Green solvents for sustainable organic synthesis: State of the art

Green Chemistry

Volumn 7, Issue 5, 2005, Pages 267-278

  Sheldon, Roger A ^a,b  

^a UNIVERSITY OF LEICESTER   (United Kingdom)

^b DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

CARBON DIOXIDE; FLUORINE DERIVATIVE; GREEN SOLVENT; SOLVENT; UNCLASSIFIED DRUG; WATER;

CATALYST; CHEMICAL REACTION; CONFERENCE PAPER; ORGANIC CHEMISTRY; SUPERCRITICAL FLUID; SYNTHESIS;

EID: 19744366251     PISSN: 14639262     EISSN: 14639270     Source Type: Journal    
DOI: 10.1039/b418069k     Document Type: Conference Paper

References (101)

1. R. A. Sheldon, C. R. Acad. Sci., Ser. IIc: Chim., 2000, 3, 541-551;
2. R. A. Sheldon, Chem. Ind. (London), 1997, 12-15;
3. R. A. Sheldon, Pure Appl. Chem., 2000, 72, 1233-1246;
4. R. A. Sheldon, Russ. Chem. J., 2000, 44, 9-20.
5. White Biotechnology: Gateway to a more Sustainable Future, Europabio Report, 2003, http://www.europabio.org.
6. D. J. C. Constable, A. D. Curzons and V. L. Cunningham, Green Chem., 2002, 4, 521-527.
7. A. M. Rouhi, Chem. Eng. News, April 2002, 31-32;
8. G. P. Taber, D. M. Pfistere and J. C. Colberg, Org. Proc. Res. Dev., 2004, 8, 385-388.
9. A. Haimov and R. Neumann, Chem. Commun., 2002, 876-877;
10. see also H. Alper, K. Januszkiewicz and D. J. H. Smith, Tetrahedron Lett., 1985, 26, 2263-2264.
11. S. Chanrasekhar, Ch. Narsihmulu, S. S. Sultana and N. R. Reddy, Org. Lett., 2002, 4, 4399-4401.
12. G. Papadogianakis and R. A. Sheldon, in Catalysis, Vol. 13, Specialist Periodical Report, Royal Society of Chemistry, Cambridge, UK, 1997, pp. 114-193;
13. Aqueous Phase Organometallic Catalysis. Concepts and Applications, ed. B. Cornils and W. A. Herrmann, Wiley-VCH, Weinheim, 1998.
14. B. Cornils and E. Wiebus, Recl. Trav. Chim. Pays-Bas, 1996, 115, 211-215.
15. F. Joo and M. T. Beck, React. Kinet. Catal. Lett., 1975, 2, 257-263;
16. F. Joo and Z. Toth, J. Mol. Catal., 1980, 8, 369-383.
17. E. G. Kuntz, CHEMTECH, 1987, 17, 570-575;
18. E. G. Kuntz, French Pat., 2 314 910, 1975.
19. G. Papadogianakis, L. Maat and R. A. Sheldon, J. Chem. Soc., Chem. Commun., 1994, 1887-1888.
20. G. Papadogianakis, J. A. Peters, L. Maat and R. A. Sheldon, J. Chem. Soc., Chem. Commun., 1995, 1105-1106.
21. G. Papadogianakis, L. Maat and R. A. Sheldon, J. Mol. Catal. A: Chem., 1997, 116, 179-190.
22. G. Papadogianakis, L. Maat and R. A. Sheldon, J. Chem. Technol. Biotechnol., 1997, 70, 83-91.
23. G. Verspui, I. I. Moiseev and R. A. Sheldon, J. Organomet. Chem., 1999, 586, 196-199.
24. W. Kohlpaintner and M. Beller, J. Mol. Catal. A: Chem., 1997, 116, 259-267.
