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Table 4 Comparisons of Ps-TiCl4 and Ps-FeCl3 with various
catalysts in tetrahydropyranylationa
Entry Catalyst
Mol/%
15
Time/min Yield/%
1
2
3
4
5
6
7
8
Ps-TiCl4
80
100
42
95
Ps-FeCl3
15
81
Ps-AlCl3
15
97[24a]
97[24c]
96[10]
91[14]
72[12]
59[17]
Ps-tin porphyrin
Carbon catalyst
CuSO4•5H2O
PdCl2(CH3CN)2
polyaniline salt
1
10b
4
120
40
20
10
60
17
480
a Substrate: benzyl alcohol and DHP. b Mass percentage.
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Experimental results suggested that tetrahydropyranyla-
tion occurred in the solid matrix of Ps-TiCl4 and
Ps-FeCl3 rather than catalyzed by free TiCl4 and FeCl3
released from the support. Mild reaction conditions,
good to excellent yields, easy preparation and low cost
were the obvious advantages of the present approach,
and these two supported catalysts can be recovered and
reused for five times with good activity.
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Acknowledgement
The authors would like to thank Dr. Linshen Chen
for TGA, Dr. Jingke Zhu for infrared spectra and Dr.
Zhengbao Wang for pyridine-adsorbed IR. This work
was supported by the NSFC (No. 21176213), and Zhe-
jiang Key Innovation Team of Green Pharmaceutical
Technology (No. 2010R50043).
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Chin. J. Chem. 2012, 30, 2567—2572