Selective Reduction of Nitroarenes with Molybdenum Disulfide
Lei Huang
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing, Jiangsu 210009, China
Search for more papers by this authorPingfei Luo
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing, Jiangsu 210009, China
Search for more papers by this authorMan Xiong
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing, Jiangsu 210009, China
Search for more papers by this authorRizhi Chen
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing, Jiangsu 210009, China
Search for more papers by this authorYong Wang
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing, Jiangsu 210009, China
Search for more papers by this authorWeihong Xing
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing, Jiangsu 210009, China
Search for more papers by this authorCorresponding Author
Jun Huang
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing, Jiangsu 210009, China
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing, Jiangsu 210009, China, Tel.: 0086-025-83172276; Fax: 0086-025-83172261Search for more papers by this authorLei Huang
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing, Jiangsu 210009, China
Search for more papers by this authorPingfei Luo
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing, Jiangsu 210009, China
Search for more papers by this authorMan Xiong
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing, Jiangsu 210009, China
Search for more papers by this authorRizhi Chen
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing, Jiangsu 210009, China
Search for more papers by this authorYong Wang
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing, Jiangsu 210009, China
Search for more papers by this authorWeihong Xing
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing, Jiangsu 210009, China
Search for more papers by this authorCorresponding Author
Jun Huang
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing, Jiangsu 210009, China
State Key Laboratory of Materials-Oriented Chemical Engineering, College of Chemistry and Chemical Engineering, Nanjing University of Technology, Nanjing, Jiangsu 210009, China, Tel.: 0086-025-83172276; Fax: 0086-025-83172261Search for more papers by this authorAbstract
Commercial MoS2 was found to be a highly selective catalyst for the reduction of nitrobenzenes to the corresponding anilines with hydrazine under mild conditions. MoS2 is not only much cheaper, but also more selective than noble metal catalysts for the reduction of functional nitrobenzenes to the corresponding anilines. Nitrobenzenes with halides (F, Cl, Br and I) were reduced selectively, and the corresponding anilines were obtained in excellent yields, and no dehalogenation was detected. Functional groups such as NH2, OH, alkene groups were tolerated during the reduction of the nitro compounds. The reduction of p-chloronitrobenzene was studied over MoS2 and Pd/C respectively with hydrazine. The yield of p-chloroaniline was much higher with MoS2 than that with Pd/C at full conversion.
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REFERENCES
- 1 Booth, G., Ullmanns Encyclopedia of Industrial Chemistry, Wiley-VCH Verlag, Weinheim, Germany, 2002.
- 2 Sheldon, R. A.; van Bekkum, H., Fine Chemicals through Heterogeneous Catalysis, Wiley-VCH, Weinheim, 2001.
- 3a Wang, F.; Liu, J.; Xu, X.. Chem. Commun., 2008, 17, 2040.
- 3b Li, M.; Hu, L.; Cao, X.; Hong, H.; Lu, J.; Gu, H.. Chem. Eur. J., 2011, 17, 2763.
- 3c Pandarus, V.; Ciriminna, R.; Beland, F.; Pagliaro, M.. Adv. Synth. Catal., 2011, 353, 1306.
- 3d Nie, R.; Wang, J.; Wang, L.; Qin, Y.; Chen, P.; Hou, Z.. Carbon, 2012, 50, 586.
- 3e Motoyama, Y.; Kamo, K.; Nagashima, H.. Org. Lett., 2009, 11, 1345.
- 3f Lian, C.; Liu, H.; Xiao, C.; Yang, W.; Zhang, K.; Liu, Y.; Wang, Y.. Chem. Commun., 2012, 48, 3124.
- 3g Liu, H.; Lu, G.. Chinese. J. Inorg. Chem., 2011, 27, 2045.
- 3h Han, X.; Li, J.; Zhou, R.. Chin. Chem. Lett., 2009, 20, 96.
- 4a Pandarus, V.; Ciriminna, R.; Beland, F.; Pagliaro, M.. Catal. Sci. Technol., 2011, 1, 1616.
- 4b Li, J.; Shi, X.; Bi, Y.; Wei, J.; Chen, Z.. ACS Catal., 2011, 1, 657.
- 4c Zhang, R.; Liu, J.; Li, F.; Wang, S.; Xia, C.; Sun, W.. Chin. J. Chem., 2011, 29, 525.
- 4d Yan, R.; Xu, J.; Zhang, Y.; Wang, D.; Zhang, M.; Zhan, W.. Chem. Eng. J., 2012, 200−202, 559.
- 4e Chatterjee, M.; Ishizaka, T.; Suzuki, T.; Suzuki, A.; Kawanami, H.. Green Chem., 2012, 14, 3415.
- 4f Harraza, F. A.; El-Houta, S. E.; Killab, H. M.; Ibrahima, I. A.. J. Catal., 2012, 286, 184.
- 5a Zhao, S.; Liang, H.; Zhou, Y.. Catal. Commun., 2007, 8, 1305.
- 5b Chary, K. V. R.; Srikanth, C. S.. Catal. Lett., 2009, 128, 164.
- 5c Cui, X.; Shi, F.; Deng, Y.. ChemCatChem, 2012, 4, 333.
- 5d Antonetti, C.; Oubenali, M.; Galletti, A. M. R.; Serpb, P.; Vannucci, G.. Appl. Catal. A: Gen., 2012, 421−422, 99.
- 6a Corma, A.; Serna, P.. Science, 2006, 313, 332.
- 6b Corma, A.; Concepcion, P.; Serna, P.. Angew. Chem., Int. Ed., 2007, 46, 7266.
