Microwave-assisted organic synthesis in near-critical water at 300°C - A proof-of-concept study

European Journal of Organic Chemistry

Volumn , Issue 17, 2005, Pages 3672-3679

  Kremsner, Jennifer M ^a   Kappe, C Oliver ^a  

^a UNIVERSITY OF GRAZ   (Austria)

Author keywords

Green chemistry; High temperature chemistry; Microwaves; Water chemistry

Indexed keywords

EID: 25144451808     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/ejoc.200500324     Document Type: Article

References (79)

1. C.-J. Li, T.-H. Chan, Organic Reactions in Aqueous Media, Wiley, New York, NY, 1997.
2. a) R. Breslow, Acc. Chem. Res. 1991, 24, 159-164;
3. b) P. A. Grieco, Aldrichim. Acta 1991, 24, 59-66;
4. c) C.-J. Li, Chem. Rev. 1993, 93, 2023-2035.
5. U. M. Lindström, Chem. Rev. 2002, 102, 2751-2772.
6. W. Blokzijl, J. B. F. N. Engberts, Angew. Chem. Int. Ed. Engl. 1993, 32, 1545-1579.
7. B. Widom, P. Bhimalapuram, K. Koga, Phys. Chem. Chem. Phys. 2003, 5, 3085-3093.
8. a) P. Krammer, H. Vogel, J. Supercrit. Fluids 2000, 16, 189-206;
9. b) P. Krammer, S. Mittelstädt, H. Vogel, Chem. Eng. Technol. 1999, 22, 126-130.
10. a) D. Bröll, C. Kaul, A. Krämer, P. Krammer, T. Richter, M. Jung, H. Vogel, P. Zehner, Angew. Chem. 1999, 111, 3180-3196;
11. b) P. E. Savage, Chem. Rev. 1999, 99, 603-621;
12. c) M. Siskin, A. R. Katritzky, Chem. Rev. 2001, 101, 825-836;
13. d) A. R. Katritzky, D. A. Nichols, M. Siskin, R. Murugan, M. Balasubramanian, Chem. Rev. 2001, 101, 837-892;
14. e) N. Akiya, P. E. Savage, Chem. Rev. 2002, 102, 2725-2750;
15. f) H. Weingärtner, E. U. Franck, Angew. Chem. Int. Ed. 2005, 44, 2672-2692.
16. a) S. Minett, K. Fenwick, L. Stenmark, Spec. Chem. Mag. 2001, 21, 30-32;
17. b) X.-H. Qi, Y.-Y. Zhuang, Y.-C. Yuan, W.-X. Gu, J. Hazard. Mater. 2002, 90, 51-62;
18. c) G. Del Re, G. Di Giacomo, Desalination 2001, 138, 61-64;
19. d) S. Baur, H. Schmidt, A. Kraemer, J. Gerber, J. Supercrit. Fluids 2005, 33, 149-157.
20. R. Gedye, F. Smith, K. Westaway, H. Ali, L. Baldisera, L. Laberge, J. Rousell, Tetrahedron Lett. 1986, 27, 279-282.
21. R. J. Giguere, T. L. Bray, S. M. Duncan, G. Majetich, Tetrahedron Lett. 1986, 27, 4945-4948.
22. Review: C. O. Kappe, Angew. Chem. Int. Ed. 2004, 43, 6250-6284;
23. Books: a) A. Loupy, Microwaves in Organic Synthesis, Wiley-VCH, Weinheim, 2002;
24. b) P. Lidstöm, J. P. Tierney, Microwave-Assisted Organic Synthesis, Blackwell Scientific, 2005;
25. c) C. O. Kappe, A. Stadler, Microwaves in Organic and Medicinal Chemistry, Wiley-VCH, Weinheim, 2005.
26. a) A. de la Hoz, A. Diaz-Ortiz, A. Moreno, Chem. Soc. Rev. 2005, 34, 164-178;
27. b) L. Perreux, A. Loupy, Tetrahedron 2001, 57, 9199-9223;
28. c) N. Kuhnert, Angew. Chem. Int. Ed. 2002, 41, 1863-1866;
29. d) C. Strauss, Angew. Chem. Int. Ed. 2002, 41, 3589-3590.
30. a) V. Molteni, M. M. Hamilton, L. Mao, C. M. Crane, A. P. Termin, D. M. Wilson, Synthesis 2002, 1669-1674;
31. b) P. S. Baran, D. P. O'Malley, A. L. Zografos, Angew. Chem. Int. Ed. 2004, 43, 2674-2677;
32. c) N. E. Leadbeater, M. Marco, J. Org. Chem. 2003, 68, 888-892;
33. d) L. Bai, J.-X. Wang, Y. Zhang, Green Chem. 2003, 5, 615-617;
34. e) J.-X. Wang, Z. Liu, Y. Hu, B. Wei, L. Bin, Synth. Commun. 2002, 32, 1607-1614;
35. f) N. E. Leadbeater, M. Marco, B. J. Tominack, Org. Lett. 2003, 5, 3919-3922;
36. g) . P. Appukkuttan, W. Dehaen, E. Van der Eycken, Eur. J. Org. Chem. 2003, 4713-4716;
37. h) N. Kaval, K. Bisztray, W. Dehaen, C. O. Kappe, E. Van der Eycken, Mol. Diversity 2003, 7, 125-133;
38. i) R. K. Arvela, N. E. Leadbeater, H. M. Torenius, H. Tye, Org. Biomol. Chem. 2003, 1, 1119-1121;
