Synthesis of α-arylated esters from aryl halides

Chinese Chemical Letters

Volumn 17, Issue 5, 2006, Pages 595-598

  Deng, Wei ^a   Wang, Ye Feng ^a   Liu, Lei ^a   Guo, Qing Xiang ^a  

^a UNIVERSITY OF SCIENCE AND TECHNOLOGY OF CHINA   (China)

Author keywords

arylalkanoic acids; Aryl halide; Cross coupling reaction; CuI; Ethyl acetoacetate

Indexed keywords

EID: 33745863170     PISSN: 10018417     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (26)

1. (a) D. Lednicer, L. A. Mitscher, In The Organic Chemistry of Drug Synthesis; John Wiley: New York, 1980; Vol. 2, p 62.
2. (b) J. Zhang, L. L. Li, H. H. Zou, et al., Chin. J. Chem., 2004, 22, 585.
3. (c) X. H. Sun, H. F. Wang, Y. F. Liu, et al., Chin. J. Org. Chem., 2004, 24, 506.
4. H. C. Hang, E. Drotleff, G. I. Elliott, T. A. Ritsema, J. P. Konopelski, Synthesis, 1999, 398.
5. (a) M. Jorgensen, S. Lee, X. Liu, J. P. Wolkowski, J. F. Hartwig, J. Am. Chem. Soc., 2002, 124, 12557.
6. (b) E. J. Hennessy, S. L. Buchwald, Org. Lett., 2002, 4, 269.
7. (c) S. Tang, Y. Liang, W. J. Lin, J. H. Li, Chin. J. Org. Chem., 2004, 24, 1133.
8. (d) Z. H. Shao, H. B. Zhang, Chin. J. Org. Chem., 2005, 25, 282.
9. For recent examples of Cu-catalyzed cross couplings, see: (a) Y. Fang, C. Li, Chem. Commun., 2005, 3574.
10. (b) L. Xu, D. Zhu, F. Wu, R. Wang, B. Wan, Tetrahedron, 2005, 61, 6553.
11. (c) P. S. Wang, C. K. Liang, M. K. Leung, Tetrahedron, 2005, 61, 2931.
12. (d) T. Hu, C. Li, Org. Lett., 2005, 7, 2035.
13. (e) W. Zhu, D. Ma, J. Org. Chem., 2005, 70, 2696.
14. (i) Q. Cai, W. Zhu, H. Zhang, Y. Zhang, D. Ma, Synthesis, 2005, 496.
15. (j) D. Ma, Y. Zhang, J. Yao, S. Wu, F. Tao, J. Am. Chem. Soc., 1998, 120, 12459.
16. (k) D. Ma, C. Xia, Org. Lett., 2001, 3, 2583.
17. (l) D. Ma, Q. Cai, H. Zhang, Org. Lett., 2003, 5, 2453.
18. (m) D. Ma, Q. Cai, Org. Lett., 2003, 5, 3799.
19. (n) W. Zhu, D. Ma, Chem. Commun., 2004, 888.
20. (o) X. Pan, Q. Cai, D. Ma, Org. Lett., 2004, 6, 1809.
21. (p) D. Ma, F. Liu, Chem. Commun., 2004, 1934.
22. (q) W. Zhu, D. Ma, J. Org. Chem., 2005, 70, 2696.
23. (r) D. Ma, Q. Cai, X. Xie, Synlett, 2005, 1767.
24. (s) For other examples, See: W. Deng, L. Liu, Q. X. Guo, Chin. J. Org. Chem., 2004, 24, 150.
25. X. Xie, G. Cai, D. Ma, Org. Lett., 2005, 7, 4693.
26. 3 (1.73 g, 12.5 mmol), CuI (95 mg, 0.50 mmol), N-methylglycine (1.0 mmol, 20 mol%), aryl iodide (5 mmol), and ethyl acetoacetate (6 mmol) in 10 mL of dioxane was heated at 100 °C under nitrogen atmosphere for 48 h. The resulting suspension was cooled to room temperature and filtered through a 2-3 cm pad of silica gel with 100 mL of EtOAc. The filtrate was concentrated and the residue was purified by chromatography to afford the pure product.