- 6c Makosch, M.; Sa, J.; Kartusch, C.; Richner, G.; van Bokhoven, J. A.; Hungerbuhler, K.. ChemCatChem, 2012, 4, 59.
- 6d Boronat, M.; Concepcion, P.; Corma, A.; Gonzalez, S.; Illas, F.; Serna, P., J. Am. Chem. Soc., 2007, 129, 16230.
- 7a Li, H.; Xu, Y.; Yang, H.; Zhang, F.; Li, H.. J. Mol. Catal. A: Chem., 2009, 307, 105.
- 7b Lin, M.; Zhao, B.; Chen, Y.. Ind. Eng. Chem. Res., 2009, 48, 7037.
- 7c Li, H.; Zhao, Q.; Li, H.. J. Mol. Catal. A: Chem., 2008, 285, 29.
- 7d Mohan, V.; Pramod, C. V.; Suresh, M.; Hari Prasad Reddy, K.; David Raju, B.; Rama Rao, K. S.. Catal. Commun., 2012, 18, 89.
- 7e Lin, W.; Cheng, H.; Ming, J.; Yu, Y.; Zhao, F.. J. Catal., 2012, 291, 149.
- 7f Raj, K. J. A.; Prakash, M. G.; Mahalakshmy, R.; Elangovan, T.; Viswanathan, B.. Chin. J. Catal., 2012, 33, 1299.
- 7g Bai, Y.; Zhu, X.; Zhang, L.; Xu, N.. Chin. J. Catal., 2013, 34, 263.
- 8a Cardenas-Lizana, F.; Gomez-Quero, S.; Perret, N.; Keane, M. A.. Catal. Sci. Technol., 2011, 1, 652.
- 8b Cardenas-Lizana, F.; de Pedro, Z. M.; Gomez-Quero, S.; Keane, M. A.. J. Mol. Catal. A, 2010, 326, 48.
- 9a Wienhofer, G.; Sorribes, I.; Boddien, A.; Westerhaus, F.; Junge, K.; Junge, H.; Llusar, R.; Beller, M.. J. Am. Chem. Soc., 2011, 133, 12875.
- 9b Lou, X.; He, L.; Qian, Y.; Liu, Y.; Cao, Y.; Fan, K.. Adv. Synth. Catal., 2011, 353, 281.
- 9c Junge, K.; Wendt, B.; Shaikh, N.; Beller, M.. Chem. Commun., 2010, 46, 1769.
- 9d Jagadeesh, R. V.; Wienhofer, G.; Westerhaus, F. A.; Surkus, A.; Pohl, M.; Junge, H.; Junge, K.; Beller, M.. Chem. Commun., 2011, 47, 10972.
- 9e Gowda, S.; Gowda, D. C.. Indian J. Chem., 2003, 42B, 180.
- 9f Hirashima, T.; Manabe, O.. Chem. Lett., 1975, 259.
- 9g Zhou, H.; Shi, L.; Sun, Q.. Chin. J. Catal., 2012, 33, 1463.
- 9h Jiang, H.; Dong, Y.. Chin. J. Chem., 2008, 26, 1407.
- 10a Xu, K.; Zhang, Y.; Chen, X.; Huang, L.; Zhang, R.; Huang, J.. Adv. Synth. Catal., 2011, 353, 1260.
- 10b Luo, P.; Xu, K.; Zhang, R.; Huang, L.; Wang, J.; Xing, W.; Huang, J.. Catal. Sci. Technol., 2012, 2, 301.
- 10c Huang, L.; Luo, P.; Pei, W.; Liu, X.; Wang, Y.; Wang, J.; Xing, W.; Huang, J.. Adv. Synth. Catal., 2012, 354, 2689.
- 11a Okuhara, T.; Tanaka, K.. J. Chem. Soc., Faraday Trans. 1, 1979, 75, 1403.
- 11b Wambeke, A.; Jalowiecki, L.; Kasztelan, S.; Grimblot, J.; Bonnelle, J. P.. J. Catal., 1988, 109, 320.
- 12a Huang, M.; Cho, K.. J. Phys. Chem. C, 2009, 113, 5238.
- 12b Surisetty, V. R.; Tavasoli, A.; Dalai, A. K.. Appl. Catal. A: Gen., 2009, 365, 243.
- 13a Sampieri, A.; Pronier, S.; Blanchard, J.; Breysse, M.; Brunet, S.; Fajerwerg, K.; Louis, C.; Perot, G.. Catal. Today, 2005, 107−108, 537.
- 13b Tye, C. T.; Smith, K. J.. Catal. Today, 2006, 116, 461.
- 13c Yoosuk, B.; Kim, J. H.; Song, C.; Ngamcharussrivichai, C.; Prasassarakich, P.. Catal. Today, 2008, 130, 14.
- 13d Ho, T. C.; McConnachie, J. M.. J. Catal., 2011, 277, 117.
- 14 Sun, D.; Lin, B.; Xu, B.; He, L.; Ding, C.; Chen, Y.. J. Porous Mater., 2008, 15, 245.
- 15 Ruiz, P. E.; Frederick, B. G.; De Sisto, W. J.; Austin, R. N.; Radovic, L. R.; Leiva, K.; Garcia, R.; Escalona, N.; Wheeler, M. C.. Catal. Commun., 2012, 27, 44.
- 16 Sorribes, I.; Wienhofer, G.; Vicent, C.; Junge, K.; Llusar, R.; Beller, M.. Angew. Chem., Int. Ed., 2012, 51, 7794.
- 17 Schwarz, G.; Mendel, R. R.; Ribbe, M. W.. Nature, 2009, 460, 839.
- 18
Bullock, R. M., Catalysis without Precious Metals, Wiley-VCH, Weinheim, 2010.
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