Microwave-assisted coupling reactions in aqueous media

RSC Green Chemistry

Volumn , Issue , 2010, Pages 55-90

  Fihri, Aziz ^a   Len, Christophe ^a  

^a UNIVERSITÉ DE TECHNOLOGIE DE COMPIÈGNE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84897477077     PISSN: 17577039     EISSN: 17577047     Source Type: Book Series    
DOI: 10.1039/9781849730990-00055     Document Type: Article

References (101)

1. V. V. Grushin and H. Alper, in Activation of Unreactive Bonds and Organic Synthesis, ed. S. Murai, Springer, Berlin, 1999, pp. 193-226
2. V. Polshettiwar, C. Len and A. Fihri, Coord. Chem. Rev., 2009, 253, 2599-2626
3. L. Yin and J. Liebscher, Chem. Rev., 2007, 107, 133-173
4. V. Polshettiwar and R. S. Varma, Chem. Soc. Rev., 2008, 37, 1546-1557
5. D. Dallinger and C. O. Kappe, Chem. Rev., 2007, 107, 2563-2591
6. N. Miyaura, T. Yanagi and A. Suzuki, Synth. Commun., 1981, 11, 513-519
7. N. Miyaura and A. Suzuki, Chem. Rev., 1995, 95, 2457-2483
8. N. Miyaura, Cross-Coupling Reactions: A Practical Guide, Springer, New York, 2002
9. M. Larhed and A. Hallberg, J. Org. Chem., 1996, 61, 9582-9584
10. M. Larhed, G. Lindeberg and A. Hallberg, Tetrahedron Lett., 1996, 37, 8219-8222
11. N. E. Leadbeater and M. Marco, Org. Lett., 2002, 4, 2973-2976.
12. N. E. Leadbeater and M. Marco, J. Org. Chem., 2003, 68, 888-892
13. A. F. Littke and G. C. Fu, Angew. Chem. Int. Ed., 2002, 41, 4176-4211
14. G. Miao, P. Ye, L. Yu and C. M. Baldino, J. Org. Chem., 2005, 70, 2332-2334
15. R. K. Arvela and N. E. Leadbeater, Org. Lett., 2005, 7, 2101-2104
16. K. W. Anderson and S. L. Buchwald, Angew. Chem. Int. Ed., 2005, 44, 6173-6177
17. P. Čapek, R. Pohl and M. Hocek, Org. Biomol. Chem., 2006, 4, 2278-2284
18. P. Čapek, M. Vrábel, Z. Hasník, R. Pohl and M. Hocek, Synthesis, 2006, 3515-3526
19. R. B. Bedford, C. P. Butts, T. E. Hurst and P. Lidström, Adv. Synth. Catal., 2004, 346, 1627-1630
20. I. D. Kostas, G. A. Heropoulos, D. Kovala-Demertzi, P. N. Yadav, J. P. Jasinski, M. A. Demertzis, F. J. Andreadaki, G. Vo-Thanh, A. Petit and A. Loupy, Tetrahedron Lett., 2006, 47, 4403-4407
21. X. Mei, Rhia M. Martin and C. Wolf, J. Org. Chem., 2006, 71, 2854-2861
22. G. Cravotto, M. Beggiato, A. Penoni, G. Palmisano, S. Tollari, J.-M. Lévêque and W. Bonrath, Tetrahedron Lett., 2005, 46, 2267-2271
23. M. Nishimura, M. Ueda and N.Miyaura, Tetrahedron, 2002, 58, 5779-5787
24. A. Konovets, A. Penciu, E. Framery, N. Percina, C. Goux-Henry and D. Sinou, Tetrahedron Lett., 2005, 46, 3205-3208
25. E. J. García Suarez, A. Ruiz, S. Castilló n, W. Oberhauser, C. Bianchini and C. Claver, Dalton Trans., 2007, 285-2861
26. R. Lépine and J. Zhu, Org. Lett., 2005, 7, 2981-2984
27. J. Wannberg, Y. A. Sabnis, L. Vrang, B. Samuelsson, A. Karlén, A. Hallberg and M. Larhed, Bioorg. Med. Chem., 2006, 14, 5303-5315
28. P. Appukkuttan, W. Dehaen and E. Van der Eycken, Org. Lett., 2005, 7, 2723-2726
29. P. Appukkuttan, W. Dehaen and E. Van der Eycken, Chem. Eur. J., 2007, 13, 6452-6460
30. P. Appukkuttan, A. B. Orts, R. P. Chandran, J. L. Goeman, J. Van der Eycken, W. Dehaen and E. Van der Eycken, Eur. J. Org. Chem., 2004, 3277-3285
