Iron-catalyzed oxidative coupling of alkylamines with arenes, nitroalkanes, and 1,3-dicarbonyl compounds

Chemistry Letters

Volumn 40, Issue 9, 2011, Pages 1041-1043

  Shirakawa, Eiji ^a   Yoneda, Tomoki ^a   Moriya, Kohei ^a   Ota, Kensuke ^a   Uchiyama, Nanase ^a   Nishikawa, Ryo ^a   Hayashi, Tamio ^a  

^a KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 80052579461     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2011.1041     Document Type: Article

References (28)

1. E. Shirakawa, N. Uchiyama, T. Hayashi, J. Org. Chem. 2011, 76, 25.
2. T. Tsuchimoto, Y. Ozawa, R. Negoro, E. Shirakawa, Y. Kawakami, Angew. Chem., Int. Ed. 2004, 43, 4231.
3. M. Ghobrial, K. Harhammer, M. D. Mihovilovic, M. Schnürch, Chem. Commun. 2010, 46, 8836.
4. ̇ abstraction from an alkylamide followed by homolytic aromatic substitution on an electrophilic pyridine derivative with the resulting nucleophilic acylaminomethyl radical is involved. A. Arnone, M. Cecere, R. Galli, F. Minisci, M. Perchinunno, O. Porta, G. P. Gardini, Gazz. Chim. Ital. 1973, 103, 13.
5. For a review: F. Minisci, E. Vismara, F. Fontana, Heterocycles 1989, 28, 489.
6. Under copper catalysis: Z. Li, C.-J. Li, J. Am. Chem. Soc. 2005, 127, 6968.
7. F. Yang, J. Li, J. Xie, Z.-Z. Huang, Org. Lett. 2010, 12, 5214.
8. L. Huang, T. Niu, J. Wu, Y. Zhang, J. Org. Chem. 2011, 76, 1759.
9. Under iron catalysis: M. Ohta, M. P. Quick, J. Yamaguchi, B. Wünsch, K. Itami, Chem.-Asian J. 2009, 4, 1416.
10. P. Liu, C.-Y. Zhou, S. Xiang, C.-M. Che, Chem. Commun. 2010, 46, 2739.
11. See also ref. 2b. Under ruthenium catalysis: M.-Z. Wang, C.-Y. Zhou, M.-K. Wong, C.-M. Che, Chem.-Eur. J. 2010, 16, 5723.
12. Under copper catalysis: Z. Li, C.-J. Li, J. Am. Chem. Soc. 2005, 127, 3672.
13. O. Baslé, C.-J. Li, Green Chem. 2007, 9, 1047.
14. Under ruthenium catalysis: A. Yu, Z. Gu, D. Chen, W. He, P. Tan, J. Xiang, Catal. Commun. 2009, 11, 162.
15. Under platinum catalysis: X.-Z. Shu, Y.-F. Yang, X.-F. Xia, K.-G. Ji, X.-Y. Liu, Y.-M. Liang, Org. Biomol. Chem. 2010, 8, 4077.
16. Under copper catalysis: Z. Li, C.-J. Li, Eur. J. Org. Chem. 2005, 3173.
17. Z. Li, R. Yu, H. Li, Angew. Chem., Int. Ed. 2008, 47, 7497. Iron(0)- catalyzed reaction of 1,3-dicarbonyl compounds with methylamines gives methylene-bridged bis-1,3-dicarbonyl compounds.
18. H. Li, Z. He, X. Guo, W. Li, X. Zhao, Z. Li, Org. Lett. 2009, 11, 4176. Under ruthenium catalysis: ref. 5c. Under platinum catalysis: ref. 5d. Simple ketones with the aid of a catalytic amount of pyrrolidinium benzoate act as nucleophiles: ref. 4b.
19. Iron-catalyzed oxidative coupling of alkylamines with alkynes has been reported: C. M. R. Volla, P. Vogel, Org. Lett. 2009, 11, 1701. See also ref. 4e. Iron-catalyzed oxidative coupling of N,N-dimethylanilines with benzoyl cyanide to give N-cyanomethyl-N-methylanilines also has been reported.
20. S. Murata, K. Teramoto, M. Miura, M. Nomura, Bull. Chem. Soc. Jpn. 1993, 66, 1297.
21. Iron-catalyzed homocoupling of N,N-dimethylanilines involves nucleophilic attack of benzene derivatives: S. Murata, M. Miura, M. Nomura, J. Chem. Soc., Chem. Commun. 1989, 116.
22. S. Murata, M. Miura, M. Nomura, J. Org. Chem. 1989, 54, 4700.
23. For recent reviews on azomethine ylides, see: C. Nájera, J. M. Sansano, Curr. Org. Chem. 2003, 7, 1105.
24. I. Coldham, R. Hufton, Chem. Rev. 2005, 105, 2765.
25. T. M. V. D. Pinhoe Melo, Eur. J. Org. Chem. 2006, 2873.
26. 2 (6b) in DMSO are reported to be 16.4 (ref. and 11.1 (ref. b), respectively. W. N. Olmstead, F. G. Bordwell, J. Org. Chem. 1980, 45, 3299.
27. W. S. Matthews, J. E. Bares, J. E. Bartmess, F. G. Bordwell, F. J. Cornforth, G. E. Drucker, Z. Margolin, R. J. McCallum, G. J. McCollum, N. R. Vanier, J. Am. Chem. Soc. 1975, 97, 7006.
28. Supporting Information is available electronically on the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.