Immobilization of organic catalysts: When, why, and how

Advanced Synthesis and Catalysis

Volumn 348, Issue 12-13, 2006, Pages 1367-1390

  Cozzi, Franco ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

Catalysis; Catalyst immobilization; Catalyst recovery and recycling; Organic catalysis; Organic synthesis; Stereoselective synthesis

Indexed keywords

EID: 33748257080     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200606096     Document Type: Review

References (136)

1. W. Langenbeck, Angew. Chem. 1928, 41, 740-745.
2. W. Langenbeck, Angew. Chem. 1931, 45, 97-99.
3. P. I. Dalko, L. Moisan, Angew. Chem. Int. Ed. 2004, 35, 5138-5175.
4. M. Benaglia, A. Puglisi, F. Cozzi, Chem. Rev. 2003, 103, 3401-3429.
5. G. Fu, Acc. Chem. Res. 2000, 33, 412-420.
6. S. E. Denmark, X. Su, Y. Nishiogaichi, D. M. Coe, K.-T. Wong, S. B. D. Winter, J. Y. Choi, J. Org. Chem. 1999, 64, 1958-1967; and references cited therein. The catalyst is obtained in five steps from l,2-diphenyl-l,2- diaminoethane.
7. T. Ooi, M. Kameda, K. Maruoka, J. Am. Chem. Soc. 2003, 125, 5139-5155. The catalyst is obtained in 8 steps from 1,1′-bi-2,2′-naphthol.
8. R. Breslow, Science 1982, 218, 532-537.
9. Acc. Chem. Res. 2004, 37, issue 8.
10. Adv. Synth. Catal. 2004, 346, issue 8/9.
11. A. Berkessel, H. Groger, in: Asymmetric Organic Catalysis, Wiley VCH, Weinheim, 2005.
12. R. I. Storer, D. E. Carrera, Y. Ni, D. W. C. MacMillan, J. Am. Chem. Soc. 2006, 128, 84-86.
13. Enzyme Catalysis in Organic Synthesis: A Comprehensive Handbook, Vol. 3, 2nd edn., (Eds.: K. Drauz, H. Waldmann), Wiley-VCH, Weinheim, 2002
14. . For a recent collection of articles on biocatalysis see: Adv. Synth. Catal. 2003, 345, issue 6/7;
15. see also: C. R. Martin, P. Kohli, Nature Review Drug Discovery 2003, 2, 29-37;
16. A.-X. Yan, X.-W. Li, Y.-H. Ye, Appl. Biochem. Biotech. 2002, 101, 113-129.
17. For the immobilization of mostly organometallic catalysts see: D. E. De Vos, I. F. J. Vankelecom, P. A. Jacobs, in: Chiral Catalysts Immobilization and Recycling, Wiley-VCH, Weinheim, 2000.
18. Chem. Rev. 2002, 102, issue 10.
19. Bioorg. Med. Chem. Lett. 2002, 12, issue 14.
20. For a review on microencapsulation see : S. Kobayashi, R. Akiyama, Chem. Commun. 2003, 449-460.
21. For recent applications of ionic polymers see: B. S. Lee, S. Mahajan, K. D. Janda, Tetrahedron Lett. 2005, 46, 807-810 and 4491-4493.
22. For a very remarkable exception in which the development of the immobilized catalyst preceeded and was crucial to that of the non-supported one see: a) M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 4901-4902;
23. b) M. S. Sigman, P. Vachal, E. N. Jacobsen, Angew. Chem. Int. Ed. 2000, 39, 1279-1281;
24. c) P. Vachal, E. N. Jacobsen, J. Am. Chem. Soc. 2002, 124, 10012-10014. (See section 4.2 for a discussion of this example.)