31. M. D. Crozet, C. Castera-Ducros and P. Vanelle, Tetrahedron Lett., 2006, 47, 7061-7065
32. J. V. Metzger, in Thiazole and its Derivatives, John Wiley & Sons, Inc., New York, 1979
33. A. A. Kiryanov, P. Sampson and A. J. Seed, J. Org. Chem., 2001, 66, 7925-7929
34. T. Bach and S. Heuser, Tetrahedron Lett., 2000, 41, 1707-1710
35. A. Cohen, M. D. Crozet, P. Rathelot and P. Vanelle, Green Chem., 2009, 11, 1736-1742
36. E. De Clercq, Nat. Rev. Drug Discovery, 2002, 1, 13-25
37. E. De Clercq, Antiviral Res., 2005, 67, 56-75
38. R. Zhu, F. Qu, G. Quéléver and L. Peng, Tetrahedron Lett., 2007, 48, 2389-2393.
39. Y. Gong, J. K. Barbay, A. B. Dyatkin, T. A. Miskowski, E. S. Kimball, S. M. Prouty, M. C. Fisher, R. J. Santulli, C. R. Schneider, N. H. Wallace, S. A. Ballentine, W. E. Hageman, J. A. Masucci, B. E. Maryanoff, B. P. Damiano, P. Andrade-Gordon, D. J. Hlasta, P. J. Hornby and W. He, J. Med. Chem., 2006, 49, 3402-3411
40. R. K. Arvela, N. E. Leadbeater, T. L. Mack and C. M. Kormos, Tetrahedron Lett., 2006, 47, 217-220
41. R. L. Harker and R. D. Crouch, Synthesis, 2007, 1, 25-27
42. G. W. Kabalka, L. Li Zhou and A. Naravane, Tetrahedron Lett., 2006, 47, 6887-6889
43. L. Baia and J.-X. Wanga, Adv. Synth. Catal., 2008, 350, 315-320
44. F.-X. Felpin, T. Ayad and S. Mitra, Eur. J. Org. Chem., 2006, 2679-2690
45. N. T. S. Phan, M. Van Der Sluys and C. W. Jones, Adv. Synth. Catal., 2006, 348, 609-679
46. W. Solodenko, U. Schö n, J. Messinger, A. Glinschert and A. Kirschning, Synlett, 2004, 1699-1702
47. K. M. Dawood, Tetrahedron, 2007, 63, 9642-9651
48. S.-S. Yi, D.-H. Lee, E. Sin and Y.-S. Lee, Tetrahedron Lett., 2007, 48, 6771-6775
49. J. Ku Cho, R. Najman, T. W. Dean, O. Ichihara, C. Muller and M. Bradley, J. Am. Chem. Soc., 2006, 128, 6276-6277
50. C. G. Blettner, W. A. König, W. Stenzel and T. Schotten, J. Org. Chem., 1999, 64, 3885-3890
51. W. Zhang, C. Hiu-Tung Chen, Y. Lu and T. Nagashima, Org. Lett., 2004, 6, 1473-1476
52. A. M. Trzeciak and J. J. Ziolkowski, Coord. Chem. Rev., 2005, 249, 2308-2322
53. T. Mizoroki, K. Mori and A. Ozaki, Bull. Chem. Soc. Jpn., 1971, 44, 581
54. R. F. Heck and J. P. Nolly, J. Org. Chem., 1972, 37, 2320-2322
55. A. Eisenstadt and D. J. Ager, in Fine Chemicals through Heterogeneous Catalysis, ed. R. A. Sheldon and H. van Bekkum, Wiley-VCH, Verlag GmbH, Weinheim, 2001, p. 576
56. A. Zapf and M. Beller, Top. Catal., 2002, 19, 101-109
57. J.-X. Wang, Z. Liu, Y. Hu, B. Wei and L. Bai, Synth. Commun., 2002, 32, 1607-1614
58. R. K. Arvela and N. E. Leadbeater, J. Org. Chem., 2005, 70, 1786-1790
59. R. K. Arvela, S. Pasquini and M. Larhed, J. Org. Chem., 2007, 72, 6390-6396
60. J. Gil-Moltó , S. Karlström and C. Nájera, Tetrahedron, 2005, 61, 12168-12176
61. K. M. Dawood, W. Solodenko and A. Kirschning, ARKIVOC, 2007 (5) 104-124
62. D. E. Bergbreiter and S. Furyk, Green Chem., 2004, 6, 280-285
63. C. Nájera and L. Botella, Tetrahedron, 2005, 61, 9688-9695.
64. M. Zhu, Y. Song and Y. Cao, Synthesis, 2007, 6, 853-856.
65. I. Paterson, R. D. Davies and R. Marquez, Angew. Chem., Int. Ed., 2001, 40, 603-607
66. M. Toyota, C. Komori and M. Ihara, J. Org. Chem., 2000, 65, 7110-7113
