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http://dx.doi.org/10.5012/bkcs.2006.27.8.1171

Coupling Reaction of CO2 with Epoxides by Binary Catalytic System of Lewis Acids and Onium Salts  

Bok, Taekki (Department of Molecular Science and Technology, Ajou University)
Noh, Eun Kyung (Department of Molecular Science and Technology, Ajou University)
Lee, Bun Yeoul (Department of Molecular Science and Technology, Ajou University)
Publication Information
Abstract
Various off-the-shelf Lewis acids in conjunction with various onium salts are screened for coupling reaction of $CO_2$ with epoxides. Among the tested ones, $VCl_3/n-Bu_4NOAc$, $VCl_3/(n-Bu_4NCl$ or PPNCl), $FeCl_3/ n-Bu_4NOAc$, and $FeCl_3/ n-Bu_4NOAc$are proved to be highly active. Propylene oxide, epichlorohydrin, styrene oxide, and cyclohexene oxide can be converted over 90% yields to the corresponding cyclic carbonates without the use of organic solvents under mild conditions by 0.1-1.0 mol% catalyst charge.
Keywords
Cyclic carbonatel; Carbon dioxide; Epoxide; Coupling reaction;
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1 Kim, Y. J.; Varma, R. S. J. Org. Chem. 2005, 70, 7882   DOI   ScienceOn
2 Mori, K.; Mitani, Y.; Hara, T.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 2005, 3331
3 Lu, X.-B.; Shi, L.; Wang, Y.-M.; Zhang, R.; Zhang, Y.-J.; Peng, X.-J.; Zhang, Z.-C.; Li, B. J. Am. Chem. Soc. 2006, 128, 1664   DOI   ScienceOn
4 Lu, X.-B.; Wang, Y. Angew. Chem., Int. Ed. 2004, 43, 3574   DOI   ScienceOn
5 Peng, J. J.; Deng, Y. Q. New J. Chem. 2001, 25, 639   DOI
6 Yang, H.; Deng, Y.; Shi, F. Chem. Commun. 2002, 274
7 Kawanami, H.; Sakaki, A.; Matsui, K.; Ikushima, Y. Chem. Commun. 2003, 896
8 Calo, W.; Nacci, A.; Monopoli, A.; Fanizzi, A. Org. Lett. 2002, 4, 2561   DOI   ScienceOn
9 Shen, Y. M.; Duah, W. L.; Shi, M. Adv. Synth. Catal. 2003, 345, 337   DOI   ScienceOn
10 Kawanami, H.; Ikushima, Y. Chem. Commun. 2000, 2089
11 Jiang, J.-L.; Gao, F.; Hua, R.; Qiu, X. J. Org. Chem. 2005, 70, 381   DOI   ScienceOn
12 Yasuda, H.; He, L. N.; Sakakura, T. J. Catal. 2002, 209, 547   DOI   ScienceOn
13 Kim, H. S.; Kim, J. J.; Lee, B. G.; Jung, O. S.; Jang, H. G.; Kang, S. O. Angew. Chem., Int. Ed. 2000, 39, 4096   DOI   ScienceOn
14 Kim, H. S.; Kim, J. J.; Lee, S. D.; Lah, M. S.; Moon, D.; Jang, H. G. Chem. Eur. J. 2003, 9, 678   DOI   ScienceOn
15 Behr, A. Angew. Chem., Int. Ed. Engl. 1988, 27, 661   DOI   ScienceOn
16 Santamaria, D.; Cano, J.; Royo, P.; Mosquera, M. E. G.; Cuenca, T.; Frutos, L. M.; Castano, O. Angew. Chem., Int. Ed. 2005, 44, 5828   DOI   ScienceOn
