Metal-catalyzed reactions in water under MW irradiation

RSC Green Chemistry

Volumn , Issue , 2010, Pages 10-54

  Cadierno, Victorio ^a   Crochet, Pascale ^a   García Garrido, Sergio E ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 84897473383     PISSN: 17577039     EISSN: 17577047     Source Type: Book Series    
DOI: 10.1039/9781849730990-00010     Document Type: Article

References (142)

1. A. S. Matlack, Introduction to Green Chemistry, Marcel Dekker, New York, 2001
2. M. Lancaster, Green Chemistry: An Introductory Text, Royal Society of Chemistry, Cambridge, 2002
3. P. T. Anastas and M. M. Kirchhoff, Acc. Chem. Res., 2002, 35, 686
4. U. M. Lindström, Chem. Rev., 2002, 102, 2751
5. C.-J. Li, Chem. Rev., 2005, 105, 3095
6. Organic Reactions in Water: Principles, Strategies and Applications, ed. U. M. Lindstro? m, Blackwell, Oxford, 2007
7. C. I. Herreri'as, X. Yao, Z. Li and C. J. Li, Chem. Rev., 2007, 107, 2546
8. F. M. Kerton, Alternative Solvents for Green Chemistry, RSC Publishing, Cambridge, 2009
9. S. Narayan, J. Muldoon, M. G. Finn, V. V. Fokin, H. C. Kolb and K. B. Sharpless, Angew. Chem. Int. Ed., 2005, 44, 3275
10. Y. Hayashi, Angew. Chem. Int. Ed., 2006, 45, 8103
11. Aqueous-Phase Organometallic Catalysis: Concepts and Applications, eds B. Cornils and W. A. Hermann, Wiley-VCH Verlag GmbH, Weinheim, 1998
