Albadi & Mansournezhad
COMMUNICATION
Table 2 Amination of aryl halides catalyzed by CuO-CeO2
nanocomposite in watera
types of functional group transformations.
Acknowledgement
Entry
1
Aryl halide
C6H5I
Product
C6H5NH2
t/h Yieldb/%
4
7
92
90
90
89
90
90
89
92
90
92
90
89
88
88
90
90
We are thankful to the Behbahn Khatam Alanbia
University of Technology for the support of this work.
2
4-MeOC6H4I
3,4,5-(OMe)3C6H2I
4-OMeC6H4NH2
3,4,5-(OMe)3C6H2NH2
3
9
References
4
2,4-Me2-6-NO2C6H2I 2,4-Me2-6-NO2C6H2NH2
3,5-Me2-4-NO2C6H2I 3,5-Me2-4-NO2C6H2NH2
3
5
2
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6
4-MeC6H4I
4-N(Me)2-C6H4I
4-NO2C6H4I
4-ClC6H4I
4-MeC6H4NH2
4-N(Me)2-C6H4NH2
4-NO2C6H4NH2
4-ClC6H4NH2
4.5
6
7
8
1
9
2.5
1
10
11
12
13
14
15
16
4-CF3C6H4I
3-CF3C6H4I
C6H5Br
4-CF3C6H4NH2
3-CF3C6H4NH2
C6H5NH2
1.5
4.5
8
[7] Desmarets, C.; Schneider, R.; Fort, Y. J. Org. Chem. 2002, 67, 3029.
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4-OMeC6H4Br
4-MeC6H4Br
3-MeC6H4Br
4-NO2C6H4Br
4-OMeC6H4NH2
4-MeC6H4NH2
3-MeC6H4NH2
4-NO2C6H4NH2
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5
3.5
2
a Reaction conditions: aryl halide (1 mmol), NH4OH (2 mmol),
Cs2CO3 (1 mmol), catalyst amount (0.07 g) in water at reflux
conditions. b Isolated pure products.
Table 3 Recyclability study of CuO-CeO2 nanocomposite
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Run
t/h
Yielda/%
1
4
4.5
5
92
90
90
87
75
2
3
4
6
5
9
a Isolated yield.
Table 4 Scale-up experimenta
Entry Aryl halide/mmol Amount of catalyst/g
t/h Yieldb/%
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1
2
3
1
2
3
0.07
0.14
0.21
4
4
4
92
92
92
a Reaction conditions: iodobenzene (1, 2 and 3 mmol), NH4OH (2,
4 and 6 mmol), Cs2CO3 (1, 2 and 3 mmol), in water at reflux
conditions. b Isolated pure products.
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Conclusions
In conclusion, a simple and efficient procedure for
the amination of aryl halides with aqueous ammonia in
the presence of CuO-CeO2 nanocomposite in water was
developed. The introduced catalyst can promote the
yields and reaction times over 5 runs and the desired
product was obtained in high yields after 1-5 runs.
Moreover, ease of work-up and clean procedure, will
make the present method a useful and important addi-
tion to the available methods. We are exploring further
applications of CuO-CeO2 nanocomposite for other
(Zhao, C.)
398
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Chin. J. Chem. 2014, 32, 396—398