A chemoselective and green reduction of nitro arenes to aromatic amines with FeSO4, NaBH4, H3PW12O40 in water at room temperature

Document Type : Research Paper

Authors

Department of Chemistry, Islamic Azad University, Shahreza Branch,86145-311, Shahreza ,Isfahan , Iran.

10.7508/jns.2011.01.004

Abstract

A new efficient and practical method for the room-temperature reduction of aromatic nitro compounds employing FeSO4. 7H2O, NaBH4, H3PW12O40 system in H2O under mild conditions is reported. The method is simple, inexpensive, easily scaled-up and applicable for the large scale preparation of different substituted anilines.

Keywords


[1] A. M. Tafesh, J. Weiguny, J. Chem. Rev. 96 (1996) 2035-2052.
[2] G. H. Coleman, S. M. McClosky, F. A. Suart, Organic Synthesis; Wiley: New York, 1995; Collect. Vol. III, p 668-670.
[3]  A. Saha, B. Ranu, J. Org. Chem. 73 (2008) 6867-6870.
[4] M. Takasaki, Y. Motoyama, K. Higashi, S.-H. Yoon, I. Mochida, H. Nagashima, Org. Lett. 10 (2008) 1601-1604.
[5] A. Corma, P. Serna, Science, 313 (2006) 332-334.
[6]  P. Maity, S. Basu, S. Bhaduri, G. K. Lahiri, Adv. Synth. Catal. 349 (2007) 1955-1962.
[7] S. K. Gosh, M. Mandal, S. Kundu, S. Nath, T. Pal. Appl. Catal. A: Gen. 268 (2004) 61-66.
[8]  Q. Shi, R. Lu, L. Lu, X. Fu, D. Zhao, Adv. Synth. Catal. 349 (2007) 1877-1881.
[9] Y. Zheng, K. Ma, H. Wang, X. Sun, J. Jiang, C. Wang, R. Li, J. Ma, J. Catal. Lett, 124 (2008) 268-276.
[10] F. Cardenas-Lizana, S. Gomez-Quero, M. K. Keane, Cat. Commun, , 9 (2008) 475-481.
[11]  T. Swathi, G. Buvaneswari, Mater. Lett. 62 (2008) 3900-3902.
[12] G. Gao, Y. Tao, J. Jiang, Green Chem. 10 (2008) 439-441.
[13] I. Pogorelic, M. Filipan-Litvic, S. Merkas, G. Ljubic, I. Cepanec, M. Litvic, J. Mol. Catal. A. Chem. 274 (2007) 202-207.
[14] Q. Shi, R. Lu, K. Jin, Z. Zhang, D. Zhao, Green Chem. 8 (2006) 868-870.
[15] P. Li, Z. Wu, J. Yan, M. Wang, Y. Ding, Synthesis (2003) 2001-2004.
[16] J. Ronald. Jr. Rahaim, E. Robert, Jr. Maleczka, Org. Lett. 7 (2005) 5087-5090.
[17] S. U. Sonavane, M. B. Gawande, S. S. Deshpande, A. Venkataraman, R. V.  Jayaram, Catal. Commun. 8 (2007) 1803-1806.
[18] S. Jana, S. K. Ghosh, S. Nath, S. Pande, S. Praharaj, S. Panigrahi, S. Basu, T. Endo, T. Pal, Appl. Catal. A. Gen. 313 (2006) 41-48.
[19]  K. M. Lakshmi, T. Bandyopadhyay, A. Rahman, N. Mahender Reddy, B. M. Choudary J. Mol. Catal A: Chem. 133 (1998) 293-295.
[20] S. Xu, X. Xi, J. Shi, S. Cao, J. Mol. Catal. A: Chem. 160 (2000) 287-292.
[21] Y. Chen, J. Qiu, X. Wang, J. Xiu, J. Catal. 242 (2006) 227-230.
[22] Y. Du, H. Chen, R. Chen, N. Xu, Appl. Catal. A: Gen. 277 (2004) 259-264.
[23] T. Joseph, V. Kumar, A.V. Ramaswamy, S. B.  Halligudi, Catal. Commun. 8 (2007) 629-634.
[24] F. Cardenas-Lizana, S. Gomez-Quero, M. A. Keane, Catal. Cummun. 9 (2008) 475-481.
[25] J-H. Shen, Y-W. Chen, J. Mol. Catal. A:Chem. 273 (2007) 265-276.
[26] Y-S. Keum, Q-X. Li, Chemosphere,  54 (2004) 255-263.
[27] D. He, H. Shi, Y. Wu, B-Q. Xu, Green Chem. 9 (2007) 849-851.
[28] A. S. Kulkarni, R. V. Jayaram, J. Mol. Catal. A:Chem. 223 (2004) 107-110.
[29] S. K. Mohapatra, S. U. Sonavane, R.V. Jayaram, P. Selvam, Org. Lett. 24 (2002) 4297-4300.
[30] M. Lauwiner, P. Res, J. Wissmann, Appl. Catal. A: Gen. 172 (1998) 141-148.
[31] C-R. Zhang, Y-L. Wang, Indian. J. Chem. Sect. B: Org. Chem. Incl. Med. Chem. 45 (2006) 510-511.
[32] M. V. Joshi, D. Mukesh, J. Catal. 168 (1997) 273-277.
[33] D. G. Desai, S. S. Swami, S. B. Hapase, Synthetic. Commun,  29 (1999) 1033-1036.
[34] D. G. Desai, S. S. Swami, S. K. Dabhade, M. G. Ghagare, Synthtic Commun. 31 (2001) 1249-1251.
[35] C. Yu, B. Liu, L. Hu, J. Org. Chem. 66 (2001) 919-924.
[36] H. G. Zheng, J. H. Liang, J. H. Zeng, Y. T. Qian, Mater. Res. Bull. 36 (2001) 947-951.
[37] R. Fazaeli, S. Tangestaninejad, H. Aliyan, M. Moghadam, Appl. Catal. A. Gen.  309 (2006) 44-51.
[38] R. Fazaeli, S. Tangestaninejad, H. Aliyan,  Appl. Catal. A. Gen.  318 (2007) 218-226.
[39] R. Fazaeli, H. Aliyan, Appl. Catal. A. Gen. 331 (2007) 78-83.
[40] R. Fazaeli, H. Aliyan, Appl. Catal. A. Gen. 353 (2009) 74-79.