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1769
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3. Typical experimental conditions
Aryl iodide (2.0 mmol), propiolic acid (168.1 mg, 2.4 mmol)
Pd(PPh3)2Cl2 (70.2 mg, 0.1 mmol), 1,4-bis(diphenylphosphino)-
butane (85.3 mg, 0.2 mmol), CuI (38.1 mg, 0.2 mmol), DBU
(730.8 mg, 4.8 mmol) and K2CO3 (331.7 mg, 2.4 mmol) were com-
bined with DMSO (4.0 mL) in a small round-bottomed flask. The
resulting reaction mixture was stirred under aerobic and dark condi-
tions at 30 °C for 6 h and subsequently at 80 °C for 3 h. The solvent
was removed from the reaction mixture under the vacuum. The
crude mixture was dissolved with Et2O (15 mL), washed with brine
(15 mL Â 3), dried over MgSO4, and filtered. The combined solvent
was removed under vacuum, and the resulting crude product was
purified by flash chromatography on silica gel.
8. Cadiot, P.; Chodkiewicz, W. In Chemistry of Acetylnes; Viehe, H. G., Ed.; Marcel
Dekker: New York, 1969; p 597.
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10. (a) Jiang, H.-F.; Tang, J.-Y.; Wang, A. Z.; Deng, G.-H.; Yang, S.-R. Synthesis
2006, 1155; (b) Kamata, K.; Yamaguchi, S.; Kotani, M.; Yamaguchi, K.;
Mizuno, N. Angew. Chem., Int. Ed. 2008, 7, 2407; (c) Li, D.; Yin, K.; Li, J.;
Jia, X. Tetrahedron Lett. 2008, 49, 5918; (d) Adimurthy, S.; Malakar, C. C.;
Beifuss, J. J. Org. Chem. 2009, 74, 5648; (e) Yin, W.; He, C.; Chen, M.;
Zhang, H.; Lei, A. Org. Lett. 2009, 11, 709; (f) Li, L.; Wang, J.; Zhang, G.;
Liu, Q. Tetrahedron Lett. 2009, 50, 4033.
11. Meng, X.; Li, C.; Han, B.; Wang, T.; Chen, B. Tetrahedron 2010, 66, 4029.
12. Hilt, G.; Hengst, C.; Arndt, M. Synthesis 2009, 395.
13. Chen, Z.; Jiang, H.; Wang, A.; Yang, S. J. Org. Chem. 2010, 75, 6700.
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Acknowledgment
15. Nishihara, Y.; Okamoto, M.; Inoue, Y.; Miyazaki, M.; Miyasaka, M.; Takagi, K.
Tetrahedron Lett. 2005, 46, 8661.
This work was supported by National Research Foundation of
Korea Grant funded by the Korean Government (2009-0072357)
and POSCO.
16. Paixao, M. W.; Weber, M.; Braga, A. L.; de Azeredo, J. B.; Deobald, A. M.; Stefani,
H. A. Tetrahedron Lett. 2008, 49, 2366.
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References and notes
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