Copper-catalyzed direct oxidative C-H amination of benzoxazoles with formamides or secondary amines under mild conditions

Journal of Organic Chemistry

Volumn 76, Issue 13, 2011, Pages 5444-5449

  Li, Yaming ^a   Xie, Yusheng ^a   Zhang, Rong ^a   Jin, Kun ^a   Wang, Xiuna ^a   Duan, Chunying ^a  

^a DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

FORMAMIDES; PRACTICAL METHOD; SECONDARY AMINES;

CATALYSIS;

AMINES;

AMINE; BENZOXAZOLE DERIVATIVE; COPPER; FORMAMIDE DERIVATIVE; OXIDIZING AGENT; OXYGEN;

AIR; AMINATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; OXIDATION; SUBSTITUTION REACTION; SYNTHESIS;

AIR; AMINATION; AMINES; BENZOXAZOLES; CATALYSIS; COPPER; FORMAMIDES; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; OXIDATION-REDUCTION; OXYGEN; STEREOISOMERISM;

EID: 79959629593     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo200447x     Document Type: Article

References (38)

1. Hili, R.; Yudin, A. K. Nat. Chem. Biol. 2006, 2, 284
2. Amino Group Chemistry, From Synthesis to the Life Sciences; Ricci, A., Eds.; Wiley-VCH: Weinheim, 2007.
3. Seregin, I. V.; Gevorgan, V. Chem. Soc. Rev. 2007, 36, 1173 and references therein
4. Armstrong, A.; Collins, J. C. Angew. Chem., Int. Ed. 2010, 49, 2282
5. Muci, A. R.; Buchwald, S. L. Top. Curr. Chem. 2002, 219, 131
6. Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338
7. Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534
8. Selected examples: Antilla, J. C.; Buchwald, S. L. Org. Lett. 2001, 3, 2077
9. Kwong, F. Y.; Buchwald, S. L. Org. Lett. 2003, 5, 793
10. Ley, S. V.; Thomas, A. W. Angew. Chem., Int. Ed. 2003, 42, 5400
11. Ma, D. W.; Cai, Q.; Zhang, H. Org. Lett. 2003, 5, 2453
12. Shafir, A.; Buchwald, S. L. J. Am. Chem. Soc. 2006, 128, 8472
13. Evano, G.; Blanchard, N.; Toumi, M. Chem. Rev. 2008, 108, 3054
14. Rao, H.; Fu, H.; Jiang, Y.; Zhao, Y. Angew. Chem., Int. Ed. 2009, 48, 1114
15. Ma, D.; Xia, C. Org. Lett. 2001, 3, 2583
16. Selected examples: Ayker, G. Angew. Chem., Int. Ed. 1999, 38, 1698
17. Thalji, R. K.; Ahrendt, K. A.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2001, 123, 9692
18. Ritleng, V.; Sirlin, C.; Pfeffer, G. Chem. Rev. 2002, 102, 1731
19. Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790
20. Thansandote, P.; Lautens, M. Chem.-Eur. J. 2009, 15, 5874
21. Bouffard, J.; Itami, K. Top. Curr. Chem. 2010, 292, 231
22. Beck, E. M.; Gaunt, M. J. Top. Curr. Chem. 2010, 292, 85
23. For reviews on direct C-H amination reactions, see: Collet, F.; Dodd, R. H.; Dauban, P. Chem. Commun. 2009, 5061
24. Zalatan, D. N.; Bois, J. D. Top. Curr. Chem. 2010, 292, 347
25. Armstrong, A.; Collins, J. C. Angew. Chem., Int. Ed. 2010, 49, 2282
26. Monguchi, D.; Fujiwara, T.; Furukawa, H.; Mori, A. Org. Lett. 2009, 11, 1607
27. Wang, Q.; Schreiber, S. L. Org. Lett. 2009, 11, 5178
28. Kawano, T.; Hirano, K.; Satoh, T.; Miura, M. J. Am. Chem. Soc. 2010, 132, 6900
29. Cho, S. H.; Kim, J. Y.; Lee, S. Y.; Chang, S. Angew. Chem., Int. Ed. 2009, 48, 9127
30. Kim, J. Y.; Cho, S. H.; Joseph, J.; Chang, S. Angew. Chem., Int. Ed. 2010, 49, 9899
31. Wang, H. F.; Li, Y. M.; Sun, F. F.; Feng, Y.; Jin, K.; Wang, X. N. J. Org. Chem. 2008, 73, 8639
32. Li, Y.; Wang, H.; Jiang, L.; Sun, F.; Fu, X.; Duan, C. Eur. J. Org. Chem. 2010, 6967
33. Guo, S.; Qian, B.; Xie, Y.; Xia, C.; Huang, H. Org. Lett. 2011, 13, 522
34. Lewis, E. A.; Tolman, W. B. Chem. Rev. 2004, 104, 1047
35. Kunishita, A.; Ishimaru, H.; Nakashima, S.; Ogura, T.; Itoh, S. J. Am. Chem. Soc. 2008, 130, 4244
36. Zhang, C.; Jiao, N. Angew. Chem., Int. Ed. 2010, 49, 6174
37. Cioffi, C. L.; Lansing, J. J.; Yuksel, H. J. Org. Chem. 2010, 75, 7942
38. Masatoshi, Y.; Yasuo, T.; Kyoto, H.; Kuniko, H. Chem. Pharm. Bull. 1984, 32, 3053