39. j) D. Villemin, M. J. Gomez-Escalonilla, J.-F. Saint-Clair, Tetrahedron Lett. 2001, 42, 635-637;
40. k) T. A. Bryson, J. J. Stewart, J. M. Gibson, P. S. Thomas, J. K. Berch, Green Chem. 2003, 5, 174-176;
41. l) T. A. Bryson, J. M. Gibson, J. J. Stewart, H. Voegtle, A. Tiwari, J. H. Dawson, W. Marley, B. Harmon, Green Chem. 2003, 5, 177-180;
42. m) R. K. Arvela, N. E. Leadbeater, M. S. Sangi, V. A. Williams, P. Granados, R. D. Singer, J. Org. Chem. 2005, 70, 161-168.
43. [33,34] for details.
44. [11,16] for more details.
45. B. Hayes, Microwave Synthesis, CEM Publishing, Matthews, NW, 2002.
46. E. Neas, M. Collins, Introduction to Microwave Sample Preparation: Theory and Practice (Eds.: H. M. Kingston, L. B. Jassie), American Chemical Society, Washington, DC, 1988.
47. a) C. Gabriel, S. Gabriel, E. H. Grant, B. S. Halstead, D. M. P. Mingos, Chem. Soc. Rev. 1998, 27, 213-224;
48. b) D. M. P. Mingos, D. R. Baghurst, Chem. Soc. Rev. 1991, 20, 1-47.
49. N. E. Leadbeater, S. J. Pillsbury, E. Shanahan, V. A. Williams, Tetrahedron 2005, 61, 3565-3585.
50. L. A. Torry, R. Kaminsky, M. T. Klein, M. R. Klotz, J. Supercrit. Fluids 1992, 5, 163-168.
51. H. P. Lesutis, R. Gläser, C. L. Liotta, C. A. Eckert, Chem. Commun. 1999, 20, 2063-2064.
52. A. R. Katritzky, A. R. Lapucha, Energy Fuels 1990, 4, 555-561.
53. A. Krämer, S. Mittelstädt, H. Vogel, Chem. Eng. Technol. 1998, 21, 494-500.
54. a) A. Stadler, S. Pichler, G. Horeis, C. O. Kappe, Tetrahedron 2002, 58, 3177-3183;
55. b) G. Horeis, S. Pichler, A. Stadler, W. Gössler, C. O. Kappe. Fifth International Electronic Conference on Synthetic Organic Chemistry (ECSOC-5), September 1-30, 2001, http://www.mdpi.net/ecsoc-5/e0000/e0000.htm.
56. A. R. Katritzky, F. J. Luxem, M. Siskin, Energy Fuels 1990, 4, 518-524.
57. J. An, L. Bagnell, T. Cablewski, C. R. Strauss, R. W. Trainor, J. Org. Chem. 1997, 62, 2505-2511.
58. a) K. S. Jerome, E. J. Parsons, Organometallics 1993, 12, 2991-2993;
59. b) E. Mizushima, K. Sato, T. Hayashi, M. Tanaka, Angew. Chem. Int. Ed. 2002, 41, 4563-4565.
60. A. Vasudevan, M. K. Verzal, Synlett 2004, 631-634.
61. D. L. Hughes, Org. Prep. Proced. Int. 1993, 25, 609-632.
62. H. M. Hugel, D. J. Kennaway, Org. Prep. Proced. Int. 1995, 27, 1-31.
63. J. T. Fitzpatrick, R. D. Hiser, J. Org. Chem. 1957, 22, 1703-1704.
64. B. Robinson, The Fischer Indole Synthesis, Wiley, Chichester, 1982, pp. 642-653.
65. a) C. R. Strauss, R. W. Trainor, Aust. J. Chem. 1995, 48, 1665-1692;
66. b) C. R. Strauss, Aust. J. Chem. 1999, 52, 83-96.
67. K. D. Raner, C. R. Strauss, R. W. Trainor, J. S. Thorn, J. Org. Chem. 1995, 60, 2456-2460.
68. J. Boeseken, W. R. Van Tonningen, Recl. Trav. Chim. Pays-Bas 1920, 39, 187-190.
69. a) Y. Ikushima, K. Hatakeda, O. Sato, T. Yokoyama, M. Arai, Angew. Chem. Int. Ed. 1999, 38, 2910-2914;
70. b) Y. Ikushima, K. Hatakeda, O. Sato, T. Yokoyama, M. Arai, J. Am. Chem. Soc. 2000, 122, 1908-1918.
71. B. Kuhlmann, E. M. Arnett, M. Siskin, J. Org. Chem. 1994, 59, 3098-3101.
72. U. Pindur, G. Lutz, G. Otto, Chem. Rev. 1993, 93, 741-761.
73. M. B. Korzenski, J. W. Kolis, Tetrahedron Lett. 1997, 38, 5611-5614.
74. Y. Harano, H. Sato, F. Hirata, J. Am. Chem. Soc. 2000, 122, 2289-2293.
75. A. Stadler, B. H. Yousefi, D. Dallinger, P. Walla, E. van der Eycken, N. Kaval, C. O. Kappe, Org. Process Res. Dev. 2003, 7, 707-716.
76. C. J. Salomon, E. G. Mata, O. A. Mascaretti, J. Org. Chem. 1994, 59, 7259-7266.
77. M. Behforouz, J. L. Bolan, M. S. Flynt, J. Org. Chem. 1985, 50, 1186-1189.
78. M. Akazome, T. Kondo, Y. Watanabe, J. Org. Chem. 1994, 59, 3375-3380.
79. J. B. Lambert, D. E. Marko, J. Am. Chem. Soc. 1985, 107, 7978-7982.