12. F. Joó, Aqueous Organometallic Catalysis, Kluwer, Dordrecht, 2001
13. N. Pinault and D. W. Bruce, Coord. Chem. Rev., 2003, 241, 1
14. K. H. Shaughnessy, Chem. Rev., 2009, 109, 643
15. C. O. Kappe, Angew. Chem. Int. Ed., 2004, 43, 6250
16. C. O. Kappe, Chem. Soc. Rev., 2008, 37, 1127
17. C. R. Strauss, Aust. J. Chem., 2009, 62, 3
18. V. Polshettiwar, M. N. Nadagouda and R. S. Varma, Aust. J. Chem., 2009, 62, 16
19. M. J. Gronnow, R. J. White, J. H. Clark and D. J. Macquarrie, Org. Process Res. Dev., 2005, 9, 516
20. P. Appukkuttan and E. Van der Eycken, Eur. J. Org. Chem., 2008, 1133
21. S. Caddick and R. Fitzmaurice, Tetrahedron, 2009, 65, 3355.
22. F. Nicks, Y. Borguet, S. Delfosse, D. Bicchielli, L. Delaude, X. Sauvage and A. Demonceau, Aust. J. Chem., 2009, 62, 184
23. D. Dallinger and C. O. Kappe, Chem. Rev., 2007, 107, 2563
24. V. Polshettiwar and R. S. Varma, Acc. Chem. Res., 2008, 41, 629
25. V. Polshettiwar and R. S. Varma, Chem. Soc. Rev., 2008, 37, 1546
26. The Amide Linkage: Structural Significance in Chemistry, Biochemistry and Material Science, ed. A. Greenberg, C. M. Breneman and J. F. Liebman, John Wiley & Sons, Inc., New York, 2000
27. I. Johansson, in Kirk-Othmer Encyclopedia of Chemical Technology, John Wiley & Sons, Hoboken NJ, 5th edn., 2004, Vol. 2, p. 442
28. N. A. Bokach and V. Y. Kukushkin, Russ. Chem. Rev., 2005, 74, 153
29. V. Y. Kukushkin and A. J. L. Pombeiro, Inorg. Chim. Acta, 2005, 358, 1
30. V. Cadierno, J. Francos and J. Gimeno, Chem. Eur. J., 2008, 14, 6601
31. V. Polshettiwar and R. S. Varma, Chem. Eur. J., 2009, 15, 1582
32. R. S. Ramó n, N. Marion and S. P. Nolan, Chem. Eur. J., 2009, 15, 8695
33. K. Manjula and M. A. Pasha, Synth. Commun., 2007, 37, 1545
34. A. D. Allen, Y. Chiang, A. J. Kresge and T. T. Tidwell, J. Org. Chem., 1982, 47, 775
35. T. Tsuchimoto, T. Joya, E. Shirakawa and Y. Kawakami, Synlett, 2000, 1777
36. F. Alonso, I. P. Beletskaya and M. Yus, Chem. Rev., 2004, 104, 3079
37. L. Chen and C.-J. Li, Adv. Synth. Catal., 2006, 348, 1459
38. J. M. Kremsner and C. O. Kappe, Eur. J. Org. Chem., 2005, 3672
39. A. Vasudevan and M. K. Verzal, Synlett, 2004, 631
40. L. Coudray and J.-L. Montchamp, Eur. J. Org. Chem., 2008, 3601
41. M. D. Milton, G. Onodera, Y. Nishibayashi and S. Uemura, Org. Lett., 2004, 6, 3993
42. R. A. Stockland Jr., A. J. Lipman, J. A. Bawiec III, P. E. Morrison, I. A. Guzei, P. M. Findeis and J. F. Tamblin, J. Organomet. Chem., 2006, 691, 4042
43. H. Yamamoto, in: Comprehensive Organic Synthesis, ed. B. M. Trost, I. Fleming and C. H. Heathcock, Pergamon Press, Exeter, 1991, Vol. 2, ch. 1.3, p 81
44. L. W. Bieber, M. F. da Silva, R. C. da Costa and L. O. S. Silva, Tetrahedron Lett., 1998, 39, 3655.
45. M.-J. Lin and T.-P. Loh, J. Am. Chem. Soc., 2003, 125, 13042
46. C. Z. Gu, Q. R. Li and H. Yin, Chin. Chem. Lett., 2005, 16, 1573
