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http://dx.doi.org/10.5012/bkcs.2010.31.6.1621

Catalytic Activity of Supported Rhodium(I) Complex for the Carbonylation of Nitrobenzene: Mechanism for Carbamate Formation  

Kim, Jin-Hyung (Department of Chemistry and Research institute for Basic Sciences, Kyung Hee University)
Kim, Dae-Won (Department of Chemistry and Research institute for Basic Sciences, Kyung Hee University)
Cheong, Min-Serk (Department of Chemistry and Research institute for Basic Sciences, Kyung Hee University)
Kim, Hoon-Sik (Department of Chemistry and Research institute for Basic Sciences, Kyung Hee University)
Mukherjee, Deb Kumar (Department of Chemistry and Research institute for Basic Sciences, Kyung Hee University)
Publication Information
Bulletin of the Korean Chemical Society / v.31, no.6, 2010 , pp. 1621-1627 More about this Journal
Abstract
The investigation of the catalytic activity of supported rhodium(I) complex [Rh(P-S)$(CO)_2$] (P-S; polymer anchored salicylic acid) toward the reductive carbonylation of nitrobenzene in DMF medium has been reported. Use of basic cocatalysts in the reaction medium enhanced the percentage of more useful phenyl carbamates. Spectroscopic studies indicate that the reaction proceeds through a dimer species [Rh(HS)(CO)(C(O)$OCH_3$)(${\mu}-OCH_3)]_2$ and phenyl isocyanate is formed as an intermediate. A plausible reaction mechanism based on the identification of reactive intermediates from the soluble rhodium variety has been proposed for the carbonylation process.
Keywords
Carbonylation; Nitrobenzene; Isocyanate; Carbamates; Polymer-anchored;
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1 Gargulak, J. D.; Gladfelter, W. L. J. Am. Chem. Soc. 1994, 116, 3792.   DOI
2 Johnson, K. A.; Gladfelter, W. L. Organometallics 1990, 9, 2101.   DOI
3 Holy, N. L. J. Org. Chem. 1979, 44, 239.   DOI
4 Thonde, S. S.; Kelkar, A. A.; Bhadbhade, M. M.; Chaudhari, R. V. J. Organomet. Chem. 2005, 690, 1677.   DOI
5 Albano, V. G.; Natile, G.; Panunzi, A. Coord. Chem. Rev. 1994, 133, 67.   DOI
6 Giannoccaro, P.; Tommasi, I.; Aresta, M. J. Organomet. Chem. 1994, 476, 13.   DOI
7 Viege, A. S. Polyhedron 2008, 27, 3177.   DOI
8 Ozawa, F.; Kawasaki, N.; Okamoto, H.; Yamamoto, T.; Yamamoto, A. Organometallics 1987, 6, 1640.   DOI
9 Yamamoto, A.; Ozawa, F.; Osakada, K.; Huang, L.; Son, T. I.; Kawasaki, N.; Doh, M. K. Pure Appl. Chem. 1991, 63, 687.   DOI
10 Gargulak, J. D.; Berry, A. J.; Noirot, M. D.; Gladfelter, W. L. J. Am. Chem. Soc. 1992, 114, 8933.   DOI
11 Trzeciak, A. M.; Ciunik, Z.; Ziolkowski, J. J. Organometallics 2002, 21, 132.   DOI
12 Lee, S. M.; Cho, N. S.; Kim, K. D.; Oh, J. S.; Lee, C. W.; Lee, J. S. J. Mol. Catal. 1992, 73, 43.   DOI
13 Sherlock, S. J.; Boyd, D. C.; Moasser B.; Gladfelter, W. L. Inorg. Chem. 1991, 30, 3626.   DOI
14 Kunin, A. J.; Noirot, M. D.; Gladfelter, W. L. J. Am. Chem. Soc. 1989, 111, 2739.   DOI
15 Islam, S. M.; Mal, D.; Palit, B. K.; Saha, C. R. J. Mol. Catal. A: Chemical 1999, 142, 169.   DOI
16 Basu, A.; Bhaduri, S.; Khwaja, H.; Sharma, R. K. Proceedings of the Indian National Science Academy, Part-A: Physical Sciences 1986, 52, 831.
17 Jayashree, S.; Seayad, A,; Gupte, S. P.; Chaudhari, R. V. Catal. Lett. 1999, 58, 213.   DOI
18 Macho, V.; Kralic, M.; Halmo, F. J. Mol. Catal. A: Chem. 1996, 109, 119.   DOI
19 Orejon, A.; Masdeu-Bulto, A. M.; Salagre, P.; Castillon, S.; Claver, C.; Padilla, A.; Almena, B.; Seranno, F. L. Ind. and Eng. Chem. Res. 2008, 47, 8032.   DOI
20 Gargulak, J. D.; Hoffmann, R. D.; Gladfelter, W. L. J. Mol. Catal. 1991, 68, 289.   DOI
21 Riddick, J. A.; Bunger, W. B. Physical Properties and Methods of Purification-Organic Solvents; Vol. 2, 1986; Weissberger.
22 Mukherjee, D. K.; Saha, C. R. J. Mol. Catal. A: Chemical 2003, 193, 4.
23 Kwaskowska-chec, E.; Ziolkowski, J. J. Trans. Met. Chem. 1983, 8, 103.   DOI
24 Gargulak, J. D.; Noirot, M. D.; Gladfelter, W. L. J. Am. Chem. Soc. 1991, 113, 1054.   DOI
25 Pepper, K. W.; Paisley, H. M.; Young, M. A. J. Chem. Soc. 1953, 4097.   DOI
26 Ragaini, F. Dalton Trans. 2009, 6251.
27 Holy, N. L.; Shalvoy, R. J. Org. Chem. 1980, 45, 1418.   DOI
28 Rode, C. V.; Gupte, S. P.; Chaudhuri, R. V.; Pirozhkov, C. D.; Lapidus, A. L. J. Mol. Catal. 1994, 91, 195.   DOI
29 Cenini, S.; Ragaini, F. Catalytic Reductive Carbonylation of Organic Nitro Compounds; Kluwer Academic publishers: Dordrecht, The Netherlands, 1996.
30 Muzart, J. Tetrahedron 2005, 61(40), 9423.   DOI
31 Ragaini, F.; Cenini, S. J. Mol. Catal. 1996, 109, 1.   DOI
32 Lee, Ch. W.; Cho, N. S.; Kim, K. D.; Oh, J. S.; Lee, S. M.; Lee, J. S J. Mol. Catal. 1993, 81, 17.   DOI
33 Mukherjee, D. K.; Palit, B. K.; Saha, C. R. J. Mol. Catal. 1994, 91, 19.   DOI
34 Gaonkar, S. R.; Sapre, N. Y.; Bhaduri, S.; Kumar, G. S. Macromolecules 1990, 23(14), 3533.   DOI
35 Mukherjee, D. K.; Saha, C. R. J. Catal. 2002, 210, 255.   DOI
36 Tafesh, A. M.; Weiguny, J. Chem. Review 1996, 96, 2035.   DOI
37 Skupinska, J.; Karpinska, M.; Olowek, M. Appl. Catal. A: Gen. 2004, 267, 59.   DOI
38 Stahl, S. Angew. Chem. Int. Ed. 2004, 43, 3400.   DOI
39 Gabriele, B.; Salerno, G.; Costa, M.; Chiusoli, G. P. J. Organomet. Chem. 2003, 68, 219.
40 Kanagasabapathy, S.; Thangaraj, A.; Gupte, S. P.; Chaudhuri, R. V. catalyst Lett. 1994, 25, 361.   DOI