Green Catalysis
Kiyotomi Kaneda,
Tomoo Mizugaki,
Takato Mitsudome,
Kiyotomi Kaneda
Research Center for Solar Energy Chemistry, Osaka University, Toyonaka, Osaka, Japan
Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka, Japan
Search for more papers by this authorTomoo Mizugaki
Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka, Japan
Search for more papers by this authorTakato Mitsudome
Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka, Japan
Search for more papers by this authorKiyotomi Kaneda,
Tomoo Mizugaki,
Takato Mitsudome,
Kiyotomi Kaneda
Research Center for Solar Energy Chemistry, Osaka University, Toyonaka, Osaka, Japan
Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka, Japan
Search for more papers by this authorTomoo Mizugaki
Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka, Japan
Search for more papers by this authorTakato Mitsudome
Department of Materials Engineering Science, Graduate School of Engineering Science, Osaka University, Toyonaka, Osaka, Japan
Search for more papers by this authorFirst published: 15 September 2010
Abstract
This article is an introduction to catalysis for green sustainable chemistry emphasizing typical examples of important catalytic processes. Green catalysis is discussed in relation to heterogeneous catalyses that mainly target solid acid and base catalyses for the synthesis of fine chemicals.
Bibliography
- 1(a) P. T. Anastas and T. C. Williamson, eds., Green Chemistry, Oxford University Press, 1998; (b) J. H. Clark, Green Chem. 1, 1 (1999); (c) J. H. Clark, Green Chem. 8, 17 (2006).
- 2 http://www.epa.gov/greenchemistry/pubs/principles.html.
- 3 B. M. Trost, Angew. Chem. Int. Ed. Engl. 34, 259 (1995).
- 4 R. A. Sheldon, Pure Appl. Chem. 72, 1233 (2000).
- 5 K. Tanabe and W. F. Hoelderich, Appl. Catal. A. 181, 399 (1999).
- 6 G. Busca, Chem. Rev. 107, 5366 (2007).
- 7 J. N. Armor, Appl. Catal. 78, 141 (1991).
- 8 N. Nojiri and M. Misono, Appl. Catal. A. 93, 103 (1993).
- 9 P. T. Anastas and T. C. Williamson, Green Chemistry: Theory and Practice, Oxford University Press, 1998.
- 10 H. Ishida, Catal. Surve. Jpn. 1, 241 (1997).
- 11 Y. Izumi, K. Hisano, and T. Hida, Appl. Catal. A. 181, 277 (1999).
- 12 A. Benito, A. Corma, H. García, and J. Primo, Appl. Catal. A 116, 127 (1997).
- 13 M. Misono and N. Nojiri, Appl. Catal. 64, 1 (1990).
- 14 G. A. Olah, T. Shamma, and G. K. S. Prakash, Catal. Lett. 46, 1 (1997).
- 15 W. F. Hoelderich and D. Heinz, Res. Chem. Intermed. 24, 337 (1998).
- 16 H. Hattori, Stud. Surf. Sci. Catal. 77, 69 (1993).
- 17 T. Okuhara and T. Nakato, Catal. Surve. Jpn. 2, 31 (1998).
- 18 K. Kaneda, Synlett 7, 999 (2007).
- 19 A. E. W. Beers, T. A. Nijhuis, F. Kapteijn, in R. A. Sheldon, H. Bekkum eds., Fine Chemicals through Heterogeneous Catalysis, Wiley-VCH, Weinheim, 2000, pp. 116–120.
- 20 M. Hara, Chem Sus Chem. 2, 129 (2009).
- 21 A. Corma and H. Garcia, Catal. Today 38, 257 (1997).
- 22 G. A. Olah, Friedel-Crafts and Related Reactions, Vol. 3, Part 1. Wiley-Interscience, New York, (1964).
- 23 J. Kaur and I. V. Kozhevnikov, Chem. Commun. 2508 (2002).
- 24 O. L. Wang, Y. Ma, X. Ji, H. Yan, and Q. Qiu, J. Chem. Soc. Chem. Commun. 2307 (1995).
- 25 B. Chiche, A. Finiels, C. Gauthier, and P. Geneste, J. Mol. Catal. 42, 229 (1987).
