Green Catalytic Oxidations in Water

Metal-Catalyzed Reactions in Water

Volumn , Issue , 2013, Pages 139-172

  Sheldon, Roger A ^a  

^a DELFT UNIVERSITY OF TECHNOLOGY   (Netherlands)

Author keywords

Alcohol oxidation; Biomimetic catalysts; Enzymatic oxidations; Epoxidation; Iron based systems; Metal nanoparticles; Organocatalysts; Palladium complexes; Platinum complexes; Sulfoxidation; TEMPO; Tungsten based systems; Water soluble metal complexes

Indexed keywords

EID: 84885532151     PISSN: None     EISSN: None     Source Type: Book    
DOI: 10.1002/9783527656790.ch5     Document Type: Chapter

References (186)

1. Sheldon, R.A., Arends, I.W.C.E., and Hanefeld, U. (2007) Green Chemistry and Catalysis, Wiley-VCH Verlag GmbH, Weinheim.
2. Kobayashi, S. (ed.) (2012) Water in Organic Synthesis, G. Thieme, Stuttgart.
3. See in Larsson, R. (ed.) (1981) Perspectives in Catalysis: In Commemoration of J. J. Berzelius, CNK Gleerup, Lund, Sweden.
4. Besson, M. and Gallezot, P. (2001) Fine Chemicals through Heterogeneous Catalysis (eds R.A. Sheldon and H. van Bekkum), Wiley-VCH Verlag GmbH, Weinheim, pp. 491-506, 507-518.
5. Hollmann, F., Arends, I.W.C.E., Buehler, K., Schallmey, A., and Bühler, B. (2011) Green Chem., 13, 226.
6. For reviews see: (a) Hutchings, G.J. (2007) Catal. Today, 122, 196
7. Hashmi, S.K. and Hutchings, G.J. (2006) Angew. Chem. Int. Ed., 45, 7896.
8. Christensen, C.H., Rass-Hansen, J., Marsden, C.C., Taarning, E., and Egeblad, K. (2008) ChemSusChem, 1, 283
9. Clark, J.H. (2007) J. Chem. Technol. Biotechnol., 82, 603
10. Lange, J.P. (2007) Biofuels Bioprod. Bioref., 1, 39
11. Dale, B.E. (2007) Biofuels Bioprod. Bioref., 1, 24.
12. Watson, P.A., Wright, L.J., and Fullerton, T.J. (1993) J. Wood Chem. Technol., 13, 371, 391, 411.
13. Hampton, K.W. and Ford, W.T. (1996) J. Mol. Catal. A: Chem., 113, 167.
14. Weinstock, I.A., Atilla, R.H., Reiner, R.S., Moen, M.A., Hammel, K.E., Houtman, C.J., Hill, C.L., and Harrup, M.K. (1997) J. Mol. Catal. A: Chem., 116, 59.
15. Sorokin, A., Séris, J.L., and Meunier, B. (1995) Science, 268, 1163
16. Sorokin, A., DeSuzzoni-Dezard, S., Poullain, D., Noel, J.P., and Meunier, B. (1996) J. Am. Chem. Soc., 118, 7410-7411
17. Meunier, B. and Sorokin, A. (1997) Acc. Chem. Res., 30, 470-476.
18. Kachkarova-Sorokina, S.L., Gallezot, P., and Sorokin, A.B. (2004) Chem. Commun., 2844-2845.
19. Sorokin, A.B., Kachkarova-Sorokina, S.L., Donze, C., Pinel, C., and Gallezot, P. (2004) Top. Catal., 27, 67-76.
20. Collins, T.J. (2002) Acc. Chem. Res., 35, 782-790
21. Banerjee, D., Markley, A.L., Yano, T., Ghosh, A., Berget, P.B., Minkley, E.G., Khetan, S.K., and Collins, T.J. (2006) Angew. Chem. Int. Ed., 45, 3974-3977
22. Chahbane, N., Popescue, D.L., Mitchell, D.A., Chanda, A., Lenoir, D., Ryabov, A.D., Schramm, K.W., and Collins, T.J. (2007) Green Chem., 9, 49-57.