67. K. C. Nicolaou and W.-M. Dai, Angew. Chem., Int Ed. Engl., 1991, 30, 1387-1416
68. R. Wu, J. S. Schumm, D. L. Pearson and J. M. Tour, J. Org. Chem., 1996, 61, 6906-6921
69. U. H. F. Bunz, Chem. Rev., 2000, 100, 1605-1644
70. K. Sonogashira, Y. Tohda and N. Hagihara, Tetrahedron Lett., 1975, 16, 4467-4470
71. M. Erdé lyi and A. Gogoll, J. Org. Chem., 2001, 66, 4165-4169
72. G. W. Kabalka, L. Wang, V. Namboodiri and R. M. Pagni, Tetrahedron Lett., 2000, 41, 5151-5154.
73. J. Li, A. W.-H. Mau and C. R. Strauss, Chem. Commun., 1997, 1275-1276
74. N. E. Leadbeater,M. Marco and B. J. Tominack, Org. Lett., 2003, 5, 3919- 3922
75. P. Appukkuttan, W. Dehaen and E. van der Eycken, Eur. J. Org. Chem., 2003, 4713-4716
76. R. K. Arvela, N. E. Leadbeater, M. Sangi, V. Williams, P. Granados and R. D. Singer, J. Org. Chem., 2005, 70, 161-168
77. A. J. McCarroll, T. D. Bradshaw, A. D. Westwell, C. S. Matthews and M. F. G. Stevens, J. Med. Chem., 2007, 50, 1707-1710
78. D. Milstein and J. K. Stille, J. Am. Chem. Soc., 1978, 100, 3636-3638
79. J. K. Stille, Angew. Chem. Int. Ed. Engl., 1986, 25, 508-524
80. P. Espinet and A. M. Echavarren, Angew. Chem. Int. Ed., 2004, 43, 4704- 4734
81. N. Kaval, K. Bisztray, W. Dehaen, C. O. Kappe and E. Van der Eycken, Mol. Diversity, 2003, 7, 125-133
82. T. Hiyama and Y. Hatanaka, Pure Appl. Chem., 1994, 66, 1471-1478
83. T. Hiyama, inMetal-Catalyzed Cross-Coupling Reactions, ed. F. Diederich, P.J. Stang, Wiley-VCH, New York, 1998, ch 10
84. C. J. Handy, A. S. Manoso, W. T. McElroy, W. M. Seganish and P. DeShong, Tetrahedron, 2005, 61, 12201-12225
85. T. Huang and C.-J. Li, Tetrahedron Lett., 2002, 43, 403-405
86. C. Wolf and R. Lerebours, Org. Lett., 2004, 6, 1147
87. E. Alacid and C. Ná jera, Adv. Synth. Catal., 2006, 348, 2085-2091
88. D. E. Uehling, S. S. Nanthakumar, D. Croom, D. L. Emerson, P. P. Leitner, M. J. Luzzio, G. McIntyre, B. Morton, S. Profeta, J. Sisco, D. D. Sternbach, W.-Q. Tong, A. Vuong and J. M. Besterman, J. Med. Chem., 1995, 38, 1106-1118
89. K. Friedrich and K. Wallenfels, in The Chemistry of the Cyano Group, Z. Rappoport (ed.), Interscience, London, 1970, p 67
90. G. A. Ellis and T. M. Romney-Alexander, Chem. Rev., 1987, 87, 779-794
91. M. Alterman and A. Hallberg, J. Org. Chem., 2000, 65, 7984-7989.
92. R. K. Arvela, N. E. Leadbeater, H. M. Torenius and H. Tye, Org. Biomol. Chem., 2003, 1, 1119-1121
93. S. Velmathi and N. E. Leadbeater, Tetrahedron Lett., 2008, 49, 4693-4694
94. Applied Homogeneous Catalysis with Organometallic Compounds: A Comprehensive Handbook in Three Volumes, 2nd, Completely Revised and Enlarged Edition, ed. B. Cornils and W. A. Herrmann, Wiley-VCH, 2002
95. N.-F. K. Kaiser, A. Hallberg and M. Larhed, J. Comb. Chem., 2002, 4, 109-111
96. J. Georgsson, A. Hallberg and M. Larhed, J. Comb. Chem., 2003, 5, 350- 352
97. X. Wu and M. Larhed, Org. Lett., 2005, 7, 3327-3329
98. W. A. Herrmann, V. P. W. Böhm and C.-P. Reisinger, J. Organomet. Chem., 1999, 576, 23-41
99. X. Wu, J. K. Ekegren and M. Larhed, Organometallics, 2006, 25, 1434- 1439
100. G. Lesma, A. Sacchetti and A. Silvani, Synthesis, 2006, 594-596
101. C. M. Kormos and N. E. Leadbeater, Synlett, 2006, 1663-1666.