25. R. A. Sheldon, I. W. C. E. Arends, Adv. Synth. Catal. 2004, 346, 1051-1071.
26. T. Fey, H. Fischer, S. Bachmann, K. Albert, C. Bolm, J. Org. Chem. 2001, 66, 8154-8159.
27. A. Dijksman, I. W. C. E. Arends, R. A. Sheldon, Chem. Commun. 2000, 271-272.
28. See also: A. Dijksman, I. W. C. E. Arends, R. A. Sheldon, Synlett 2001, 102-104.
29. G. Pozzi, M. Cavazzini, S. Quici, M. Benaglia, G. Dell' Anna, Org. Lett. 2004, 6, 441-443.
30. For another example of soluble polymer supported TEMPO see: C. Tanyeli, A. Gümüş, Tetrahedron Lett. 2003, 44, 1639-1642. This catalyst was shown to be less efficient than the PEG-TEMPOs here described.
31. P. Ferreira, E. Phillips, D. Rippon, S. C. Tsang, W. Hayes, J. Org. Chem. 2004, 69, 6851-6859.
32. For the previous use of a similar spacer in combination with PEG see: M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Tetrahedron Lett. 2002, 43, 3391-3393.
33. The importance of the role of the spacer in polymer supported catalysis was first demonstrated in the case of phase-transfer catalysts anchored to a polystyrene matrix: P. L. Anelli, B. Czech, F. Monatanari, S. Quici, J. Am. Chem. Soc. 1984, 106, 861-869; and references cited therein.
34. M. Benaglia, A. Puglisi, O. Holczknecht, S. Quici, G. Pozzi, Tetrahedron 2005, 61, 12058-12064.
35. F. Minisci, F. Recupero, A. Cecchetto, C. Gambarotti, C. Punta, R. Faletti, R. Paganelli, G. Pedulli, Eur. J. Org. Chem. 2004, 109-119; and references cited therein.
36. M. Gilhespy, M. Lok, X. Baucherel, Chem. Commun. 2005, 1085-1086.
37. T. Y. S. But, Y. Tashino, H. Togo, P. H. Toy, Org. Biomol. Chem. 2005, 3, 970-971.
38. P. H. Toy, K. D. Janda, Tetrahedron Lett. 1999, 40, 6329-6332.
39. H. Togo, K. Sakuratani, Synlett 2002, 1966-1975.
40. For a general review on the use of dioxiranes see: a) R. W. Murray, Chem. Rev. 1989, 89, 1187-1201;
41. for dioxirane-mediated enantioselective alkene epoxidation see: b) S. E. Denmark, Z. Wu, Synlett 1999, 847-859.
42. K. Neimann, R. Neumann, Chem. Commun. 2001, 487-488.
43. J. T. W. Kan, P. H. Toy, Tetrahedron Lett. 2004, 45, 6357-6359.
44. A. Masuyama, T. Yamaguchi, M. Abe, M. Nojima, Tetrahedron Lett. 2005, 46, 213-216.
45. A. C. Spivey, S. Arseniyadis, Angew. Chem. Int. Ed. 2004, 43, 5436-5441; and references cited therein.
46. M. Tomoi, Y. Akada, H. Kakiuchi, Makromol. Chem. Rapid Commun. 1982, 3, 537-542.
47. D. Basavaiah, A. J. Rao, T. Satyanarayana, Chem. Rev. 2003, 103, 811-891.
48. A. Corma, H. Garcia, A. Leyva, Chem. Commun. 2003, 2806-2807.
49. J.-W. Huang, M. Shi, Adv. Synth. Catal. 2003, 345, 953-958.
50. H.-T. Chen, S. Hu, J. W. Wiench, M. Pruski, V. S.-Y. Li, J. Am. Chem. Soc. 2005, 127, 13305-13311.
51. D. E. Bergbreiter, Chem. Rev. 2002, 102, 3345-3383.
52. D. E. Bergbreiter, P. L. Osburn, T. Smith, C. Li, J. D. Frels, J. Am. Chem. Soc. 2003, 125, 6254-6260.
53. See also: J. Li, S. Sung, J. Tian, D. E. Bergbreiter, Tetrahedron 2005, 61, 12081-12092.
54. D. E. Bergbreiter, C. Li, Org. Lett. 2003, 5, 2445-2447.
55. The polystyyrene-supported version of triphenylphosphine is commercially available: M. Bernard, W. T. Ford, J. Org. Chem. 1983, 48, 326-332.
