Reduction, imine, palladium(II) acetate, triethylsilane, amines
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Finally, we studied the performance of the Et3SiH/EtOH/Pd
(OAc)2 system for the reduction of alkyl imines. The reaction
of N-cyclohexylideneaniline, N-benzylidenepropan-1-amine and
N-cyclohexylidenepropan-1-amine with 1.5 equiv. of Et3SiH in
the presence of 5 mol% Pd(OAc)2 gave N-cyclohexylaniline,[19]
N-benzylpropan-1-amine[24] and N-(n-propyl)cyclohexanamine[25]
in 90%, 75% and 79% yield respectively after 30 min (Table 1,
entries 10–12). The results highlight the high efficiency of Pd
(OAc)2 for the reduction of a wide range of imines.
Conclusion
We have developed an efficient and simple method for the
synthesis of various amine derivatives by the reduction of aromatic,
heteroaromatic and aliphatic imine compounds using a Et3SiH/Pd
(OAc)2 system in ethanol. The utility of this methodology will make
this simple technique an attractive addition to the range of proce-
dures already known for this general transformation.
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General procedure for the reduction of imine
compounds
To a solution of an imine compound (0.2 g, 1 equiv.) and triethylsilane
(1.5 equiv.) in 5 ml ethanol was added a catalytic amount of
palladium(II) acetate under an argon atmosphere. The resulting
mixture was kept under stirring for the time indicated in Table 1
prior to gas chromatographic–mass spectrometric analysis. The
mixture was filtered and evaporated under reduced pressure.
Pure products were isolated by column chromatography using
hexane–ethyl acetate (10/1) as eluent. The products were
characterized by 1H NMR and mass spectrometry.
[10] M. Mirza-Aghayan, R. Boukherroub, M. Bolourtchian, J. Organomet.
Chem. 2005, 690, 2372.
[11] M. Mirza-Aghayan, R. Boukherroub, M. Bolourtchian, M. Rahimifard,
J. Organomet. Chem. 2007, 692, 5113.
[12] M. Mirza-Aghayan, R. Boukherroub, M. Rahimifard, J. Organomet.
Chem. 2008, 693, 3567.
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[14] M. Mirza-Aghayan, R. Boukherroub, M. Rahimifard, R. Zadmard,
Acknowledgment
J. Iran. Chem. Soc. 2011, 8, 570.
[15] M. Mirza-Aghayan, R. Boukherroub, M. Rahimifard, M. Bolourtchian,
Appl. Organomet. Chem. 2010, 24, 477.
[16] A. Martínez-Asencio, M. Yus, D. J. Ramón, Synthesis 2011, 3730.
[17] A. Martínez-Asencio, D. J. Ramón, M. Yus, Tetrahedron 2011, 67, 3140.
[18] J. P. Wolfe, H. Tomori, J. P. Sadighi, J. Yin, S. L. Buchwald, J. Org. Chem.
2000, 65, 1158.
The authors would like to thank the Iran National Science
Foundation (INSF) for financial support.
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Appl. Organometal. Chem. (2013)
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