Organocatalytic reactions: Effects of ball milling, microwave and ultrasound irradiation

Green Chemistry

Volumn 10, Issue 11, 2008, Pages 1131-1141

  Bruckmann, Angelika ^a   Krebs, Anke ^a   Bolm, Carsten ^a  

^a RWTH AACHEN UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 54949089047     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/b812536h     Document Type: Article

References (94)

1. For overviews on green and sustainable chemistry, see: Green Chemistry: Theory and Practice, ed. P. T. Anastas and J. C. Warner, Oxford University Press, Oxford, 1998.
2. Handbook of Green Chemistry and Technology, ed. J. Clark and D. Macquarrie, Blackwell Science, Oxford, 2002.
3. J. H. Clark Green Chem. 2006 8 17-21.
4. Reviews: G. Kaupp, M. R. Naimi-Jamal, H. Ren and H. Zoz, in Advanced Technologies Based on Self-Propagating and Mechano-chemical Reactions for Environmental Protection, ed. G. F. Cao, Delogu and R. Orrù, Research Signpost, Kerala, 2003, pp. 83–100.
5. E. Gaffet F. Bernard J.-C. Niepce F. Charlot C. Gras G. Le Caër J.-L. Guichard P. Delcroix A. Mocellin O. Tillement J. Mater. Chem. 1999 9 305-314.
6. S. V. Kipp, Sepelak K. D. Becker Chem. Unserer Zeit 2005 39 384-392.
7. For an overview on solvent-free organic reactions, see: G. W. V. Cave C. L. Raston J. L. Scott Chem. Commun. 2001 2159-2169.
8. K. Tanaka, Solvent-Free Organic Synthesis, Wiley-VCH, Weinheim, 2003.
9. P. J. Walsh H. Li C. A. de Parrodi Chem. Rev. 2007 107 2503-2545.
10. B. Rodríguez A. Bruckmann T. Rantanen C. Bolm Adv. Synth. Catal. 2007 349 2213-2233.
11. G. Kaupp CrystEngComm 2006 8 794-804.
12. K. Komatsu Top. Curr. Chem. 2005 254 185-206.
13. A. L. Garay A. Pichon S. L. James Chem. Soc. Rev. 2007 36 846-855.
14. J. M. Harrowfield R. J. Hart C. R. Whitaker Aust. J. Chem. 2001 54 423-425.
15. For organic solid-state synthesis, see: G. Kaupp J. Schmeyers J. Boy Chemosphere 2001 43 55-61.
16. G. Rothenberg A. P. Downie C. L. Raston C. L. Raston J. L. Scott J. Am. Chem. Soc. 2001 123 8701-8708.
17. G. Kaupp CrystEngComm 2003 5 117-133.
18. F. Toda Acc. Chem. Res. 1995 28 480-486.
19. For an overview on organic solid-state reactions mostly with application of a ball mill, see: G. Kaupp Top. Curr. Chem. 2005 254 95-183.
20. In 1984, Heinicke defined the concept of mechanochemistry as follows: “Mechanochemistry is the branch of chemistry, which studies the solid-state physical and chemical transformations, which are induced by the application of mechanical influence”. G. Heinicke, Tribochemistry, Akademie Verlag, Berlin, 1984.
21. For selected reviews on mechanochemistry, see: J. F. Fernandez-Bertran Pure Appl. Chem. 1999 71 581-586.
22. V. V. Boldyrev K. Tkácová J. Mater. Synth. Process. 2000 8 121-132.
23. M. K. Beyer H. Clausen-Schaumann Chem. Rev. 2005 105 2921-2948.
24. F. K. Urakaev V. V. Boldyrev Powder Technol. 2000 107 93-107.
25. F. K. Urakaev V. V. Boldyrev Powder Technology 2000 107 197-206.
26. for a qualitative summary of this model, see ref. 2c.
27. For some selected examples, see: B. List R. A. Lerner C. F. Barbas III J. Am. Chem. Soc. 2000 122 2395-2396.
