Y. Xu et al.
Table 9. Heck coupling reactions of benzene halide with olefin
have been developed and used in the Suzuki–Miyaura and
Mizoroki–Heck reactions, in which the dendrimer acted as a
stabilizer for preventing the nanoparticles from agglomeration, as
a recycling vehicle, as well as a ligand in catalysis. This novel catalyst
exhibited high activity and stability for the coupling reactions. The
advantages of this procedure are simple operation, short reaction
time, trace amount of catalyst needed, good to excellent yield and
environmental friendliness. Furthermore, it can be easily recovered
and reused up to five times without any apparent loss of activity.
R2
R2
Cat.0.04mol%
R1
X
R1
K3PO4.3H2O
Entry
R1
R2 X Time (h) Yield (%) m.p. (ꢀC) Product [ref.]
1
4-OCH3 Ph
I
1
1
97
84
98
89
25
129–131
127–128
120–121
155–157
120–121
2a 32
2b 33
2c 34
2d 35
2c 34
2a 32
2e 35
2f 32
—
2
4-Cl
H
Ph
Ph
Ph
Ph
I
3
I
1
4
4-NO2
H
Br
Br
Br
Br
Br
Br
Cl
2
5
2
Acknowledgements
6
4-OCH3 Ph
4-CH3 Ph
4-CO2CH3 Ph
2
Trace 129–131
We are grateful to the National Natural Science Foundation of
China (No. 21072077), and the Guangdong Natural Science
Foundation (No. 10151063201000051) for financial support.
7
2
19
78
117–119
157–159
8
2
9
3-NO2
4-NO2
Ph
Ph
2
Trace 109–110
10
11
12
5
61
84
83
155–157
171–172
283–285
2d 35
2g 35
2h 35
4-OCH3 CO2H I
4-NO2 CO2H Br
10
10
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Conclusion
In summary, new silica-supported third-generation dendrimers
capped by DABCO group-stabilized palladium(0) nanoparticles
wileyonlinelibrary.com/journal/aoc
Copyright © 2012 John Wiley & Sons, Ltd.
Appl. Organometal. Chem. 2013, 27, 13–18