56. L.-J. Zhao, C. K.-W. Kwong, M. Shi, P. H. Toy, Tetrahedron 2005, 61, 12026-12032.
57. D. Bensa, T. Constantieux, J. Rodriguez, Synthesis 2004, 923-927.
58. G. Wulff, Chem. Rev. 2002, 102, 1-27; and references cited therein.
59. K. Manabe, S. Kobayashi, Adv. Synth. Catal. 2002, 344, 270-273.
60. S. Iimura, K. Manabe, S. Kobayashi, Org. Lett. 2003, 5, 101-103.
61. S. Iimura, K. Manabe, S. Kobayashi, Org. Biomol. Chem. 2003, 1, 2416-2418.
62. [4] and K Ishiara, A. Hasegawa, H. Yamamoto, Angew. Chem. Int. Ed. 2001, 40, 4077-4081.
63. T. Aoyama, T. Takido, M. Kodomari, Synlett 2004, 2307-2310.
64. Y.-S. Hon, C.-F. Lee, R.-J. Chen, Y.-F. Huang, Synth. Comm. 2003, 33, 2829-2842.
65. R. Breslow, J. Am. Chem. Soc. 1958, 80, 3719-3726.
66. H. Stetter, H. Kuhlmann, Org. React. 1991, 40, 407-496.
67. a) C. S. Sell, L. A. Dorman, Chem. Commun. 1982, 629-630;
68. b) T. L. Ho, S.-H. Liu, Synth. Comm. 1983, 13, 1125-1127;
69. c) K. Karimian, F. Mohanazadeh, S. Rezai, 1983, 20, 1119-1121;
70. d) H. J. Van der Berg, G. Challa, U. K. Pandit, J. Mol. Catal. 1989, 51, 13-27.
71. A. G. M. Barrett, A. C. Love, L. Tedeschi, Org. Lett. 2004, 6, 3377-3380.
72. K.-S. Kim, J.-H. Kim, G. Seo, Chem. Commun. 2003, 372-373.
73. M. Benaglia, T. Danelli, F. Fabris, D. Sperandio, G. Pozzi, Org. Lett. 2002, 4, 4229-4242.
74. C. J. Rogers, T. J. Dickerson, P. Wentworth, K. D. Janda, Tetrahedron 2005, 61, 12140-12144.
75. S. Hung, H.-T. Chen, J. W. Wiench, M. Pruski, V. S.-Y. Lin, Angew. Chem. Int. Ed. 2005. 44, 1826-1830;
76. and references cited therein. For a related study see: S. Hung, H.-T. Chen, J. W. Wiench, M. Pruski, V. S.-Y. Lin, J. Am. Chem. Soc. 2004, 126, 1010-1011.
77. For a recent report on the use of a silica-supported mono-functional amino catalyst for the aldol self-condensation of aldehydes see: H. Hagiwara, J. Hamaya, T. Hoshi, C. Yokoama, Tetrahedron Lett. 2005, 46, 393-395.
78. G. Sartori, A. Armstrong, R. Maggi, A. Mazzacani, R. Sartorio, F. Bigi, B. Domingúez-Fernandez, J. Org. Chem. 2003, 68, 3232-3237.
79. L. Shu, P. Wang, Y. Can, Y. Shi , Org. Lett. 2003, 5, 293-296; and references cited therein.
80. Unpublished results from the author's laboratories.
81. M. J. Porter, J. Skidmore, Chem. Commun. 2000, 1215-1225; and references cited therein.
82. S. B. Tsogoeva, J. Wöltinger, C. Jost, D. Reichert, A. Künle, H. P. Krimmer, K. Drauz, Synlett 2002, 707-710.
83. D. R. Kelly, T. T. T. Bui, E. Caroff, A. F. Drake, S. M. Roberts, Tetrahedron Lett. 2004, 45, 3885-3888.
84. G. Priem, B. Pelotier, S. J. F. Macdonald, M. S. Anson, I. B. Campbell, J. Org. Chem. 2003, 68, 3844-3848.
85. G. Priem, B. Pelotier, S. J. F. Macdonald, M. S. Anson, I. B. Campbell, Synlett 2003, 679-683.
86. For an example of recyclable, polystyrene-supported, chiral acylating reagent for the kinetic resolution of amines see: S. Arseniyadis, P. V. Subhash, A. Valleix, A. Wagner, C. Mioskowski, Chem. Commun. 2005, 3310-3312.