47. Q.-R. Li, C.-Z. Gu and H. Yin, Chin. J. Chem., 2006, 24, 72
48. L. C. Akullian, M. L. Snapper and A. H. Hoveyda, Angew. Chem. Int. Ed., 2003, 42, 4244
49. L. Zani and C. Bolm, Chem. Commun., 2006, 20, 4263
50. L. Shi, Y.-Q. Tu, M. Wang, F.-M. Zhang and C.-A. Fan, Org. Lett., 2004, 6, 1001
51. C. Wei and C.-J. Li, J. Am. Chem. Soc., 2003, 125, 9584
52. R. C. van der Drift, E. Bouwman and E. Drent, J. Organomet. Chem., 2002, 650, 1
53. R. Uma, C. Cre'visy and R. Gré e, Chem. Rev., 2003, 103, 27
54. V. Cadierno, P. Crochet and J. Gimeno, Synlett, 2008, 1105
55. S. H. Bergens and B. Bosnich, J. Am. Chem. Soc., 1991, 113, 958
56. D. V. McGrath and R. H. Grubbs, Organometallics, 1994, 13, 224
57. P. Crochet, J. Di'ez, M. A. Fernández-Zúmel and J. Gimeno, Adv. Synth. Catal., 2006, 348, 93
58. K. Ishibashi, M. Takahashi, Y. Yokota, K. Oshima and S. Matsubara, Chem. Lett., 2005, 34, 664
59. M. Takahashi, K. Oshima and S. Matsubara, Tetrahedron Lett., 2003, 44, 9201
60. D. Wang, D. Chen, J. X. Haberman and C.-J. Li, Tetrahedron, 1998, 54, 5129 and references cited therein
61. G. Liu, Y. Sun, J. Wang, C. Sun, F. Zhang and H. Li, Green Chem., 2009, 11, 1477
62. S. Swaminathan and K. V. Narayanan, Chem. Rev., 1971, 71, 429
63. D. A. Engel and G. B. Dudley, Org. Biomol. Chem., 2009, 7, 4149
64. V. Cadierno, P. Crochet, S. E. Garci'a-Garrido and J. Gimeno, Dalton Trans., (DOI: 10.1039/b923602c)
65. V. Cadierno, J. Francos and J. Gimeno, Tetrahedron Lett., 2009, 50, 4773
66. Synthesis and Applications of Isotopically Labelled Compounds, ed. D. Dean, C. N. Filer and K. E. McCarthy, John Wiley and Sons, Ltd., London, 2004
67. J. Atzrodt, V. Derdau, T. Fey and J. Zimmermann, Angew. Chem. Int. Ed., 2007, 46, 7744
68. M. Takahashi, K. Oshima and S. Matsubara, Chem. Lett., 2005, 34, 192
69. K. Ishibashi and S. Matsubara, Chem. Lett., 2007, 36, 724
70. E. A. Cioffi, R. H. Bell and B. Le, Tetrahedron: Asymmetry, 2005, 16, 471
71. S. S. Bokatzian-Johnson, M. L. Maier, R. H. Bell, K. E. Alston, B. Y. Le and E. A. Cioffi, J. Labelled Compd. Radiopharm., 2007, 50, 380
72. M. Yamamoto, K. Oshima and S. Matsubara, Org. Lett., 2004, 6, 5015
73. J. M. Barthez, A. V. Filikov, L. B. Frederiksen, M.-L. Huguet, J. R. Jones and S.-Y. Lu, Can. J. Chem., 1998, 76, 726
74. S. Anto, G. S. Getvoldsen, J. R. Harding, J. R. Jones, S.-Y. Lu and J. C. Russell, J. Chem. Soc., Perkin Trans. 2, 2000, 2, 2208
75. W.-M. Yau and K. Gawrisch, J. Labelled Compd. Radiopharm., 1999, 42, 702
76. V. Derdau, J. Atzrodt, J. Zimmermann, C. Kroll and F. Brückner, Chem. Eur. J., 2009, 15, 10397
77. N. Ito, T. Watahiki, T. Maesawa, T. Maegawa and H. Sajiki, Adv. Synth. Catal., 2006, 348, 1025
78. N. Ito, T. Watahiki, T. Maesawa, T. Maegawa and H. Sajiki, Synthesis, 2008, 1467
79. V. Birke, Terratech., 1998, 7, 52
80. F. Kastanek and M. Kuras, Environ. Studies, 2004, 10, 441
