Copper-catalyzed decarboxylative C≡N triple bond formation: Direct synthesis of benzonitriles from phenylacetic acids under O2 atmosphere

Advanced Synthesis and Catalysis

Volumn 356, Issue 8, 2014, Pages 1697-1702

  Feng, Qiang ^a   Song, Qiuling ^a  

^a HUAQIAO UNIVERSITY   (China)

Author keywords

copper; decarboxylation; nitriles; oxygen; phenylacetic acids

Indexed keywords

EID: 84901327043     PISSN: 16154150     EISSN: 16154169     Source Type: Journal    
DOI: 10.1002/adsc.201301001     Document Type: Article

References (39)

1. S. V. Ley, A. W. Thomas, Angew. Chem. 2003, 115, 5558-5607
2. Angew. Chem. Int. Ed. 2003, 42, 5400-5449.
3. F. Monnier, M. Taillefer, Angew. Chem. 2009, 121, 7088-7105
4. Angew. Chem. Int. Ed. 2009, 48, 6954-6971.
5. G. Evano, N. Blanchard, M. Toumi, Chem. Rev. 2008, 108, 3054-3131.
6. D. Zhao, C. Gao, X. Su, Y. He, J. You, Y. Xue, Chem. Commun. 2010, 46, 9049-9051.
7. R. Shang, Y. Fu, Y. Wang, Q. Xu, H.-Z. Yu, L. Liu, Angew. Chem. 2009, 121, 9514-9518
8. Angew. Chem. Int. Ed. 2009, 48, 9350-9354.
9. Z. Rappoport, The Chemistry of the Cyano Group, Interscience Publisher, New York, 1970.
10. R. C. Larock, Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd edn., Wiley-VCH, New York, 1989.
11. A. J. Fatiadi, Preparation and Synthetic Applications of Cyano Compounds, Wiley, New York, 1983.
12. A. Kleemann, B. Kutschner, D. Reichert, Pharmaceutical Substances: Syntheses, Patents, Applications, 4th edn. Georg Thieme Verlag, Stuttgart, 2001.
13. M. B. Smith, J. March, March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure, 6th edn., Wiley, Hoboken, NJ, 2007.
14. T. Oishi, K. Yamaguchi, N. Mizuno, Angew. Chem. 2009, 121, 6404-6406
15. Angew. Chem. Int. Ed. 2009, 48, 6286-6288.
16. K. Ishihara, Y. Furuya, H. Yamamoto, Angew. Chem. 2002, 114, 3109-3112
17. Angew. Chem. Int. Ed. 2002, 41, 2983-2986.
18. K. Yamaguchi, H. Fujiwara, Y. Ogasawara, M. Kotani, N. Mizuno, Angew. Chem. 2007, 119, 3996-3999
19. Angew. Chem. Int. Ed. 2007, 46, 3922-3925.
20. C.-W. Kuo, J.-L. Zhu, J.-D. Wu, C.-M. Chu, C.-F. Yao, K.-S. Shia, Chem. Commun. 2007, 301-303.
21. E. Choi, C. Lee, Y. Na, S. Chang, Org. Lett. 2002, 4, 2369-2371.
22. T. Schareina, A. Zapf, W, Mägerlein, N. Müller, M. Beller, Chem. Eur. J. 2007, 13, 6249-6254.
23. F. G. Buono, R. Chidambaram, R. H. Mueller, R. E. Waltermire, Org. Lett. 2008, 10, 5325-5328.
24. Y. Ren, W. Wang, S. Zhao, X. Tian, J. Wang, W. Yin, L. Cheng, Tetrahedron Lett. 2009, 50, 4595-4597.
25. A. G. Myers, D. Tanaka, M. R. Mannion, J. Am. Chem. Soc. 2002, 124, 11250-11251.
26. D. Tanaka, S. P. Romeril, A. G. Myers, J. Am. Chem. Soc. 2005, 127, 10323-10333.
27. L. J. Gooßen, N. Rodríguez, K. Gooßen, Angew. Chem. 2008, 120, 3144-3164
28. Angew. Chem. Int. Ed. 2008, 47, 3100-3120.
29. L. J. Gooßen, N. Rodríguez, B. Melzer, C. Linder, G. Deng, L. M. Levy, J. Am. Chem. Soc. 2007, 129, 4824-4833.
30. Y. I. Smushkevich, V. Y. Smushkevich, M. I. Usorov, J. Chem. Res. S 1999, 407.
31. C. O. Kangani, B. W. Day, D. E. Kelley, Tetrahedron Lett. 2008, 49, 914-918.
32. K. Mlinaric̈-Majerski, R. Margeta, J. Veljkovic̈, Synlett 2005, 2089-2091.
33. V. J. Huber, R. A. Bartsch, Tetrahedron 1998, 54, 9281-9288.
34. S. Chiba, L. Zhang, G. Y. Ang, B. W.-Q. Hui, Org. Lett. 2010, 12, 2052-2055.
35. W. Zhou, L. Zhang, N. Jiao, Angew. Chem. 2009, 121, 7228-7231
36. Angew. Chem. Int. Ed. 2009, 48, 7094-7097.
37. J. Zanon, A. Klapars, S. L. Buchwald, J. Am. Chem. Soc. 2003, 125, 2890-2891.
38. Z. Shu, Y. Ye, Y. Deng, Y. Zhang, J. Wang, Angew. Chem. 2013, 125, 10769-10770
39. Angew. Chem. Int. Ed. 2013, 52, 10573-10576.