23. Collins, T.J. (1994) Acc. Chem. Res., 27, 279.
24. For reviews of metal-catalyzed epoxidations see: Lane, B.S. and Burgess, K. (2003) Chem. Rev., 103, 2437-2473
25. Bregeault, J.M. (2003) Dalton Trans., 3289-3302.
26. Venturello, G., Alneri, E., and Ricci, M. (1983) J. Org. Chem., 48, 3831-3833.
27. Ishii, Y., Yamawaki, K., Ura, T., Yamada, H., Yoshiba, T., and Ogawa, M. (1988) J. Org.Chem., 53, 3587.
28. Aubry, C., Chottard, G., Platzer, N., Bregeault, J.M., Thouvenot, R., Chauveau, F., Huet, C., and Ledon, H. (1991) Inorg. Chem., 30, 4409.
29. For recent reviews see: Mahha, Y., Salles, L., Piquemal, J.Y., Briot, E., Atlamsami, A., and Bregeault, J.M. (2007) J. Catal., 249, 338-348
30. Bregeault, J.M., Vennat, M., Salles, L., Piquemal, J.Y., Mahha, Y., Briot, E., Bakala, P.C., Atlamsami, A., and Thouvenot, R. (2006) J. Mol. Catal. A: Chem., 250, 177-189.
31. Sato, K., Aoki, M., Ogawa, M., Hashimoto, T., and Noyori, R. (1996) J. Org. Chem., 61, 8310-8311.
32. Noyori, R., Aoki, M., and Sato, K. (2003) Chem. Commun., 1977-1986.
33. Sato, K., Aoki, M., and Noyori, R. (1998) Science, 281, 1646-1647.
34. Maheswari, P.U., de Hoog, P., Hage, R., Gamez, P., and Reedijk, J. (2005) Adv. Synth. Catal., 347, 1759-1764.
35. Xi, Z., Zhou, N., Sun, Y., and Li, K. (2001) Science, 292, 1139-1141.
36. Hage, R. (1996) Recl. Trav. Chim. Pays-Bas, 115, 385
37. see also Hage, R. and Lienke, A. (2006) Angew. Chem. Int. Ed., 45, 206-222.
38. De Vos, D.E., Sels, B.F., Reynaers, M., Subba Rao, Y.V., and Jacobs, P.A. (1998) Tetrahedron Lett., 39, 3221.
39. Berkessel, A. and Sklorz, C.A. (1999) Tetrahedron Lett., 40, 7965.
40. De Vos, D.E., De Wildeman, S., Sels, B.F., Grobet, P.J., and Jacobs, P.A. (1999) Angew. Chem. Int. Ed., 38, 980.
41. Brinksma, J., Schmieder, L., van Vliet, G., Boaron, R., Hage, R., De Vos, D.E., Alsters, P.L., and Feringa, B.L. (2002) Tetrahedron Lett., 43, 2619.
42. Woitiski, C.B., Kozlov, Y.N., Mandeli, D., Nizova, G.V., Schuchardt, U., and Shul'pin, G.B. (2004) J. Mol. Catal. A: Chem., 222, 103-109.
43. Hage, R. and Lienke, A. (2006) J. Mol. Catal. A: Chem., 251, 150-158
44. De Boer, J.W., Brinksma, J., Browne, W.R., Meetsma, A., Alsters, P.L., Hage, R., and Feringa, B. (2005) J. Am. Chem. Soc., 127, 7990.
45. de Boer, J.W., Browne, W.R., Brinksma, J., Alsters, P.L., Hage, R., and Feringa, B.L. (2007) Inorg. Chem., 46, 6353-6372.
46. de Boer, J.W., Browne, W.R., Harutyunyan, S.R., Bini, L., Tiemersma Wegman, T.D., Alsters, P.L., Hage, R., and Feringa, B. (2008) Chem. Commun., 3747-3749.
