Synthesis of 2-alkyl-2-arylcyanoacetates via CuI/sodium picolinate-catalyzed direct arylation of α-substituted cyanoacetates

Tetrahedron Letters

Volumn 54, Issue 29, 2013, Pages 3889-3891

  Xie, Siwei ^a   Qin, Peng ^a   Li, Meng ^a   Zhang, Xiaojing ^a   Jiang, Yongwen ^b   Ma, Dawei ^b  

^a SHENYANG PHARMACEUTICAL UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

Arylation; Catalysis; Cross coupling

Indexed keywords

2 ALKYL 2 ARYLCYANOACETATE; ACETIC ACID DERIVATIVE; COPPER; PICOLINIC ACID; UNCLASSIFIED DRUG;

ARTICLE; ARYLATION; CATALYSIS; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CROSS COUPLING REACTION; ELECTRONICS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 84879023281     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.05.057     Document Type: Article

References (27)

1. W.R.H. Hurtley J. Chem. Soc. 1929 1870
2. C. Giordano, G. Castaldi, and F. Uggeri Angew. Chem., Int. Ed. Engl. 23 1984 413
3. P.J. Harrington, and E. Lodewijk Org. Process Res. Dev. 1 1997 72
4. H. Brunner, and P. Schmidt Eur. J. Org. Chem. 2000 2119
5. For reviews, see: G. Evano, N. Blanchard, and M. Toumi Chem. Rev. 108 2008 3054
6. D. Ma, and Q. Cai Acc. Chem. Res. 41 2008 1450
7. F. Monnier, and M. Taillefer Angew. Chem., Int. Ed. 48 2009 6954
8. D.S. Surry, and S.L. Buchwald Chem. Sci. 2010 13
9. E. Sperotto, G.P.M. Klink, G. Koten, and J.G. Vries J. Chem. Soc., Dalton Trans. 39 2010 10338
10. S.L. Buchwald, and E.J. Hennessy Org. Lett. 4 2002 269
11. X. Xie, G. Cai, and D. Ma Org. Lett. 7 2005 4693
12. Y. Jiang, N. Wu, H. Wu, and M. He Synlett 18 2005 2731
13. S.F. Yip, H.Y. Cheung, Z. Zhou, and F.Y. Kwong Org. Lett. 9 2007 3469
14. H.J. Cristau, P.P. Cellier, J.F. Spindler, and M. Taillefer Chem. Eur. J. 10 2004 5607
15. S. Yan, H. Wu, N. Wu, and Y. Jiang Synthesis 17 2007 2699
16. Y. Chen, X. Xie, and D. Ma J. Org. Chem. 72 2007 9329
17. Y. Chen, Y. Wang, Z. Sun, and D. Ma Org. Lett. 10 2008 625
18. S. Tanimori, H. Ura, and M. Kirihata Eur. J. Org. Chem. 2007 3977
19. C. Chen, and P.G. Dormer J. Org. Chem. 70 2005 6964
20. Y. Fang, and C. Li J. Org. Chem. 71 2006 6427
21. M. Carril, R. SanMartin, I. Tellitu, and D. Esther Org. Lett. 8 2006 1467
22. B. Lu, B. Wang, Y. Zhang, and D. Ma J. Org. Chem. 72 2007 5337
23. B. Wang, B. Lu, Y. Jiang, Y. Zhang, and D. Ma Org. Lett. 10 2008 2761
24. B. Lu, and D. Ma Org. Lett. 8 2006 6115
25. F. Wang, H. Liu, H. Fu, Y. Jiang, and Y. Zhao Org. Lett. 11 2009 2469
26. X. Xie, Y. Chen, and D. Ma J. Am. Chem. Soc. 128 2006 16050
27. S. Pivsa-Art, Y. Fukui, M. Miura, and M. Nomura Bull. Chem. Soc. Jpn. 69 1996 2039