Iron(III)-zirconium(IV) combined salt immobilized on N-(polystyrylbutyl) pyridinium triflylimide as a reusable catalyst for a dehydrative esterification reaction

Advanced Synthesis and Catalysis

Volumn 348, Issue 12-13, 2006, Pages 1505-1510

  Nakamura, Yuka ^a   Maki, Toshikatsu ^a   Wang, Xiaowei ^a   Ishihara, Kazuaki ^a,b   Yamamoto, Hisashi ^b  

^a NAGOYA UNIVERSITY   (Japan)

^b UNIVERSITY OF CHICAGO   (United States)

Author keywords

Dehydration; Esterification; Esters; Green chemistry; Ionic liquids; Recycling catalyst

Indexed keywords

EID: 33748270464     PISSN: 16154150     EISSN: 15213897     Source Type: Journal    
DOI: 10.1002/adsc.200606126     Document Type: Article

References (24)

1. a) K. Ishihara, S. Ohara, H. Yamamoto, Science 2000, 290, 1140-1142;
2. b) K. Ishihara, M. Nakayama, S. Ohara, H. Yamamoto, Synlett 2001, 1117-1120;
3. c) K. Ishihara, M. Nakayama, S. Ohara, H. Yamamoto, Tetrahedron 2002, 58, 8179-8188;
4. d) M. Nakayama, A. Sato, K. Ishihara, H. Yamamoto, Adv. Synth. Catal. 2004, 346, 1275-1279;
5. e) A. Sato, Y. Nakamura, T. Maki, K. Ishihara, H. Yamamoto, Adv. Synth. Catal. 2005, 347, 1337-1340.
6. For the immobilization of ionic liquids on solid supports, see: a) M. H. Valkenberg, C. deCastro, W. F. Hölderich, Green Chem. 2002, 4, 88-93;
7. b) A. Wolfson, I. F. J. Vankelecom, P. A. Jacobs, Tetrahedron Lett. 2003, 44, 1195-1198;
8. c) B. S. Lee; S. Mahajan, K. D. Janda, Tetrahedron Lett. 2005, 46, 807-810;
9. d) B. S. Lee; S. Mahajan, K. D. Janda, Tetrahedron Lett. 2005, 46, 4491-4493;
10. e) S. Miao, Z. Liu, B. Han, J. Huang, Z. Sun, J. Zhang, T. Jiang, Angew. Chem. Int. Ed. 2006, 45, 266-269;
11. f) B. Karimi, D. Enders, Org. Lett. 2006, 8, 1237-1240.
12. For immobilized ammonium sulfonate catalysts for dehydrative esterification reactions, see: a) K. Ishihara, S. Nakagawa, A. Sakakura, J. Am. Chem. Soc. 2005, 127, 4168-4169;
13. b) A. Sakakura, S. Nakagawa, K. Ishihara, Tetrahedron 2006, 62, 422-433.
14. For a review for microcapsulated catalysts, see: S. Kobayashi, R. Akiyama, Chem. Commun. 2003, 449-460. According to Kobayashi et al. metal species of microcapsulated catalysts are strongly immobilized by physical envelopment by polymer backbones and interaction between π electrons of benzene rings of the polystyrenes used as polymer backbones and vacant orbitals of the metal species. Therefore, the metal species are not released from polymer backbones even during the catalysis.
15. 4], see: a) S. Hayashi, H. Hamaguchi, Chem. Lett. 2004, 33, 1590-1591
16. and S. Hayashi, H. Hamaguchi, Chem. Lett. 2005, 34, 740 (additions and corrections);
17. b) T. Sasaki, C. Zhong, M. Tada, Y. Iwasawa, Chem. Commun. 2005, 2506-2508, and references therein.
18. For examples of Zr(IV)-Fe(III) combined complexes, see: a) A. Shah, A. Singh, R. C. Mehrotra, Ind. J. Chem. 1987, 26A, 485-488;
19. b) S. S. Berdonosov, B. I. Kharisov, I. V. Melikhov, Zh. Neorganicheskoi Khimii 1988, 33, 2939-2941;
20. c) B. I. Kharisov, S. S. Berdonosov, V. F. Kozlovskii, Vestnik Mask. Univ., Sriya 2: Khimiya 1990, 31, 593-597;
21. d) S. S. Berdonosov, B. I. Kharisov, S. I. Troyanov, I.V. Melikhov, Vestnik Mask. Univ., Sriya 2: Khimiya 1994, 35, 520-524;
22. e) P. S. Ammala, J. D. Cashion, C. M. Kepert, K. S. Murray, B. Moubaraki, L. Spiccia, B. O. West, J. Chem. Soc., Dalton Trans. 2001, 2032-2041;
23. f) E. Hollink, D. W. Stephan, in: Comprehensive Coordination Chemistry II, Vol. 4, (Eds.: J. A. McCleverty, T. J. Meyer), Elsevier, Oxford, 2004, pp. 105-173.
24. W. F. Reynolds, U. R. Priller, Can. J. Chem. 1968, 46, 2787-2791.