47. Lane, B.S. and Burgess, K. (2001) J. Am. Chem. Soc., 123, 2933.
48. Lane, B.S., Vogt, M., De Rose, V.J., and Burgess, K. (2002) J. Am. Chem. Soc., 124, 11947.
49. Tong, K.H., Wong, K.Y., and Chan, T.H. (2005) Tetrahedron, 61, 6009-6014.
50. Okrasa, K. and Kazlauskas, R.J. (2006) Chem. Eur. J., 12, 1587.
51. For leading references see: Kazlauskas, R. (2005) Curr. Opin. Chem. Biol., 9, 195
52. Taglieber, A., Höbenreich, H., Carballeira, J.D., Mondiere, R.J.G., and Reetz, M.T. (2007) Angew. Chem. Int. Ed., 46, 8597
53. Reetz, M.T., Mondiere, R., and Carballeira, J.D. (2007) Tetrahedron Lett., 48, 1679
54. Hult, K. and Berglund, P. (2007) Trends Biotechnol., 25, 231.
55. White, M.C., Doyle, A.G., and Jacobsen, E.N. (2001) J. Am. Chem. Soc., 123, 7194.
56. Chen, K., Costas, M., Kim, J., Tipton, A.K., and Que, L. (2002) J. Am. Chem. Soc., 124, 3026
57. Bassan, A., Blomberg, M.R.A., Siegbahn, P.E.M., and Que, L. (2002) J. Am. Chem. Soc., 124, 11056, references cited therein.
58. Gelalcha, F.G., Bitterlich, B., Anikumar, G., Tse, M.K., and Beller, M. (2007) Angew. Chem. Int. Ed., 46, 7293-7296
59. Anilkumar, G., Bitterlich, B., Gelalcha, F.G., Tse, M.K., and Beller, M. (2007) Chem. Commun., 289-291.
60. Bitterlich, B., Schröder, K., Tse, M.K., and Beller, M. (2008) Eur. J. Org. Chem., 29, 4867-4867.
61. Schröder, K., Junge, K., Spannenberg, A., and Beller, M. (2010) Catal. Today, 157, 364-370
62. Schröder, K., Tong, X., Bitterlich, B., Tse, M.K., Gelacha, F.G., Brückner, A., and Beller, M. (2007) Tetrahedron Lett., 48, 6339-6339
63. Schröder, K., Enthaler, S., Bitterlich, B., Schulz, T., Spannenberg, A., Tse, M.K., Junge, K., and Beller, M. (2009) Chem. Eur. J., 15, 5471.
64. Hasan, K., Browne, N., and Kozak, C.M. (2011) Green Chem., 13, 1230.
65. Tse, M.K., Klawonn, M., Bhor, S., Döbler, C., Anilkumar, G., Hugl, H., Maegerlein, W., and Beller, M. (2005) Org. Lett., 7, 987-990.
66. For a review see: Mägerlein, W., Dreisbach, C., Hugl, H., Tse, M.K., Klawonn, M., Bhor, S., and Beller, M. (2007) Catal. Today, 121, 140-150.
67. Tse, M.K., Döbler, C., Bhor, S., Klawonn, M., Mägerlein, W., Hugl, H., and Beller, M. (2004) Angew. Chem. Int. Ed., 43, 5255
68. Tse, M.K., Bhor, S., Klawonn, M., Anilkumar, G., Jiao, H., Spannenberg, A., Döbler, C., Mägerlein, W., Hugl, H., and Beller, M. (2006) Chem. Eur. J, 12, 1855
69. Anilkumar, G., Bhor, S., Tse, M.K., Klawonn, M., Bitterlich, B., and Beller, M. (2005) Tetrahedron Asymm., 16, 3536-3561.
70. For a recent review see: Sgarbasso, P., Scarso, A., Strukul, G., and Michelin, R.N. (2012) Organometallics, 31, 1257-1278.
71. Colladon, M., Scarso, A., and Strukul, G. (2007) Adv. Synth. Catal., 349, 797-801.
72. See: Sheldon, R.A. and van Vliet, M.C.A. (2001) in Heterogeneous Catalysis for Fine Chemicals (eds R.A. Sheldon and H. van Bekkum), Wiley-VCH Verlag GmbH, Weinheim, pp. 473-490, and references cited therein.
