Abstract
NaBH4 with catalytic amounts of Ni2B as an additive reagent reduced aromatic and aliphatic nitro compounds to the corresponding amines in high to excellent yields. Reduction reactions were carried out in H2O within 3–30 min at room temperature or 75–80 °C. The catalytic activity of Ni2B as an additive reagent was superior to using the in situ precipitated one.
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References
T.C. Nugent, Chiral amine synthesis: methods, developments and applications (Wiley-VCH, 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)
G. Booth, Ullmanns encyclopedia of industrial chemistry (Wiley-VCH, Weinheim, 2000)
S.C. Mitchell, R.H. Waring, Ullmanns encyclopedia of industrial chemistry (Wiley-VCH, Weinheim, 2000)
H.J. Arpe, Industrial organic chemistry, 5th edn. (Wiley-VCH, Weinheim, 2010)
J. Hagen, Industrial catalysis: a practical approach, 2nd edn. (Wiley-VCH, Weinheim, 2006)
A. Ricci, Modern amination methods (Wiley-VCH, Weinheim, 2000)
P.G. Andersson, I.J. Munslow, Modern reduction methods (Wiley-VCH, New York, 2008)
J. Seyden-Penne, Reductions by the alumino and borohydrides in organic synthesis, 2nd edn. (Wiley-VCH, 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)
M. Petrini, R. Ballini, G. Rosini, Synthesis 713 (1987)
A. Nose, T. Kudo, Chem. Pharm. Bull. 29, 1159 (1981)
J.O. Osby, B. Ganem, Tetrahedron Lett. 26, 6413 (1985)
A. Ono, H. Sasaki, F. Yaginuma, Chem. Ind. (Lond) 480 (1983)
S.W. Heinzman, B. Ganem, J. Am. Chem. Soc. 104, 6801 (1982)
T. Satoh, S. Suzuki, Y. Suzuki, Y. Miyaji, Z. Imai, Tetrahedron Lett. 10, 4555 (1969)
S. Kano, Y. Tanaka, E. Sugino, S. Hibino, Synthesis 695 (1980)
J.A. Cowan, Tetrahedron Lett. 27, 1205 (1986)
T. Satoh, S. Suzuki, T. Kikuchi, T. Okada, Chem. Ind. (Lond) 1626 (1970)
H.V. Patel, K.A. Vyas, Org. Prep. Proced. Int. 27, 81 (1995)
B. Zeynizadeh, H. Ghasemi, J. Chem. Res. 542 (2006)
P.D. Ren, S.F. Pan, T.W. Dong, S.H. Wu, Synth. Commun. 25, 3799 (1995)
H.N. Borah, D. Prajapati, J.S. Sandhu, J. Chem. Res. 228 (1994)
P.D. Ren, X.W. Pan, Q.H. Jin, Z.P. Yao, Synth. Commun. 27, 3497 (1997)
K.P. Chary, S.R. Ram, D.S. Iyengar, Synlett 683 (2000)
T. Satoh, N. Mitsuo, M. Nishiki, Y. Inoue, Y. Ooi, Chem. Pharm. Bull. 29, 1443 (1981)
S.E. Yoo, S.H. Lee, Synlett 419 (1990)
S. Gohain, D. Prajapati, J.S. Sandhu, Chem. Lett. 24, 725 (1995)
D. Setamdideh, B. Khezri, M. Mollapour, Oriental J. Org. Chem. 27, 991 (2011)
H.H. Seltzman, B.D. Berrang, Tetrahedron Lett. 34, 3083 (1993)
K. Hanaya, T. Muramatsu, H. Kudo, Y.L. Chow, J. Chem. Soc. Perkin Trans. 1, 2409 (1979)
A. Giannis, K. Sandhoff, Angew. Chem. Int. Ed. Eng. 28, 218 (1989)
A.A. Vlcek, A. Rusina, Proceed. Chem. Soc. 161 (1961)
K. Yanada, H. Yamaguchi, H. Meguri, S. Uchida, J. Chem. Soc. Chem. Commun. 1655 (1986)
P. Ren, T. Dong, S. Wu, Synth. Commun. 27, 1547 (1997)
I. Pogorelic, M. Filipan-Litvic, S. Merkas, G. Ljubic, I. Cepanec, M. Litvic, J. Mol. Catal. A: Chem. 274, 202 (2007)
A. Vizi-Orosz, L. Marko, Transition Met. Chem. 16, 215 (1991)
H.S. Wilkinson, G.J. Tanoury, S.A. Wald, C.H. Senanayake, Tetrahedron Lett. 42, 167 (2001)