- 26 K. Ebitani, M. Kato, K. Motokura, T. Mizugaki, and K. Kaneda, Res. Chem. Intermed. 32, 305 (2006).
- 27 M. Hino and K. Arata, J. Chem. Soc. Chem. Commun. 112 (1985).
- 28 P. Laszlo, Science 235, 1473 (1987).
- 29 T. J. Pinnavaia, Science 220, 365 (1983).
- 30 J. H. Clark and D. J. Macquarrie, Chem. Soc. Rev. 25, 303 (1996).
- 31 Y. Izumi and M. Onaka, Adv. Catal. 38, 245 (1992).
- 32 P. Laszlo, Acc. Chem. Res. 19, 121 (1986).
- 33(a) M. Noji, T. Ohno, K. Fuji, N. Futaba, H. Tajima, and K. Ishii, J. Org. Chem. 68, 9340 (2003); (b) V. Terrasson, S. Marque, M. Georgy, J.-M. Campagne, and D. Prim, Adv. Synth. Catal. 348, 2063 (2006).
- 34(a) F. Bisaro, G. Prestat, M. Vitale, and G. Poli, Synlett 11, 1823 (2002); (b) G. C. Gullickson and D. E. Lewis, Aust. J. Chem. 56, 385 (2003); (c) M. Yasuda, T. Somyo, and A. Baba, Angew. Chem., Int. Ed. 45, 793 (2006); (d) R. Sanz, A. Martínez, D. Miguel, J. M. Álvarez-Gutiérrez, and F. Rodríguez, Adv. Synth. Catal. 348, 1841 (2006).
- 35(a)
J. A. Cella,
J. Org. Chem.
47,
2125
(1982);
(b)
G. Kaur,
M. Kaushik, and
S. Trehan,
Tetrahedron Lett.
38,
2521
(1997);
(c)
A. Schmitt and
H.-U. Reißig,
Eur. J. Org. Chem.
2000,
3893
(2000);
10.1002/1099-0690(200012)2000:23<3893::AID-EJOC3893>3.0.CO;2-E Google Scholar(d) M. Rubin and V. Gevorgyan, Org. Lett. 3, 2705 (2001); (e) M. Yasuda, T. Saito, M. Ueba, and A. Baba, Angew. Chem., Int. Ed. 43, 1414 (2004); (f) G. V. M. Sharma, K. L. Reddy, P. S. Lakshmi, R. Ravi, and A. C. Kunwar, J. Org. Chem. 71, 3967 (2006).
- 36 K. Motokura, N. Fujita, K. Mori, T. Mizugaki, K. Ebitani, and K. Kaneda, J. Am. Chem. Soc. 127, 9674 (2005).
- 37 Brønsted acid catalysis: (a) K. Ebitani, T. Kawabata, K. Nagashima, T. Mizugaki, and K. Kaneda, Green Chem. 2, 157 (2000); Lewis acid catalysis: (b) T. Kawabata, T. Mizugaki, K. Ebitani, and K. Kaneda, J. Am. Chem. Soc. 125, 10486 (2003); (c) T. Kawabata, M. Kato, T. Mizugaki, K. Ebitani, and K. Kaneda, Chem. Eur. J. 11, 288 (2005).
- 38 K. Motokura, N. Fujita, K. Mori, T. Mizugaki, K. Ebitani, and K. Kaneda, Angew. Chem., Int. Ed. 45, 2605 (2006); (b) K. Motokura, N. Nakagiri, K. Mori, T. Mizugaki, K. Ebitani, K. Jitsukawa, and K. Kaneda, Org. Lett. 8, 4617 (2006).
- 39 M. J. Howard, G. J. Sunley, A. D. Poole, R. J. Watte, and B. K. Sharma, Stud. Surf. Sci. Catal. 121, 61 (1999).
- 40 T. Okuhara and N. Mizuno, Adv. Catal. 41, 113 (1996).
- 41 R. E. Gawley, Org. React. 35, 1 (1988).
- 42 Y. Izumi, H. Ichihashi, Hiroshi; Y. Shimazu, M. Kitamura, and H. Sato, Bull. Chem. Soc. Jpn. 80, 1280 (2007).
- 43 S. Miyata, Clays Clay Miner. 23, 369 (1975).
- 44 S. Miyata, Clays Clay Miner. 28, 50 (1980).