73. Sato, T., Dakka, J., and Sheldon, R.A. (1994) Stud. Surf. Sci. Catal., 84, 1853-1860
74. Corma, A., Navarro, M.T., and Perez-Pariente, J. (1994) Chem. Commun., 147-148.
75. See http://www.chemicalstechnology. com/projects/BASF-HPPO (Last accessed 01.09.2012.).
76. Usui, Y., Sato, K., and Tanaka, M. (2003) Angew. Chem. Int. Ed., 42, 5623-5625.
77. Ansari, M.B., Jeong, E.Y., and Park, S.E. (2012) Green. Sustain. Chem., 2, 1-7.
78. Bortolini, O., Conte, V., DiFuria, F., and Modena, G. (1986) J. Org. Chem., 51, 2661.
79. Sato, K., Aoki, M., Takagi, J., and Noyori, R. (1997) J. Am. Chem. Soc., 119, 12386.
80. Sato, K., Takagi, J., Aoki, M., and Noyori, R. (1998) Tetrahedron Lett. 39, 7549.
81. Shi, X.Y. and Wei, J.F. (2005) J. Mol. Catal. A: Chem., 229, 13.
82. Haimov, A. and Neumann, R. (2006) J. Am. Chem. Soc., 128, 15697-15700.
83. Hamamoto, H., Suzuki, Y., Yamada, Y.M.A., Tabata, H., Takahashi, H., and Ikegami, S. (2005) Angew. Chem Int. Ed., 44, 4536
84. see also Ding, Y., Zhao, W., Zhang, Y., Ma, B., and Qiu, W. (2011) React. Kinet. Mech. Cat., 102, 92.
85. For excellent reviews see: Muzart, J. (2003) Tetrahedron, 59, 5789
86. Stahl, S.S. (2004) Angew. Chem. Int. Ed., 43, 3400.
87. Hintermann, L. (2004) in Transition Metals in Organic Synthesis (eds M. Beller and C. Bolm), Wiley-VCH Verlag GmbH, Weinheim, pp. 379-388
88. Monflier, E. and Mortreux, A. (2004) in Aqueous Phase Organometallic Chemistry, 2nd edn (eds B. Cornils and W. Herrmann), Wiley-VCH Verlag GmbH, Weinheim, pp. 481-487.
89. Papadogianakis, G., Verspui, G., Maat, L., and Sheldon, R.A. (1997) Catal. Lett., 47, 43.
90. ten Brink, G.J., Arends, I.W.C.E., and Sheldon, R.A. (2000) Science, 287, 1636.
91. ten Brink, G.J., Arends, I.W.C.E., and Sheldon, R.A. (2002) Adv. Synth. Catal., 344, 355.
92. Sheldon, R.A., Arends, I.W.C.E., and ten Brink, G.J. (2002) Acc. Chem. Res., 35, 774.
93. Stahl, S.S., Thorman, J.L., Nelson, R.C., and Kozee, M.A. (2001) J. Am. Chem. Soc., 23, 7188-7189
94. Steinhoff, B.A. and Stahl, S.S. (2002) Org. Lett., 4, 4179
95. Steinhoff, B.A., Fix, S.R., and Stahl, S.S. (2002) J. Am. Chem. Soc., 124, 766
96. Steinhoff, B.A., King, A.E., and Stahl, S.S. (2006) J. Org. Chem., 71, 1861-1868
97. Conley, N.R., Labios, L.A.B., Pearson, D.M., McCrory, C.M., and Waymouth, R.M. (2007) Organometallics, 26, 5447.
98. ten Brink, G.J., Arends, I.W.C.E., Hoogenraad, M., Verspui, G., and Sheldon, R.A. (2003) Adv. Synth. Catal., 345, 497.
99. ten Brink, G.J., Arends, I.W.C.E., Hoogenraad, M., Verspui, G., and Sheldon, R.A. (2003) Adv. Synth. Catal., 345, 1341.