25. G. Papadogianakis, G. Verspui, L. Maat and R. A. Sheldon, Catal. Lett., 1997, 47, 43-46.
26. S. Tilloy, E. Monflier, E. Bertoux, Y. Castanet and A. Mortreux, New J. Chem., 1997, 21, 529-531.
27. G. Verspui, G. Papadogianakis and R. A. Sheldon, Chem. Commun., 1998, 401-402;
28. G. Verspui, F. Schanssema and R. A. Sheldon, Appl. Catal., A: Gen., 2000, 198, 5-11.
29. G. Verspui, F. Schanssema and R. A. Sheldon, Angew. Chem., Int. Ed., 2000, 39, 804-806.
30. G. J. ten Brink, I. W. C. E. Arends and R. A. Sheldon, Science, 2000, 287, 1636-1639.
31. R. Noyori, M. Aoki and K. Sato, Chem. Commun., 2003, 1977-1986 and references cited therein.
32. A. J. J. Straathof, S. Panke and A. Schmid, Curr. Opin. Biotechnol., 2002, 13, 548-556.
33. K. A. Powell, S. W. Ramer, S. B. del Cardayré, W. P. C. Stemmer, M. B. Tobin, P. F. Longchamp and G. W. Huisman, Angew. Chem., Int. Ed., 2001, 40, 3948-3959.
34. M. A. Wegman, M. H. A. Janssen, F. van Rantwijk and R. A. Sheldon, Adv. Synth. Catal., 2001, 343, 559-576.
35. K. Oyama, The industrial production of aspartame, in Chirality in Industry, ed. A. N. Collins, G. N. Sheldrake and J. Crosby, Wiley, New York, 1992, pp. 237-248.
36. J. E. Gavagan, S. K. Fager, J. E. Seip, M. S. Payne, D. L. Anton and R. DiCosimo, J. Org. Chem., 1995, 60, 3957-3963.
37. W. Stampfer, B. Kosjek, C. Moitzi, W. Kroutil and K. Faber, Angew. Chem., Int. Ed., 2002, 41, 1014-1017.
38. Special Issue on Green Solvents for Catalysis, ed. W. Leitner, K. R. Seddon, P. Wasserscheid, Green Chem., 2003, 5, 99-284;
39. see also P. G. Jessop, R. R. Stanley, R. A. Brown, C. A. Eckert, C. L. Liotta, T. T. Ngo and P. Pollet, Green Chem., 2003, 5, 123-128;
40. J. Liu, M. J. Lazzaroni, J. P. Hallett, A. S. Bommarius, C. L. Liotta and C. A. Eckert, Ind. Eng. Chem. Res., 2004, 43, 1586-1590;
41. C. A. Eckert, C. L. Liotta, D. Bush, J. S. Brown and J. P. Hallett, J. Phys. Chem. B, 2004, 108, 18108-18118.
42. W. Leitner, Top. Curr. Chem., 1999, 206, 107-132;
43. W. Leitner, Acc. Chem. Res., 2002, 35, 746-756;
44. E. J. Beckman, J. Supercrit. Fluids, 2004, 28, 121-191.
45. P. Licence, J. Ke, M. Sokolova, S. K. Ross and M. Poliakoff, Green Chem., 2003, 5, 99-104
46. 2 see: M. J. Burk, S. Feng, M. F. Gross and W. J. Tumas, J. Am. Chem. Soc., 1995, 117, 8277-8278.
47. N. J. Meehan, A. J. Sandee, J. N. H. Reek, P. C. J. Kamer, P. W. N. M. van Leeuwen and M. Poliakoff, Chem. Commun., 2000, 1497-1498.
48. E. J. Beckmann, Green Chem., 2003, 5, 332-336.
49. T. Danciu, E. J. Beckman, D. Hancu, R. Cochran, R. Grey, D. Hajnik and J. Jewson, Angew. Chem., Int. Ed., 2003, 42, 1140-1142.