- 45 F. Cavani, F. Trifiro, and A. Vaccari, Catal. Today 11, 173 (1991).
- 46 K. Ebitani, K. Motokura, K. Mori, T. Mizugaki, and K. Kaneda, J. Org. Chem. 71, 5440 (2006).
- 47 D. Ticht, M. H. lhouty, A. Guida, B. Chiche, F. Figueras, A. Auroux, D. Bartalini, and E. Garrone, J. Catal. 151, 50 (1995).
- 48 G. Jones, Org. React. 15, 204 (1967).
- 49 L. Knoevenagel, Ber. 31, 258 (1898).
- 50 A. Corma and S. Iborra, in R. A. Sheldone and H. Bekkum, eds., Fine Chemicals through Heterogeneous Catalysis, Wiley-VCH, Weinheim, 2001, p. 309.
- 51 A. Corma, V. Fornes, R. M. Martin-Aranda, and F. Rey, J. Catal. 134, 58 (1992).
- 52 T. Hara, K. Mori, T. Mizugaki, K. Ebitani, K. Jitsukawa, and K. Kaneda, J. Org. Chem. 71, 7455 (2006).
- 53 A. Angeletti, C. Canepa, G. Martinetti, and P. Venturello, Tetrahedron Lett. 29, 2261 (1988).
- 54 E. D. Bergmann, D. Ginsburg, and R. Pappo, Org. React. 10, 179 (1959).
- 55 J. H. Clark and D. G. Cork, Chem. Lett. 26, 2645 (1985).
- 56 H. Kabashima, H. Tsuji, and H. Hattori, Appl. Catal. A 165, 319 (1997).
- 57 J. E. Mcmurry and J. Melton, J. Org. Chem. 38, 436 (1973).
- 58(a) R. A. Sheldon, Chem. Commun. 3352 (2008); (b) H. Fujiwara, Y. Ogasawara, K. Yamaguchi, and N. Mizuno, Angew. Chem. Int. Ed. 46, 5202 (2007); (c) H. R. Shaterian, H. Yarahmadi, and M. Ghashang, Tetrahedron 64, 1263 (2008); (d) H. Sharghi, M. H. Beyzavi, and M. M. Doroodmand, Eur. J. Org. Chem. 2008, 4126 (2008); (e) X. Zeng, G. D. Frey, S. Kousar, and G. Bertrand, Chem. Eur. J. 15, 3056 (2009).
- 59 B. Voit, Angew. Chem. Int. Ed. 45, 4238 (2006).
- 60(a) T. D. Nixon, M. K. Whittlesev, and J. M. J. Williams, Dalton Trans. 38, 753 (2009); (b) M. H. S. A. Hamid, P. A. Slatford, and J. M. J. Williams, Adv. Synth. Catal. 349, 1555 (2007); (c) G. Guillena, D. J. Ramon, and M. Yus, Angew. Chem. Int. Ed. 46, 2358 (2007).
- 61 K. Motokura, D. Nishimura, K. Mori, T. Mizugaki, K. Ebitani, and K. Kaneda, J. Am. Chem. Soc. 126, 5662 (2004).
- 62 R. W. Hartmann and C. Batzl, J. Med. Chem. 29, 1362 (1986).
- 63(a)
F. Gelman,
J. Blum, and
D. Avnir,
New J. Chem.
27,
205
(2003);
(b)
F. Gelman,
J. Blum, and
D. Avnir,
Angew. Chem., Int. Ed.
40,
3647
(2001);
10.1002/1521-3773(20011001)40:19<3647::AID-ANIE3647>3.0.CO;2-A CAS PubMed Web of Science® Google Scholar(c) F. Gelman, J. Blum, and D. Avnir, J. Am. Chem. Soc. 122, 11999 (2000).
- 64 T. Kawabata, T. Mizugaki, K. Ebitani, and K. Kaneda, Tetrahedron Lett. 42, 8329 (2001).
- 65 T. Kawabata, T. Mizugaki, K. Ebitani, and K. Kaneda, Tetrahedron Lett. 44, 9205 (2003).
- 66 K. Yamaguchi, K. Mori, T. Mizugaki, K. Ebitani, and K. Kaneda, J. Org. Chem. 65, 6897 (2000).