100. Buffin, B.P., Belitz, N.L., and Verbeke, S.L. (2008) J. Mol. Catal. A: Chem., 284, 149-154
101. Buffin, B.P., Clarkson, J.P., Belitz, N.L., and Kundu, A. (2005) J. Mol. Catal. A: Chem., 225, 111-116.
102. Bailie, D.S., Clendenning, G.M.A., McNamee, L., and Muldoon, M.J. (2010) Chem. Commun, 7238-7240.
103. Kovtun, G., Kameneva, T., Hladyi, S., Starchevsky, M., Pazdersky, Y., Stolarov, I., Vargaftik, M., and Moiseev, I.I. (2002) Adv. Synth. Catal., 344 (9), 957-964
104. Moiseev, I.I. and Vargaftik, M.N. (1998) New J. Chem., 22, 1217-1227
105. Pasichnyk, P.I., Starchevsky, M.K., Pazdersky, Y.A., Zagorodnikov, V.P., Vargaftik, M.N., and Moiseev, I.I. (1994) Mendeleev Commun., 1-2
106. Moiseev, I.I., Stromnova, T.A., and Vargaftik, M.N. (1994) J. Mol. Catal., 86, 71-94.
107. Mifsud, M.M., Parkhomenko, K.V., Arends, I.W.C., and Sheldon, R.A. (2010) Tetrahedron, 66, 1040.
108. Prati, L. and Rossi, M. (1997) Stud. Surf. Sci. Catal., 110, 509
109. Prati, L. and Rossi, M. (1998) J. Catal., 176, 552
110. Bianchi, C., Porta, F., Prati, L., and Rossi, M. (2000) Top. Catal., 13, 231
111. Comotti, M., Della Pina, C., Matarrese, R., Rossi, M., and Siani, A. (2005) Appl. Catal. A: Gen., 291, 204-209
112. Prati, L. and Porta, F. (2005) Appl. Catal. A: General, 291, 199-203.
113. Abad, A., Concepcion, P., Corma, A., and Garcia, H. (2005) Angew. Chem. Int. Ed., 44, 4066-4069.
114. Christensen, C.H., Jørgensen, B., Rass-Hansen, J., Egeblad, K., Madfsen, R., Klitgaard, S.K., Hansen, S.M., Hansen, M.R., Andersen, H.C., and Riisager, A. (2006) Angew. Chem. Int. Ed., 45, 4648-4651.
115. Mori, K., Hara, T., Mizugaki, T., Ebitani, K., and Kaneda, K. (2004) J. Am. Chem. Soc., 126, 10657-10666.
116. Enache, D.I., Edwards, J.K., Landon, P., Solsona-Espriu, B., Carley, A.F., Herzing, A.A., Watanabe, M., Kiely, C.J., Knight, D.W., and Hutchings, G.J. (2006) Science, 311, 362-365.
117. Taarning, E., Nielsen, I.S., Egeblad, K., Madsen, R., and Christensen, C.H. (2008) ChemSusChem, 1, 75-78
118. see also Taarning, E., Madsen, A.T., Marchetti, J.M., Egeblad, K., and Christensen, C.H. (2008) Green Chem., 10, 408-414.
119. Biffis, A. and Minati, L. (2005) J. Catal., 236, 405-409
120. Biffis, A., Cunial, S., Spontoni, P., and Prati, L. (2007) J. Catal., 251, 1-6.
121. Tsunoyama, H., Sakurai, H., Negishi, Y., and Tsukuda, T. (2005) J. Am. Chem. Soc., 127, 9374-9375.
122. Miyamura, H., Matsubara, R., Miyazaki, Y., and Kobayashi, S. (2007) Angew. Chem. Int. Ed., 46, 4151-4154.
123. Uozumi, Y. and Nakao, R. (2003) Angew. Chem. Int. Ed., 42, 194-197
124. Uozumi, Y., Nakao, R., and Rhee, H. (2007) J. Organometal. Chem., 692, 420.
125. Yamada, Y.M.A., Arakawa, T., Hocke, H., and Uozumi, Y. (2007) Angew. Chem. Int. Ed., 46, 704-706.
126. Mertens, P.G.N., Vandezande, P., Ye, X., Poelman, H., De Vos, D.E., and Vankelecom, I.F.J. (2008) Adv. Synth. Catal., 350, 1241-1247.
127. Ma, Z., Yang, H., Qin, Y., Hao, Y., and Li, G. (2010) J. Mol. Catal. A: Chem., 331, 78.
128. Saio, D., Amaya, T., and Hirao, T. (2010) Adv. Synth. Catal., 352, 2177.
129. Komiya, N., Nakae, T., Sato, H., and Naota, T. (2006) Chem. Commun., 4829-4831.
130. Manyar, H.G., Chaure, G.S., and Kumar, A. (2006) Green Chem., 8, 344-348.
131. de Nooy, A.E.J., Besemer, A.C., and van Bekkum, H. (1996) Synthesis, 1153-1174.