28. P. M. Pihko K. M. Laurikainen A. Usano A. I. Nyberg J. A. Kaavi Tetrahedron 2006 62 317-328.
29. Review:G. Guillena C. Nájera D. J. Ramón Tetrahedron: Asymmetry 2007 18 2249-2293.
30. B. Rodríguez T. Rantanen C. Bolm Angew. Chem., Int. Ed. 2006 45 6924-6926.
31. B. Rodríguez T. Rantanen C. Bolm Angew. Chem. 2006 118 7078-7080.
32. B. Rodríguez A. Bruckmann C. Bolm Chem.–Eur. J. 2007 13 4710-4722.
33. T. Rantanen I. Schiffers C. Bolm Org. Process Res. Dev. 2007 11 592-597.
34. Y. Sekiguchi A. Sasaoka A. Shimomoto S. Fujioka H. Kotsuki Synlett 2003 1655-1658.
35. Z. Tang Z.-H. Yang X.-H. Chen L.-F. Cun A.-Q. Mi Y.-Z. Jiang L.-Z. Gong J. Am. Chem. Soc. 2005 127 9285-9289.
36. Y. Hayashi T. Sumiya J. Takahashi H. Gotoh T. Urushima M. Shoji Angew. Chem., Int. Ed. 2006 45 958-961.
37. Y. Hayashi T. Sumiya J. Takahashi H. Gotoh T. Urushima M. Shoji Angew. Chem. 2006 118 972-975.
38. M. Jiang S.-F. Zhu Y. Yang L.-Z. Gong X.-G. Zhou Q.-L. Zhou Tetrahedron: Asymmetry 2006 17 384-387.
39. Y. Hayashi S. Aratake T. Itoh T. Okana T. Sumiya M. Shoji Chem. Commun. 2007 957-959.
40. G. Guillena M. del Carmen Hita C. Nájera S. F. Viózquez Tetrahedron: Asymmetry 2007 18 2300-2304.
41. G. Guillena M. del Carmen Hita C. Nájera S. F. Viózquez J. Org. Chem. 2008 73 5933-5943.
42. For recent overviews on the Baylis–Hillman reaction, see: D. Basavaiah A. J. Rao T. Satyanarayana Chem. Rev. 2003 103 811-891.
43. D. Basavaiah K. V. Rao R. J. Reddy Chem. Soc. Rev. 2007 36 1581-1588.
44. G. Masson C. Housseman J. Zhu Angew. Chem., Int. Ed. 2007 46 4614-4628.
45. G. Masson C. Housseman J. Zhu Angew. Chem. 2007 119 4698-4712.
46. J. Mack M. Shumba Green Chem. 2007 9 328-330.
47. R. Galeazzi G. Martelli G. Mobbili M. Orena S. Rinaldi Org. Lett. 2004 6 2571-2574.
48. S. A. Sikchi P. G. Hultin J. Org. Chem. 2006 71 5888-5891.
49. R. Gedye F. Smith K. Westaway H. Ali L. Baldisera L. Laberge J. R. Rousell Tetrahedron Lett. 1986 27 279-282.
50. For recent reviews and more detailed descriptions see: C. O. Kappe Angew. Chem., Int. Ed. 2004 43 6250-6284.
51. Angew. Chem. 2004 116 6408-6443.
52. M. A. Herrero J. M. Kremsner C. O. Kappe J. Org. Chem. 2008 73 36-47.
53. M. A. Herrero, J. M. Kremsner and C. O. Kappe, Microwaves in Organic Synthesis, ed. A. Loupy, Wiley-VCH, Weinheim, 2nd edn, 2006.
54. L. Perreux A. Loupy Tetrahedron 2001 57 9199-9223.
55. T. Razzaq J. M. Kresmer C. O. Kappe J. Org. Chem. 2008 73 6321-6329.
56. C. O. Kappe and A. Stadler, Microwaves in Organic and Medicinal Chemistry, Wiley-VCH, Weinheim, 2005.
57. P. Lidström J. Tierny B. Wathey J. Westman Tetrahedron 2001 57 9225-9283 and references therein.
58. B. List J. Am. Chem. Soc. 2000 122 9336-9337.
59. B. List P. Pojarliev W. T. Biller H. J. Martin J. Am. Chem. Soc. 2002 124 827-833.
60. W. Notz K. Sakthivel T. Bui G. Zhong C. F. Barbas III Tetrahedron Lett. 2001 42 199-201.
61. A. Córdova W. Notz G. Zhong J. M. Betancort C. F. Barbas III J. Am. Chem. Soc. 2002 124 1842-1843.
62. W. Notz S.-I. Watanabe N. S. Chowdari G. Zhong J. M. Betancort F. Tanaka C. F. Barbas III Adv. Synth. Catal. 2004 346 1131-1140.