J.W. Chen, C.Q. Qin, React. Polym. 16, 287 (1992)
N.M. Yoon, J. Choi, Synlett 135 (1993)
B. Zeynizadeh, K. Zahmatkesh, J. Chin. Chem. Soc. 50, 267 (2003)
B. Zeynizadeh, D. Setamdideh, Synth. Commun. 36, 2699 (2006)
B. Zeynizadeh, D. Setamdideh, J. Chin. Chem. Soc. 52, 1179 (2005)
A.S. Demir, I.M. Akhmedov, O. Sesenoglu, Turk. J. Chem. 23, 123 (1999)
C. Denis, B. Laignel, D. Plusquellec, J.Y. Le Marouille, A. Botrel, Tetrahedron Lett. 37, 53 (1996)
D. Mitchell, C.W. Doecke, L.A. Hay, T.M. Koening, D.D. Wirth, Tetrahedron Lett. 36, 5335 (1995)
R. Sharma, G.H. Voynov, T.V. Ovaska, V.E. Marquez, Synlett 839 (1995)
R. Ballini, G. Bosica, Synthesis 723 (1994)
R. Rai, D.B. Collum, Tetrahedron Lett. 35, 6221 (1994)
K. Hattori, K. Takahashi, N. Sakai, Bull. Chem. Soc. Jpn 65, 2690 (1992)
Y. Hu, M. Uno, A. Harada, S. Takahashi, Bull. Chem. Soc. Jpn 64, 1884 (1991)
Y. Kawajiri, N. Matohashi, J. Chem. Soc. Chem. Commun. 1336 (1989)
R. Fornasier, F. Reniero, P. Scrimin, U. Tonellato, J. Org. Chem. 50, 3209 (1985)
B. Zeynizadeh, M. Kouhkan, Bull. Korean Chem. Soc. 32, 3448 (2011)
M. Kouhkan, B. Zeynizadeh, Bull. Korean Chem. Soc. 32, 3323 (2011)
M. Kouhkan, B. Zeynizadeh, Bull. Korean Chem. Soc. 31, 2961 (2010)
B. Zeynizadeh, D. Setamdideh, F. Faraji, Bull. Korean Chem. Soc. 29, 76 (2008)
H. Firouzabadi, B. Zeynizadeh, Iranian J. Sci. Tech. Trans. 19A, 103 (1995)
C.A. Brown, H.C. Brown, J. Am. Chem. Soc. 85, 1003 (1963)
C.A. Brown, J. Org. Chem. 35, 1900 (1970)
J.F. Knifton, J. Org. Chem. 41, 1200 (1976)
G.S. Samuelsen, V.L. Garik, G.B.L. Smith, J. Am. Chem. Soc. 72, 3872 (1950)
C.F.H. Allen, J. van Allan, Org. Synth. Coll. 3, 63 (1955)
P.M.G. Bavin, Org. Synth. Coll. 5, 30 (1973)
D.J. Collins, A.D. Smith, B.H. Davis, Ind. Eng. Chem. Prod. Res. Dev. 21, 279 (1982)
S.L. Karwa, R.A. Rajadhyaksha, Ind. Eng. Chem. Res. 27, 21 (1988)
F. Zhao, S. Fujita, J. Sun, Y. Ikushima, M. Arai, Catal. Today 98, 523 (2004)
A. Corma, P. Serna, Science 313, 332 (2006)
M.O. Sydnes, M. Isobe, Tetrahedron Lett. 49, 1199 (2008)
P.M. Reis, B. Royo, Tetrahedron Lett. 50, 949 (2009)
J. Wang, Z. Yuan, R. Nie, Z. Hou, X. Zheng, Ind. Eng. Chem. Res. 49, 4664 (2010)
Spectral database for organic compounds (SDBS), http://sdbs.db.aist.go.jp/sdbs/cgi-bin/cre_index.cgi. Accessed Oct 2014
NIST chemistry webbook, http://webbook.nist.gov/chemistry. Accessed Oct 2014
Aldrich catalogue of fine chemicals, 2013–2014
A. Clerici, O. Porta, J. Org. Chem. 50, 76 (1985)
Alfa Easar, http://www.alfa.com, Accessed Oct 2014
R. Imwinkelried, D. Dieter Seebach, Org. Synth. Coll. 8, 495 (1993)
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The authors gratefully appreciated the financial support of this work by the research council of Urmia University.
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Zeynizadeh, B., Zabihzadeh, M. Rapid and green reduction of aromatic/aliphatic nitro compounds to amines with NaBH4 and additive Ni2B in H2O. J IRAN CHEM SOC 12, 1221–1226 (2015). https://doi.org/10.1007/s13738-014-0585-5
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DOI: https://doi.org/10.1007/s13738-014-0585-5