81. F. Kastanek, Y. Maletorova, P. Katanek, J. Rott, V. Jiricny and K. Jiratova, Desalination, 2007, 21, 261
82. H. Hidaka, A. Saitou, H. Honjou, K. Hosoda, M. Moriya and N. Serpone, J. Hazard. Mat., 2007, 148, 22
83. K. Kunz, U. Scholz and D. Ganzer, Synlett, 2003, 2428
84. F. Monnier and M. Taillefer, Angew. Chem. Int. Ed., 2008, 47, 3096
85. F. Monnier and M. Taillefer, Angew. Chem. Int. Ed., 2009, 48, 6954
86. X. Zhu, Y. Ma, L. Su, H. Song, G. Chen, D. Liang and Y. Wan, Synthesis, 2006, 3955
87. S. Röttger, P. J. R. Sjöberg and M. Larhed, J. Comb. Chem., 2007, 9, 204
88. L. D. S. Yadav, B. S. Yadav and V. K. Rai, Synthesis, 2006, 1868
89. A. Martín, R. F. Pellón, M. Mesa, M. L. Docampo and V. Gómez, J. Chem. Res., 2005, 561
90. D. Guo, H. Huang, Y. Zhou, J. Xu, H. Jiang, K. Chen and H. Liu, Green Chem., 2010, 12, 276
91. M. C. Bagley, M. C. Dix and V. Fusillo, Tetrahedron Lett., 2009, 50, 3661
92. D. D. Weller, E. P. Stirchak and A. Yokoyama, J. Org. Chem., 1984, 49, 2061
93. C. M. Kormos and N. E. Leadbeater, Tetrahedron, 2006, 62, 4728
94. J. Andersen, U. Madsen, F. Björkling and X. Liang, Synlett, 2005, 2209
95. T. A. Bryson, J. J. Stewart, J. M. Gibson, P. S. Thomas and J. K. Berch, Green Chem., 2003, 5, 174
96. R. R. Poondra and N. J. Turner, Org. Lett., 2005, 7, 863
97. T. Shibata, Adv. Synth. Catal., 2006, 348, 2328
98. D. Strübing and M. Beller, Top. Organomet. Chem., 2006, 18, 165
99. H. W. Lee, F. Y. Kwong and A. S. C. Chan, Synlett, 2008, 1553
100. T. E. Müller and M. Beller, Chem. Rev., 1998, 98, 675
101. F. Pohlki and S. Doye, Chem. Soc. Rev., 2003, 32, 104
102. D. Ye, J. Wang, X. Zhang, Y. Zhou, X. Ding, E. Feng, H. Sun, G. Liu, H. Jiang and H. Liu, Green Chem., 2009, 11, 1201
103. X. Zhang, D. Ye, H. Sun, D. Guo, J. Wang, H. Huang, X. Zhang, H. Jiang and H. Liu, Green Chem., 2009, 11, 1881
104. O. Arjona, A. M. Gó mez, J. C. Ló pez and J. Plumet, Chem. Rev., 2007, 107, 1919
105. K.-S. Ko, C. J. Zea and N. L. Pohl, J. Am. Chem. Soc., 2004, 126, 13188
106. I.-H. Chen, J.-N. Young and S. J. Yu, Tetrahedron, 2004, 60, 11903
107. W. H. Binder and R. Sachsenhofer, Macromol. Rapid Commun., 2007, 28, 15
108. R. Huisgen, Angew. Chem. Int. Ed. Engl., 1963, 2, 565
109. V. V. Rostovtsev, L. G. Green, V. V. Fokin and K. B. Sharpless, Angew. Chem. Int. Ed., 2002, 41, 2596
110. C. W. Tornoe, C. Christensen and M. Medal, J. Org. Chem., 2002, 67, 3057
111. P. Appukkuttan, W. Dehaen, V. V. Fokin and E. van der Eycken, Org. Lett., 2004, 6, 4223
112. N. Kaval, D. Ermolat'ev, P. Appukkuttan, W. Dehaen, C. O. Kappe and E. Van der Eycken, J. Comb. Chem., 2005, 7, 490
113. D. Ermolat'ev, W. Dehaen and E. van der Eycken, QSAR Comb. Sci., 2004, 23, 915
114. D. S. Ermolat'ev, V. P. Mehta and E. van der Eycken, QSAR Comb. Sci., 2007, 26, 1266
115. C. Bouillon, A. Meyer, S. Vidal, A. Jochum, Y. Chevolot, J.-P. Cloarec, J.-P. Praly, J.-J. Vasseur and F. Morvan, J. Org. Chem., 2006, 71, 4700