63. B. Westermann C. Neuhaus Angew. Chem., Int. Ed. 2005 44 4077-4079.
64. Angew. Chem. 2005 117 4145-4147.
65. B. Rodríguez C. Bolm J. Org. Chem. 2006 71 2888-2891.
66. For reactions of this type performed without microwave irradiation, see: I. Ibrahem J. Casas A. Córdova Angew. Chem., Int. Ed. 2004 43 6528-6531.
67. I. Ibrahem J. Casas A. Córdova Angew. Chem. 2004 116 6690-6693.
68. I. Ibrahem W. Zou J. Casas H. Sudén A. Córdova Tetrahedron 2006 62 357-364.
69. S. Mossé A. Alexakis Org. Lett. 2006 16 3577-3580.
70. H. Hagiwara S. Inotsume M. Fukushima T. Hoshi T. Suzuki Chem. Lett. 2006 35 926-927.
71. O. Andrey A. Alexakis A. Tomassini G. Bernardinelli Adv. Synth. Catal. 2004 346 1147-1168.
72. M. Hosseini N. Stiasni V. Barbieri C. O. Kappe J. Org. Chem. 2007 72 1417-1424.
73. A. Massi A. Nuzzi A. Dondoni J. Org. Chem. 2007 72 10279-10282.
74. A. Massi A. Dondoni Angew. Chem., Int. Ed. 2008 47 4638-4660.
75. Angew. Chem. 2008 120 4716-4739.
76. M. K. Kundu S. B. Mukherjee N. Balu R. Padmakumar S. V. Bhat Synlett 1994 444.
77. R. Octavio M. A. de Souza M. L. A. A. Vasconcellos Synth. Commun. 2003 33 1383-1389.
78. For the pioneering findings, see: K. A. Ahrendt C. J. Borths D. W. C. MacMillan J. Am. Chem. Soc. 2000 122 4243-4244.
79. W. S. Jen J. J. M. Wiener D. W. C. MacMillan J. Am. Chem. Soc. 2000 122 9874-9875.
80. A. B. Northrup D. W. C. MacMillan J. Am. Chem. Soc. 2002 124 2458-2460.
81. For reviews see: G. Cravotto P. Cintas Chem. Soc. Rev. 2006 35 180-196.
82. G. Cravotto P. Cintas Chem.–Eur. J. 2007 13 1902-1909.
83. C. Einhorn J. Einhorn J.-L. Luche Synthesis 1989 787-813.
84. J. L. Luche C. Einhorn J. Einhorn J. V. Sinisterra-Gago Tetrahedron Lett. 1990 31 4125-4128.
85. C. Einhorn J. Einhorn M. J. Dickens J. L. Luche Tetrahedron Lett. 1990 31 4129-4230.
86. E. B. Flint K. S. Suslick Science 1991 253 1397-1399.
87. For a discussion of some examples, in which “true sonochemical activation” occurs, see ref. 35a.
88. J. Einhorn C. Einhorn J.-L. Luche Synlett 1991 37-38.
89. W. P. Almeida F. Coelho Tetrahedron Lett. 2003 44 937-940.
90. F. G. Coelho C. A. Diaz M. Abella W. P. Almeida Synlett 2006 435-439.
91. M. L. Kantam C. V. Rajasekhar G. Gopikrishna K. R. Reddy B. M. Choudary Tetrahedron Lett. 2006 47 5965-5967.
92. Recently, a very detailed study of solvent-free Knoevenagel condensations was reported. The authors also compared the effect of ball milling and microwave irradiation. With respect to the required energy input the former technique was by far superior to the latter. For details, see: R. Trotzki M. M. Hoffmann B. Ondruschka Green Chem. 2008 10 767-772.
93. A critical analysis of those issues would also have to include aspects such as solvent amount (and energy input) for product extraction, vessel cleaning, product purification by crystallization and/or chromatography etc. To the best of our knowledge, a comprehensive analysis of this type has yet not been reported for organocatalytic reactions.
94. For the application of all three techniques in Heck reactions, see: F. Alonso I. P. Beletskaya M. Yus Tetrahedron 2005 61 11771-11835.