50. (a) T. W. Randolph, H. W. Blanch, J. M. Prausnitz and C. R. Wilke, Biotechnol. Lett., 1985, 7, 325-328;
51. (b) D. A. Hammond, M. Karel, A. M. Klibanov and V. J. Krukonis, Appl. Biochem. Biotechnol., 1985, 11, 393-400;
52. (c) K. Nakamura, Y. M. Chi, Y. Yamada and T. Yano, Chem. Eng. Commun., 1986, 45, 207.
53. T. Matsuda, T. Harada and K. Nakamura, Green Chem., 2004, 6, 440-444.
54. A. Overmeyer, S. Schrader-Lippelt, V. Kascher and G. Brunner, Biotechnol. Lett., 1999, 21, 65-69.
55. T. Matsuda, R. Kanamaru, K. Watanabe, T. Harada and K. Nakamura, Tetrahedron Lett., 2001, 42, 8319-8321;
56. T. Matsuda, R. Kanamaru, K. Watanabe, T. Kamitanaka, T. Harada and K. Nakamura, Tetrahedron: Asymmetry, 2003, 14, 2087-2091.
57. T. Matsuda, K. Watanabe, T. Harada, K. Nakamura, Y. Arita, Y. Misumi, S. Ichikawa and T. Ikariya, Chem. Commun., 2004, 2286-2287.
58. T. Matsuda, K. Watanabe, T. Kamitanaka, T. Harada and K. Nakamura, Chem. Commun., 2003, 1198-1199.
59. T. W. Randolph, D. S. Clark, H. W. Blanch and J. M. Prausnitz, Science, 1988, 239, 387-390.
60. I. T. Horváth and J. Rabai, Science, 1994, 266, 72-75;
61. I. T. Horváth, Acc. Chem. Res., 1998, 31, 641-650.
62. Handbook of Fluorous Chemistry, ed. J. A. Gladysz, D. P. Curran and I. T. Horváth, Wiley, Weinheim, 2004.
63. I. T. Horváth, G. Kiss, R. A. Cook, J. E. Bond, P. A. Stevens, J. Rábai and E. J. Mozeleski, J. Am. Chem. Soc., 1998, 120, 3133-3143.
64. See also D. F. Foster, D. Gudmunsen, D. J. Adams, A. M. Stuart, E. G. Hope, D. J. Cole-Hamilton, G. P. Schwarz and P. Pogorzelec, Tetrahedron, 2002, 58, 3901-3910.
65. B. Betzemeier, M. Cavazinne, S. Quici and P. Knochel, Tetrahedron Lett., 2000, 41, 4343-4346.
66. G.-J. ten Brink, J. M. Vis, I. W. C. E. Arends and R. A. Sheldon, Tetrahedron, 2002, 58, 3977-3983;
67. G.-J. ten Brink, J. M. Vis, I. W. C. E. Arends and R. A. Sheldon, J. Org. Chem., 2001, 66, 2429-2433;
68. G.-J. ten Brink, B. C. M. Fernandes, M. C. A. van Vliet, I. W. C. E. Arends and R. A. Sheldon, J. Chem. Soc., Perkin Trans. 1, 2001, 224-228.
69. M. Wende, R. Meier and J. A. Gladysz, J. Am. Chem. Soc., 2001, 123, 11490-11491;
70. M. Wende and J. A. Gladysz, J. Am. Chem. Soc., 2003, 125, 5861-5872.
71. M. C. A. van Vliet, I. W. C. E. Arends and R. A. Sheldon, Chem. Commun., 1999, 263-264.
72. Ionic Liquids as Green Solvents; Progress and Prospects, ed. R. D. Rogers and K. R. Seddon, ACS Symp. Ser. 856, American Chemical Society, Washington DC, 2003;
73. Ionic Liquids in Synthesis, ed. P. Wasserscheid and T. Welton, Wiley-VCH, Weinheim, 2003.
