2011, 7, 442. doi:10.3762/BJOC.7.57
56. H. Urbach, X. Uenning, Tetrahedron 1985, 26, 1839. doi:10.1016/S0040- 4039(00)94751-8
57. Continuous Flow Catalytic Reactions with FlowCAT. Available at http://www.helgroup.com/reactor-systems/hydrogenation-catalysis/ flowcat-highpressure-flowchemistry-in-a-compact-unit/
58. J. M. Hawkins, Trickle Bed Flow Hydrogenation Using Shallow Beds of Fine Catalyst Particles: Enhanced Diastereoselectivity, Purity Control, and Catalyst Activity Relative to Batch Hydrogenations, Abstracts of Papers, 242nd ACS National Meeting & Exposition, Denver, CO, United States, 28 August-1 September 2011.
59. Glass beads acid-washed; 212-300 mm available from Sigma-Aldrich cat. no. G1277 and 150-212 mm available from Sigma-Aldrich cat. no. G1145.