17 Kong, L.-Y.; Zhang, Z.-H.; Zhu, H.-F.; Kawaguchi, H.; Okamura, T.; Doi, M.; Chu, Q.; Sun, W.-Y.; Ueyama, N. Angew. Chem., Int. Ed. 2005, 44, 4352   DOI   ScienceOn
18 Hill, M.; Wendt, O. F. Organometallics 2005, 24, 5772   DOI   ScienceOn
19 Coates, G. W.; Moore, D. R. Angew. Chem., Int. Ed. 2004, 43, 6618   DOI   ScienceOn
20 Darensbourg, D. J.; Mackiewicz, R. M. J. Am. Chem. Soc. 2005, 127, 14026   DOI   ScienceOn
21 Cohen, C. T.; Chu, T.; Coates, G. W. J. Am. Chem. Soc. 2005, 127, 10869   DOI   ScienceOn
22 Lee, B. Y.; Kwon, H. Y.; Lee, S. Y.; Na, S. J.; Han, S.-i.; Yun, H.; Lee, H.; Park, Y.-W. J. Am. Chem. Soc. 2005, 127, 3031   DOI   ScienceOn
23 Paddock, R. L.; Nguyen, S. T. Macromolecules 2005, 38, 6251   DOI   ScienceOn
24 Sun, J.; Fujita, S.-i.; Zhao, F.; Arai, M. Green Chem. 2004, 6, 613   DOI   ScienceOn
25 Li, F.; Xiao, L.; Xia, C.; Hu, B. Tetrahedron Lett. 2004, 45, 8307   DOI   ScienceOn
26 Xiao, Y.; Wang, Z.; Ding, K. Macromolecules 2006, 39, 128   DOI   ScienceOn
27 Shaikh, A.-A.; Sivaram, S. Chem. Rev. 1996, 96, 951   DOI   ScienceOn
28 Shen, Y.-M.; Duan, W.-L.; Shi, M. J. Org. Chem. 2003, 68, 1559   DOI   ScienceOn
29 Castro-Rodriguez, I.; Nakai, H.; Zakharov, L. N.; Rheingold, A. L.; Meyer, K. Science 2004, 305, 1757   DOI   ScienceOn
30 Takeda, N.; Inoue, S. Bull. Chem. Soc. Jpn. 1978, 51, 3564   DOI
31 Millward, A. R.; Yaghi, O. M. J. Am. Chem. Soc. 2005, 127, 17998   DOI   ScienceOn
32 Ji, D.; Lu, X.; He, R. Appl. Catal. A: Gen. 2000, 203, 329   DOI   ScienceOn
33 Darensbourg, D. J.; Holtcamp, M. W. Coord. Chem. Rev. 1996, 153, 155   DOI   ScienceOn
34 Inoue, S.; Koinuma, H.; Tsuruta, T. Makromol. Chem. 1969, 130, 210   DOI
35 Mori, K.; Mitani, Y.; Hara, T.; Mizugaki, T.; Ebitani, K.; Kaneda, K. Chem. Commun. 2005, 3331
36 Aida, T.; Inoue, S. J. Am. Chem. Soc. 1983, 105, 1304   DOI   ScienceOn
37 Paddock, R. L.; Hiyama, Y.; Mckay, J. M.; Nguyen, S. T. Tetrahedron Lett. 2004, 45, 2023   DOI   ScienceOn
38 Kisch, H.; Millini, R.; Wang, I. Chem. Ber. 1986, 119, 1090   DOI
39 Barbarini, A.; Maggi, R.; Mazzacani, A.; Mori, G.; Sartori, G.; Sartrio, R. Tetrahedron Lett. 2003, 44, 2931   DOI   ScienceOn
40 Sit, W. N.; Ng, S. M.; Kwong, K. Y.; Lau, C. P. J. Org. Chem. 2005, 70, 8583   DOI   ScienceOn
41 Chang, C. C.; Liao, M.-C.; Chang, T.-H.; Peng, S.-M.; Lee, G.-H. Angew. Chem., Int. Ed. 2005, 44, 7418   DOI   ScienceOn
42 Darensbourg, D. J.; Phelps, A. L.; Gall, N. L.; Jia, L. Acc. Chem. Res. 2004, 37, 836   DOI   ScienceOn
43 Paddock, R. L.; Nguyen, S. T. J. Am. Chem. Soc. 2001, 123, 11498   DOI   ScienceOn
44 Marks, T. J. et al. Chem. Rev. 2001, 101, 953   DOI   ScienceOn