74. For recent reviews see: R. A. Sheldon, Chem. Commun., 2001, 2399-2407;
75. P. Wasserscheid and W. Keim, Angew. Chem., Int. Ed., 2000, 39, 3772-3789;
76. J. Dupont, R. F. de Souza and P. A. Z. Suarez, Chem. Rev., 2002, 102, 3667-3692;
77. C. E. Song, Chem. Commun., 2004, 1033-1043.
78. P. Wasserscheid, H. Waffenschmidt, P. Machnitzki, K. W. Kottsieper and O. Stelzer, Chem. Commun., 2001, 451-452;
79. P. W. N. M. van Leeuwen, P. C. J. Kamer, J. N. H. Reek and P. Dierkes, Chem. Rev., 2000, 100, 2741-2770;
80. R. P. J. Bronger, S. M. Silva, P. C. J. Kramer and P. W. N. M. van Leeuwen, Chem. Commun., 2002, 3044-3045.
81. For reviews see: F. van Rantwijk, R. Madeira Lau and R. A. Sheldon, Trends Biotechnol., 2003, 21, 131-138;
82. R. A. Sheldon, R. Madeira Lau, M. J. Sorgedrager, F. van Rantwijk and K. R. Seddon, Green Chem., 2002, 4, 147-151;
83. U. Kragl, M. Eckstein and N. Kaftzik, Curr. Opin. Biotechnol., 2002, 13, 565-571.
84. R. Madeira Lau, F. van Rantwijk, K. R. Seddon and R. A. Sheldon, Org. Lett., 2000, 2, 4189-4191.
85. Q. Liu, M. H. A. Janssen, F. van Rantwijk and R. A. Sheldon, Green Chem., 2005, 7, 39-42.
86. See, for example, N. Gathergood and P. J. Scammels, Aust. J. Chem., 2002, 55, 557-560.
87. R. A. Brown, P. Pollet, E. McKoon, C. A. Eckhert, C. L. Liotta and P. G. Jessop, J. Am. Chem. Soc., 2001, 123, 1254-1255;
88. D. J. Cole-Hamilton, Science, 2003, 299, 1702-1706;
89. F. Liu, M. B. Abrams, R. T. Baker and W. Tumas, Chem. Commun., 2001, 433-434.
90. P. Lozano, T. de Diego, D. Carrié, M. Vaultier and J. L. Iborra, Chem. Commun., 2002, 692-693;
91. M. T. Reetz, W. Wiesenhofer, G. Francio and W. Leitner, Chem. Commun., 2002, 992-993;
92. P. Lozano and T. de Diego, Biotechnol. Prog., 2004, 20, 661-669.
93. M. C. Kroon, A. Shariati, M. Costantini, J. van Spronsen, G.-J. Witkamp, R. A. Sheldon and C. J. Peters, J. Chem. Eng. Data, 2005, 50, 173-176.
94. D. J. Heldebrandt and P. G. Jessop, J. Am. Chem. Soc., 2003, 125, 5600-5601.
95. D. E. Bergbreiter, Chem. Rev., 2002, 102, 3345-3383.
96. A. E. Ivanov, E. Edink, A. Kumar, I. Y. Galaev, A. F. Arendsden, A. Bruggink and B. Mattiasson, Biotechnol. Prog., 2003, 19, 1167-1175.
97. A. Bruggink, R. Schoevaart and T. Kieboom, Org. Proc. Res. Dev., 2003, 7, 622-640.
98. R. Schoevaart and T. Kieboom, Tetrahedron Lett., 2002, 43, 3399-3400.
99. C. Simons, U. Hanefeld, I. W. C. E. Arends, A. J. Minnaard, T. Maschmeyer and R. A. Sheldon, Chem. Commun., 2004, 2830-2831.
100. L. Cao, L. M. van Langen and R. A. Sheldon, Curr. Opin. Biotechnol., 2003, 14, 387-394.
101. C. Mateo, manuscript in preparation.