87. a) S. E. Denmark, J. Fu, M. J. Lawler, J. Org. Chem. 2006, 71, 1523-1536;
88. S. E. Denmark, J. Fu, D. M. Coe, X. Su, N. E. Pratt, B. D. Griedel, J. Org. Chem. 2006, 71, 1513-1522; and references cired therein;
89. b) S. E. Denmark, T. Bui, J. Org. Chem. 2005, 70, 10393-10399.
90. T. Oyama, H. Yoshioka, M. Tomoi, Chem. Commun. 2005, 1857-1859.
91. For examples of poorly efficient achiral supported organocatalysts for this allylation reaction see: a) C. Ogawa, M. Suigura, S. Kobayashi, Chem. Commun. 2003, 192-193;
92. b) R. A. Flowers, X. Xu, C. Timmons, G. Li, Eur. J. Org. Chem. 2004, 2988-2990.
93. For a recent study describing the determination of site-site distance and site concentration within polymer beads of different polystyrene-type polymers see: R. Marchetto, E. M. Cilli, G. N. Jubilut, S. Schreier, C. R, Nakaie, J. Org. Chem. 2005, 71, 4561-4568.
94. For a review on the use of Cinchona alkaloids as organic catalysts see: K. Kacprzak, J. Gawronski, Synthesis 2001, 961-998.
95. [4].
96. B. Thierry, J.-C. Plaquevent, D. Cahard, Tetrahedron: Asymmetry 2003, 14, 1671-1677.
97. M. J. O'Donnell, Aldrichimica Acta 2001, 34, 3-15; and references cited therein.
98. See for instance: a) R. Alvarez, M.-A. Hourdin, C. Cave, J. D'Angelo, P. Chaminade, Tetrahedron Lett. 1999, 40, 7091-7094;
99. b) B. Thierry, J.-C. Plaquevent, D. Cahard, Tetrahedron: Asymmetry 2001, 12, 983-986.
100. [4]
101. 5000: a) M. Benaglia, M. Cinquini, F. Cozzi, A. Puglisi, G. Celentano, Adv. Synth. Catal. 2002, 344, 533-542;
102. b) M. Benaglia, M. Cinquini, F. Cozzi, A. Puglisi, G. Celentano, J. Mol. Catal. A: Chemical 2003, 204-205, 157-163.
103. Proline supported on 1% cross-linked polystyrene: a) K. Kondo, T. Yamano, K. Takemoto, Makromol. Chem. 1985, 186, 1781-1785;
104. proline supported on silica gel column: b) K. Sakthivel, W. Notz, T. Bui, C. F. Barbas, J. Am. Chem. Soc. 2001, 123, 5260-5267;
105. for a more recent example of proline immobilized on silica gel see: c) Z. Shen, C. Jiao, Y. Ding, J. Ma, J. Gu, Y. Zhang, Huaxue Yanjiu 2005, 16, 22-25. This recyclable catalyst promotes the aldol condensation of acetone with benzaldehyde in 86% ee.
106. a) G. Szöllosi, G. London, L. Balàspiri, C. Somlai, M. Bartòk, Chirality 2003, 15, S90-S96
107. . For a recent report demonstrating the efficiency of prolinamides as organic catalysts see: b) 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.
108. Z. Shen, Y. Liu, C. Jiao, J. Ma, M. Li, Y. Zhang, Chirality 2005, 17, 556-558.
109. a) F. Calderòn, R. Fernandez, F. Sanchez, A. Fernandez-Mayoralas, Adv. Synth. Catal. 2005, 347, 1395-1403;
110. for a previous similar report see: b) D. Dhar, I. Eadham, S. Chandrasekaran, Proc. Ind. Acd. Sci. (Chem. Sci.), 2003, 365-372.
