J. Mao et al. / Tetrahedron 64 (2008) 1383e1387
1387
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mesh). Analytical thin layer chromatography was performed
using glass plates pre-coated with 200e400 mesh silica gel
impregnated with a fluorescent indicator (254 nm). NMR
spectra were measured in CDCl3 on a Varian Inova-400
NMR spectrometer (400 or 300 MHz) with TMS as an internal
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1
reference. Products were characterized by comparison of H
and 13C NMR data with that in the literatures.
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4.2. General procedure for CeN coupling reactions of
aryl halide and heterocycle
Cu(OAc)2$H2O (0.2 equiv), cesium carbonate (3.0 equiv),
and hippuric acid (0.2 equiv) were added to a screw-capped
test tube. The tube was then evacuated and backfilled with
argon (three cycles). DMF (2 ml), heterocycles (1.2 equiv)
(if liquid), and aryl halide (if liquid) were added by syringe
at room temperature. The tube was again evacuated and back-
filled with argon (three cycles). The mixture was heated to
120e140 ꢀC and stirred for 20e30 h. After cooling to room
temperature, the mixture was diluted with water, and the com-
bined aqueous phases were extracted three times with ethyl ac-
etate. The organic layers were combined, dried over Na2SO4,
and concentrated to yield the crude product, which was further
purified by silica gel chromatography, using petroleum ether
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Acknowledgements
The authors would like to thank the Natural Science
Foundation of Education Committee of Jiangsu Province
(06KJB150099, 05KJB150116), Natural Science Foundation
of Jiangsu Province (BK2006048), Natural Science Founda-
tion of China (20472062, 20672079), China Postdoctoral Sci-
ence Foundation, and Key Laboratory of Organic Synthesis of
Jiangsu Province for financial support.
13. Jiang, D.; Fu, H.; Jiang, Y.; Zhao, Y. J. Org. Chem. 2007, 72, 672e674.
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62, 4435e4443.
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Supplementary data
Supplementary data associated with this article can be
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