Abstract
The purely aqueous-phase reduction of a wide range of nitro compounds to the corresponding amines has been carried out with NaBH4 in the presence of inexpensive Cu nanoparticles as catalyst. The reactions were taken place in water (80 °C) within 4–15 min to give amines in high to excellent yields.
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References
A.M. Tafesh, J. Weiguny, Chem. Rev. 96, 2035 (1996)
T.C. Nugent, Chiral Amine Synthesis: Methods, Developments and Applications (Wiley, Weinheim, 2010)
T. Farooqui, A.A. Farooqui, Biogenic Amines: Pharmacological, Neurochemical and Molecular Aspects in the CNS (Nova Science, New York, 2010)
S.A. Lawrence, Amines: Synthesis, Properties and Applications (Cambridge University Press, Cambridge, 2004)
P.G. Andersson, I.J. Munslow, Modern Reduction Methods (Wiley, New York, 2008)
J. Seyden-Penne, Reductions by the Alumino and Borohydrides in Organic Synthesis, 2nd edn. (Wiley, New York, 1997)
A.F. Abdel-Magid, Reductions in Organic Synthesis, Vol. 641 (ACS Symposium Series, 1996)
M. Hudlicky, Reductions in Organic Chemistry (Ellis Horwood, Chichester, 1984)
K.-I. Min, J.-S. Choi, Y.-M. Chung, W.-S. Ahn, R. Ryoo, P.K. Lim, Appl. Catal. A Gen. 337, 97 (2008)
M. Takasaki, Y. Motoyama, K. Higashi, S.-H. Yoon, I. Mochida, H. Nagashima, Org. Lett. 10, 1601 (2008)
Y. Motoyamal, Y. Lee, K. Tsuji, S.-H. Yoon, I. Mochida, H. Nagashima, Chem. Cat. Chem. 3, 1578 (2011)
M. Liu, W. Yu, H. Liu, J. Mol. Catal. A Chem. 138, 295 (1999)
M. Boronat, P. Concepción, A. Corma, S. González, F. Illas, P. Serna, J. Am. Chem. Soc. 129, 16230 (2007)
X.-B. Lou, L. He, Y. Qian, Y.-M. Liu, Y. Cao, K.-N. Fan, Adv. Synth. Catal. 353, 281 (2011)
A. Corma, P. Serna, Science 313, 332 (2006)
P. Luo, K. Xu, R. Zhang, L. Huang, J. Wang, W. Xing, J. Huang, Catal. Sci. Technol. 2, 301 (2012)
P. Lignier, R. Bellabarba, R.P. Tooze, Chem. Soc. Rev. 41, 1708 (2012)
A. Nasirian, Int. J. Nano Dim. 2, 159 (2012)
W.M. Haynes, CRC Handbook of Chemistry and Physics, 96th edn. (CRC Press, Boca Raton, 2015)
C.-H. Tu, A.-Q. Wang, M.-Y. Zheng, X.-D. Wang, T. Zhang, Appl. Catal. A Gen. 297, 40 (2006)
R.J. Kalbasi, A.A. Nourbakhsh, M. Zia, J. Inorg. Organomet. Polym. 22, 536 (2012)
B.C. Ranu, R. Dey, T. Chatterjee, S. Ahammed, Chem. Sus. Chem. 5, 22 (2012)
J. Dulle, K. Thirunavukkarasu, M.C. Mittelmeijer-Hazeleger, D.V. Andreeva, N.R. Shiju, G. Rothenberg, Green Chem. 15, 1238 (2013)
S. Ahammed, A. Saha, B.C. Ranu, J. Org. Chem. 76, 7235 (2011)
I. Markova-Deneva, J. Univ. Chem. Tech. Metall. 45, 351 (2010)
T. Petrov, I. Markova-Deneva, O. Chauvet, R. Nikolov, I. Denev, J. Univ. Chem. Tech. Metall. 47, 197 (2012)
P.K. Khanna, T.S. Kale, M. Shaikh, N.K. Rao, C.V.V. Satyanarayana, Mater. Chem. Phys. 110, 21 (2008)
B. Zeynizadeh, M. Zabihzadeh, J. Iran. Chem. Soc. 12, 1221 (2015)
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The financial support of this work was gratefully acknowledged by the Research Council of Urmia University.
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Zeynizadeh, B., Zabihzadeh, M. & Shokri, Z. Cu nanoparticles: a highly efficient non-noble metal catalyst for rapid reduction of nitro compounds to amines with NaBH4 in water. J IRAN CHEM SOC 13, 1487–1492 (2016). https://doi.org/10.1007/s13738-016-0864-4
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DOI: https://doi.org/10.1007/s13738-016-0864-4