111. K. A. Ahrendt, C. J. Berths, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 4243-4244.
112. M. Benaglia, G. Celentano, M. Cinquini, A. Puglisi, F. Cozzi, Adv. Synth. Catal. 2002, 344, 149-152.
113. S. A. Selkälä, J. Tois, P. M. Pihko, A. M. P. Koskinen, Adv. Synth. Catal. 2002, 344, 941-945.
114. M. Benaglia, G. Celentano, M. Cinquini, A. Puglisi, F. Cozzi, Eur. J. Org. Chem. 2004, 567-573.
115. W. S. Jen, J. J. M. Wiener, D. W. C. MacMillan, J. Am. Chem. Soc. 2000, 122, 9874-9875.
116. As pointed out by one of the referees not necessarily catalyst recycling is a major goal per se. Indeed, industries working under strict GMP conditions might be attracted by catalyst recycling if and only if it has been scrupulously proved that the recycled catalyst does indeed display the same level of activity as the fresh catalyst.
117. D. J. Gravert, K. D. Janda, Chem. Rev. 1997, 97, 489-509;
118. P. Wentworth, K. D. Janda, Chem. Commun. 1999, 1917-1924.
119. For examples of organocatalyzed reactions carried out under the continuous flow mode see: a) K. Ishiara, A. Hasegawa, H. Yamamoto, Synlett 2002, 1296-1298;
120. b) M. Brünjes, G. Sourkouni-Argirusi, A. Kirschning, Adv. Synth. Catal. 2003, 345, 635-642;
121. for a review on continuous flow methods see: c) G. Jas, A. Kirschning, Chem. Eur. J. 2003, 9, 5708-5723.
122. The Aldrich catalog, 2005-2006 edition.
123. M. S. Sigman, E. N. Jacobsen, J. Am. Chem. Soc. 1998, 120, 5315-5316.
124. For pioneering work on how an increased loading of active sites does not necessarily corresponds to increased catalytic activity see: P. L. Anelli, F. Montanari, S. Quici, J. Org. Chem. 1986, 51, 4910-4914; and references cited therein.
125. R. Annunziata, M. Benaglia, M. Cinquini, F. Cozzi, G. Tocco, Org. Lett. 2000, 2, 1737-1739.
126. For the beneficial effect exerted on the phase-transfer catalytic activity by the insertion of PEG fragment between an insoluble polystyrene matrix and quaternary ammonium salt residues see: K. Shibatomi, T. Nakahashi, Y. Uozumi, Synlett 2000, 1643-1645.
127. H. Molinari, F. Monatanari, S. Quici, P. Tundo, J. Am. Chem. Soc. 1979, 101, 3920-3927.
128. [4]
129. [80]
130. T. Balakrishnan, E. Murugan, J. Polym. Sc., Part A: Polym. Chem. 2003, 41, 347-364.
131. After the completion of this review the following articles appeared in the literature on the subject of immobilized organic catalysts: a) proline: M. R. M. Andreae, A. P. Davis, Tetrahedron: Asymmetry 2005, 16, 2487-2492;
132. b) Cinchona alkaloids: D. Bernstein, S. France, J. Wolfer, T. Lectka, Tetrahedron: Asymmetry 2005, 16, 3841-3843;
133. c) dicyanoketene acetals: Y. Masaki, T. Yamada, H. Kawai, A. Itoh, Y. Arai, H. Furukawa, Synlett 2006, 288-290;
134. d) quaternary ammonium salts: Y. Du, J.-Q. Wang, J.-Y. Chen, F. Cai, J.-S. Tian, D.-L. Kong, L.-N. He, Tetrahedron Lett. 2006, 47, 1271-1275;
135. e) phosphonium salts: T. Takahashi, T. Watahiki, S. Kitazume, H. Yasuda, T. Sakakura, Chem. Commun. 2006, 1664-1666;
136. f) bifunctional amine and sulfonic acid: N. T. S. Phan, C. S. Gill, J. V. Nguyen, Z. J. Zhang, C. W. Jones, Angew. Chem. Int. Ed. 2006, 45, 2209-2212.