The combined use of microwaves and ultrasound: Improved tools in process chemistry and organic synthesis

Chemistry - A European Journal

Volumn 13, Issue 7, 2007, Pages 1902-1909

  Cravotto, Giancarlo ^a   Cintas, Pedro ^b  

^a UNIVERSITY OF TURIN   (Italy)

^b UNIVERSITY OF EXTREMADURA   (Spain)

Author keywords

Flow reactors; Green chemistry; Microwaves; Synthetic methods; Ultrasound

Indexed keywords

MICROWAVE HEATING; QUANTUM THEORY; SYNTHESIS (CHEMICAL); ULTRASONIC DEVICES; ULTRASONIC WAVES;

FLOW REACTORS; GREEN CHEMISTRY; SYNTHETIC METHODS; TANDEM IRRADIATION;

MICROWAVE DEVICES;

CATALYSIS; EQUIPMENT DESIGN; INSTRUMENTATION; METHODOLOGY; MICROWAVE RADIATION; ORGANIC CHEMISTRY; REVIEW; ULTRASOUND;

CATALYSIS; CHEMISTRY, ORGANIC; EQUIPMENT DESIGN; MICROWAVES; ULTRASONICS;

EID: 34250653146     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.200601845     Document Type: Article

References (46)

1. P. Kündig. Science 2006, 314, 430-431.
2. a) T. Y. Zhang, Chem. Rev. 2006, 106, 2583-2595;
3. b) A. E. Rubin, S. Tummala, D. A. Both, C. Wang, E. J. Delaney, Chem. Rev. 2006, 106, 2794-2810.
4. a) Microwaves in Organic Synthesis (Ed.: A. Loupy), Wiley-VCH, Weinheim, 2006;
5. b) Microwaves in Organic and Medicinal Chemistry (Eds.: C. O. Kappe, A. Stadler), Wiley-VCH, Weinheim, 2005.
6. T. J. Mason, J. Lorimer, Applied Sonochemistry: Uses of Power Ultrasound in Chemistry and Processing, Wiley-VCH, Weinheim, 2002.
7. C.O. Kappe, Angew. Chem. 2004, 116, 6408-6443;
8. Angew. Chem. Int. Ed. 2004, 43, 6250-6284.
9. L. Perreux. A. Loupy, Tetrahedron 2001, 57, 9199-9223.
10. K. S. Suslick, L. A. Crum, in Encyclopedia of Acoustics (Ed.: M. J. Cracker). Wiley, New York, 1997, pp. 271-282.
11. a) G. Cravotto, P. Cintas, Chem. Soc. Rev. 2006, 35, 180-196;
12. b) T. Mason, P. Cintas, in Handbook of Green Chemistry and Technology (Eds.: J. Clark. D. Macquarric), Blackwell, Oxford, 2002, pp. 372-396.
13. a) C.-G. Chen, P.-J. Hong, S.-H. Dai, J.-D. Ran, J. Chem. Soc. Faraday Trans. 1995, 91, 1179-1180;
14. b) X. L. Zhang, D.O. Hayward, D. M. P. Mingos. Chem. Commun. 1999, 975-976.
15. For discussion of safety issues: a) C. R. Strauss, R. W. Trainor. Aust. J. Chem. 1995, 48. 1665-1692;
16. b) H. M. Kingston, L. B. Jassie, in Introduction to Microwave Sample Preparation (Eds.: H. M. Kingston, L. B. Jassie). American Chemical Society, Washington, DC, 1998, pp. 231-233.
17. T. J. Mason. Practical Sonochemistry. User's Guide to Applications in Chemistry and Chemical Engineering, Ellis Horwood, London, 1991, pp. 32-36.
18. C. Buffa, G. Cravotto, G. Omiccioli Patent TO A-000766, 2006.
19. a) F. Chemat, M. Poux, J. L. Di Martino, J. Berlan, J. Microwave Power Electromagn. Eneregy 1996, 31, 19-22;
20. b) F. Chemat, M. Poux, S. A. Galema. J. Chem. Soc. Perkin Trans. 2 1997, 2371-2374.
