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H N
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R
H O
2
H O
2
2
R
NH2
R
NH
II
Cu L SO
n
4
OH2
R
R
NH2
2
012, 10, 1618; (v) Huang, B.; Tian, H.; Lin, S.; Xie, M.; Yu, X.; Xu,
R
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NH3
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H O
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R
N
R
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Figure 1. A possible catalytic cycle for the CuSO
4
-catalyzed
oxidation of primary amines with H
O
2 2
3
48, 249; (d) Zhu, B.; Angelici, R. J. Chem. Commun. 2007, 2157.
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In conclusion, a convenient procedure for the oxidation of
amines to the corresponding imines has been developed. The
method is simple to perform, and oxidation of the amines to
imines proceeds under mild conditions, using H O in water at
2 2
room temperature for 1.5 h. Studies are currently underway in
our laboratory to investigate further synthetic applications.
2
Org. Chem. 2012, 4457; (c) Kang, Q.; Zhang, Y. Green Chem. 2012,
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Acknowledgments
(
2
This research was supported by a Grant-in-Aid for Challenging
Exploratory Research (26620149) and Adaptable and Seamless
Technology Transfer Program (JST: A-STEP) from the Ministry
of Education, Culture, Sports, Science and Technology, Japan.
(a) Kodama, S.; Ueta, Y.; Yoshida, J.; Nomoto, A.; Yano, S.; Ueshima,
M.; Ogawa, A. Dalton Trans., 2009, 9708; (b) Kodama, S.; Hashidate,
S.; Nomoto, A.; Yano, S.; Ueshima, M.; Ogawa, A. Chem. Lett. 2011,
40, 495; (c) Kodama, S.; Nomoto, A.; Yano, S.; Ueshima, M.; Ogawa,
A. Inorg. Chem., 2011, 50, 9942.; (d) Marui K.; Higashiura, Y.;
Kodama, S.; Hashidate, S.; Nomoto, A.; Yano, S.; Ueshima, M.;
Ogawa, A. Tetrahedron Lett. 2014, 70, 2431.
Kodama, S.; Yoshida, J.; Nomoto, A.; Ueta, Y.; Yano, S.; Ueshima,
M.; Ogawa, A. Tetrahedron Lett. 2010, 51, 2450
General procedure and supplemental data is shown in supporting
information.
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