132. Bragd, P.L., Besemer, A.C., and van Bekkum, H. (2001) J. Mol. Catal. A: Chem., 170, 35-42.
133. Bragd, P.L., van Bekkum, H., and Besemer, A.C. (2004) Top. Catal., 27, 49-66.
134. Golubev, V.A., Rozantsev, E.G., and Neiman, M.B. (1965) Bull. Acad. Sci. USSR, Chem. Ser., 14, 1898.
135. Cella, J.A., Kelley, J.A., and Kenehan, E.F. (1975) J. Org. Chem., 40, 1850
136. Rychovsky, S.D. and Vaidyanathan, R. (1999) J. Org. Chem., 64, 310.
137. Bolm, C., Magnus, A.S., and Hildebrand, J.P. (2000) Org. Lett., 2, 1173.
138. Kim, S.S. and Nehru, K. (2002) Synlett, 616.
139. Anelli, L., Biffi, C., Montanari, F., and Quici, S. (1987) J. Org. Chem., 52, 2559
140. see also Anelli, P., Banfi, S., Montanari, F., and Quici, S. (1989) J. Org. Chem., 54, 2970
141. Anelli, P.L., Montanari, F., and Quici, S. (1990) Org. Synth., 69, 212.
142. Ciriminna, R. and Pagliaro, M. (2010) Org. Proc. Res. Dev., 14, 245.
143. Pondelkina, I.Y., Khaibrakhmanova, E.A., and Odinokov, V.N. (2010) Russ. Chem. Rev., 79, 63.
144. Janssen, M.H.A., Chesa Castellana, J.F., Jackman, H., Dunn, P.J., and Sheldon, R.A. (2011) Green Chem., 13, 905.
145. Tanielyan, S.K., Augustine, R.L., Prakash, I., Furlong, K., and Jackson, H. (2006) in Catalysis of Organic Reactions, Chpter17 (ed. S.R. Schmidt), CRC Press, Boca Raton, pp. 141-146.
146. Dijksman, A., Arends, I.W.C.E., and Sheldon, R.A. (2000) Chem. Commun., 271.
147. Dijksman, A., Arends, I.W.C.E., and Sheldon, R.A. (2001) Synlett, 102.
148. Dijksman, A., Arends, I.W.C.E., and Sheldon, R.A. (2001) in Supported Catalysts and Their Applications (eds D.C. Sherrington and A.P. Kybett), Royal Society of Chemistry, pp. 118-124.
149. Weik, S., Nicholson, G., Jung, G., and Rademann, J. (2001) Angew. Chem. Int. Ed., 40, 1436.
150. Gilhespy, M., Lok, M., and Baucherel, X. (2006) Catal. Today, 117, 114.
151. See also Karimi, B., Biglari, A., Clark, J.H., and Budarin, V. (2007) Angew. Chem. Int. Ed., 46, 7210.
152. Qian, W., Jin, E., Bao, W., and Zhang, Y. (2006) Tetrahedron, 62, 556-562
153. Wu, X., Ma, L., Ding, M., and Gao, L. (2005) Synlett, 4, 607-610.
154. Sheldon, R.A. and Arends, I.W.C.E. (2004) Adv. Synth. Catal., 346, 1051-1107, and references cited therein.
155. Gamez, P., Arends, I.W.C.E., Reedijk, J., and Sheldon, R.A. (2003) Chem. Commun., 2414
156. Gamez, P., Arends, I.W.C.E., Sheldon, R.A., and Reedijk, J. (2004) Adv. Synth. Catal., 346, 805-811.
157. Mase, N., Mizumori, T., and Tatemoto, Y. (2011) Chem. Commun., 47, 2086.
158. Tohma, H., Maegawa, T., Takizawa, S., and Kita, Y. (2002) Adv. Synth. Catal., 344, 328-337.
159. Liu, Z.L., Yang, L., Mu, R., Liu, Z.Q., Yang, Z., and Liu, Z.G. (2005) Adv. Synth. Catal., 347, 1333.
160. Rochefort, D., Leech, D., and Bourbonnais, R. (2004) Green Chem., 6, 614.
161. Fabbrini, M., Galli, C., Gentili, P., and Macchitella, D. (2001) Tetrahedron Lett., 42, 7551.
162. Arends, I.W.C.E., Li, Y.X., Ausan, R., and Sheldon, R.A. (2006) Tetrahedron, 62, 6659
163. Tromp, S.A., Matijosyte, I., Sheldon, R.A., Arends, I.W.C.E., Mul, G., Kreutzer, M.T., Moulijn, J.A., and de Vries, S. (2010) ChemCatChem, 2, 827.