21. Correlations between the solvent properties and the cavitation energy are complex: as a general rule, the rates of sonochemical reactions can be increased by lowering the vapor pressure of the solvent. The presence of vaporized liquid in the bubbles makes the cavitational collapse less energetic: C. Pétrier, J.-L. Luche, in Synthetic Organic Sonochemistrv (Ed.: J.-L. Luche), Plenum Press, New York, 1998. pp. 53-57.
22. Y. Peng, G. Song, Green Chem. 2001, 3, 302-304.
23. Y. Peng, G. Song, Green Chem. 2002, 4, 349-351.
24. Y. Peng, G. Song, Green Chem. 2003, 5, 704-706.
25. Y. Peng, R. Dou, G. Song, J. Jiang, Synlett 2005, 2245-2247.
26. Common hydrotropes include ureas, alcohols, amino acids, and sugars. A series of particular solute-solute interactions in aqueous solvents have been identified: J. B. F. N. Engherts, M. J. Blandamer, J. Phys. Org. Chem. 1998, 11, 841-846.
27. B. Toukoniitty, J. P. Mikkola, D. Y. Murzin, T. Salmi, Appl. Catal. A 2005, 279, 1-22.
28. G. Cravotto, M. Beggiato, A. Penoni, G. Palmisano, S. Tollari, J.-M. Levêque, W. Bonrath, Tetrahedron Lett. 2005, 46, 2267-2271.
29. a) N. E. Leadbeater, M. Marco. Org. Lett. 2002, 4, 2973-2976;
30. b) L. Bai, J.-X. Wang, Y. Zhang, Green Chem. 2003, 5, 615-617: reports on MW-assisted Suzuki couplings without Pd catalysts;
31. c) N. E. Leadbeater, M. Marco. Angew. Chem. 2003, 115, 1445-1447;
32. Angew. Chem. Int. Ed. 2003, 42, 1407-1409;
33. d) N. E. Leadbeater, M. Marco, J. Org. Chem. 2003, 68, 5660-5667;
34. these last results have been reassessed arguing that Pd contaminants, even on the ppb scale, found in commercially available sodium carbonate are responsible for the formation of biaryls rather than a Pd-frec pathway: R. K. Arvela, N. E. Leadbeater, M. S. Sangi, V. A. Williams. P. Granados, R. D. Singer, J. Org. Chem. 2005, 70, 161-168.
35. G. Cravotto, G. Palmisano, S. Tollari, G. M. Nano, A. Penoni, Ultrason. Sonochem. 2005, 12, 91-94.
36. G. Cravotto, L. Boffa, M. Bia, W. Bonrath, M. Curini, G. A. Heropoulos, Synlett 2006, 2605-2608.
37. R. Self, Extraction of Organic Analytes from Foods. A Manual of Methods, Royal Society, Cambridge. 2005.
38. G. Cravotto. P. Cintas, in Modifying Flavour in Food (Eds.: A. Taylor, J. Hort), Woodhead, Cambridge, 2006. Chapt. 4.
39. L. Zhao, G. Zhao, F. Chen, Z. Wang, J. Wu, X. Hu, J. Agric. Food Chem. 2006, 54, 8346-8351.
40. A. Lagha, S. Chemat, P. V. Bartels, F. Chemat, Analusis 1999, 27, 452-457.
41. S. Chemat, A. Lagha, H. A. Amar, F. Chemat, Ultraxon. Sonochem. 2004, 11, 5-8.
42. See for instance: a) W. Bonrath. Ultrason. Sonochem. 2004. 11. 1-4;
43. b) V. Roy, L. Colombeau, R. Zcrrouki, P. Krausz, Carbohytir. Rex. 2004, 339, 1829-1831;
44. c) G. Cravotto, L. Boffa, M. Turello, M. Parenti, A. Barge, Steroids 2005, 70, 77-83.
45. For a recent revision: J.-M. Levêque, G. Cravotto. Chimia 2006, 60, 313-320.
46. K. Geyer, J. D. C. Codée, P. H. Seeberger. Chem. Eur. J. 2006. 12, 8434-8442.