116. H. S. G. Beckmann and V. Wittmann, Org. Lett., 2007, 9, 1
117. G. R. Newkome, C. N. Moorefield and F. Vögtle, in Dendrimers and Dendrons: Concepts, Syntheses, Applications, John Wiley & Sons, Inc., New York, 2001
118. D. T. S. Rijkers, G. W. van Esse, R. Merkx, A. J. Brouwer, H. J. F. Jacobs, R. J. Pieters and R. M. J. Liskamp, Chem. Commun., 2005, 4581
119. J. A. F. Joosten, N. T. H. Tholen, F. A. E. Maate, A. J. Brouwer, G. W. van Esse, D. T. S. Rijkers, R. M. J. Liskamp and R. J. Pieters, Eur. J. Org. Chem., 2005, 3182
120. I. Dijkgraaf, A. Y. Rijnders, A. Soede, A. C. Dechesne, G. W. van Esse, A. J. Brouwer, F. H.M. Corstens, O. C. Boerman, D. T. S. Rijkers and R. M. J. Liskamp, Org. Biomol. Chem., 2007, 5, 935
121. K. Yoon, P. Goyal and M. Weck, Org. Lett., 2007, 9, 2051
122. S. E. Clapman, A. Hadzovic and R. H. Morris, Coord. Chem. Rev., 2004, 248, 220
123. S. Gladiali and A. Alberico, Chem. Soc. Rev., 2006, 35, 22
124. J. S. M. Samec, J.-E. Bäckvall, P. G. Andersson and P. Brandt, Chem. Soc. Rev., 2006, 35, 23
125. T. Ikariya and A. J. Blacker, Acc. Chem. Res., 2007, 40, 1300
126. A. Sharma, B. P. Joshi and A. K. Sinha, Chem. Lett., 2003, 32, 1186
127. A. Sharma, V. Kumar and A. K. Sinha, Adv. Synth. Catal., 2006, 348, 354
128. V. Kumar, A. Sharma and A. K. Sinha, Helv. Chim. Acta, 2006, 89, 483
129. B. L. A. P. Devi, M. S. L. Karuna, K. N. Rao, P. S. Saiprasad and R. B. N. Prasad, J. Am. Oil Chem. Soc., 2003, 80, 1003
130. A. R. Katrizky, O. Meth-Cohn and C. W. Rees, (eds), Comprehensive Organic Functional Group Transformations, Pergamon, London, 1995 Vol. 3
131. I. T. Harrison and S. Harrison (eds), Compendium of Organic Synthetic Methods, John Wiley & Sons, Inc., New York, 1971, Vol. 1
132. A. Miyazawa, K. Tanaka, T. Sakakura, M. Tashiro, H. Tashiro, G. K. S. Prakash and G. A. Olah, Chem. Commun., 2005, 2104
133. A. Miyazawa, K. Saitou, K. Tanaka, T. M. Gädda, M. Tashiro, G. K. S. Prakash and G. A. Olah, Tetrahedron Lett., 2006, 47, 1437
134. W. Bonrath, R. Karge, M. Nuechter and B. Ondruschka, PCT Int. Appl., WO 03/091235 A1 (CAN 139:360625), 2003
135. M. Bonchio, M. Carraro, A. Sartorel, G. Scorrano and U. Kortz, J. Mol. Catal. A: Chem., 2006, 251, 93
136. X. Liu, X. Quan, L. Bo, S. Chen, Y. Zhao and M. Chang, Appl. Catal. A, 2004, 264, 53
137. L. L. Bo, Y. B. Zhang, X. Quan and B. Zhao, J. Hazard. Mater., 2008, 153, 1201
138. L. Bo, X. Quan, X. Wang and S. Chen, J. Hazard. Mater., 2008, 157, 179
139. X. Bi, P. Wang and H. Jiang, J. Hazard. Mater., 2008, 154, 543
140. D. Castagnolo, L. Botta and M. Botta, J. Org. Chem., 2009, 74, 3172
141. R. Hosseinzadeh, A. Sharifi, K. Tabar-Heydar and F. Mohsenzadeh, Monatsh. Chem., 2002, 133, 1413.
142. A. Procopio, M. Gaspari, M. Nardi, M. Oliverio and R. Romeo, Tetrahedron Lett., 2008, 49, 1961.