164. Arends, I.W.C.E., Li, Y.X., and Sheldon, R.A. (2006) Biocat. Biotrans., 24, 443.
165. Viikari, L., Niku-Paavola, M.L., Buchert, J., Forssell, P., Teleman, A., and Kruus, K. (1999) WO 992,324,0
166. Jetten, J.M., van den Dool, R.T.M., van Hartingsveldt, W., and van Wandelen, M.T.R. (2000) WO 00/50621.
167. Schoevaart, W.R.K., Van Langen, L.M., van den Dool, R.T.M., and Boumans, J.W.L. (2006) WO 2006/046865 A2, to CLEA Technologies.
168. Matijosyte, I., Arends, I.W.C.E., de Vries, S., and Sheldon, R.A. (2010) J. Mol. Catal. B: Enzymatic, 62, 142
169. for a recent review see: Sheldon, R.A. (2011) Org. Proc. Res. Dev, 15, 213.
170. Legros, J., Dehli, J.R., and Bolm, C. (2005) Adv. Synth. Catal., 347, 19-31, and references cited therein.
171. Prasanth, K.L. and Maheswaran, H. (2007) J. Mol. Catal. A: Chem., 268, 45, and references cited therein.
172. Sato, K., Hyodo, M., Aoki, M., Zheng, X.Q., and Noyori, R. (2001) Tetrahedron, 57, 2469.
173. Maity, P., Mukesh, D., Bhaduri, S., and Lahiri, G.K. (2009) J. Chem. Sci., 121, 377.
174. Federsel, H.J., Larrson, M. (2004) in Asymmetric Catalysis on Industrial Scale; Challenges, Approaches and Solutions (eds H.U. Blaser and E. Schmidt), Wiley-VCH Verlag GmbH, Weinheim, p. 413.
175. van Deurzen, M.P.J., Remkes, I.J., van Rantwijk, F., and Sheldon, R.A. (1997) J. Mol. Catal. A: Chem., 117, 329.
176. van Deurzen, M.P.J., van Rantwijk, F., and Sheldon, R.A. (1997) Tetrahedron, 53, 13183.
177. Leak, D.J., Sheldon, R.A., Woodley, J.M., and Adlercreutz, P. (2009) Biocat. Biotrans., 27, 1.
178. van Deurzen, M.P.J., Seelbach, K., van Rantwijk, F., Kragl, U., and Sheldon, R.A. (1997) Biocatal. Biotrans., 15, 1.
179. van de Velde, F., Lourenco, N.D., Bakker, M., van Rantwijk, F., and Sheldon, R.A. (2000,) Biotechnol. Bioeng., 69, 286.
180. Perez, D., van Rantwijk, F., and Sheldon, R.A. (2009) Adv. Synth. Catal., 351, 2133.
181. van de Velde, F., Arends, I.W.C.E., and Sheldon, R.A. (2000) J. Inorg. Biochem., 80, 81.
182. ten Brink, H.B., Tuynman, A., Dekker, H.L., Schoenmaker, H.E., and Wever, R. (1998) Eur. J. Biochem., 258, 906.
183. van de Velde, F., Könemann, L., van Rantwijk, F., and Sheldon, R.A. (1998) Chem. Commun., 1891.
184. van de Velde, F., Arends, I.W.C.E., and Sheldon, R.A. (2000) Top. Catal., 13, 259.
185. Rioz-Martinez, A., De Gonzalo, G., Torres Pazmino, D.E., Fraaije, M.W., and Gotor, V. (2010) Eur. J. Org. Chem., 6409.
186. Minidis, A.B.E. and Backvall, J.E. (2001) Chem. Eur. J., 7, 297.