Ru(II)-catalyzed ortho-C-H amination of arenes and heteroarenes at room temperature

Organic Letters

Volumn 15, Issue 20, 2013, Pages 5286-5289

  Shang, Ming ^a   Zeng, Shao Hang ^a   Sun, Shang Zheng ^a   Dai, Hui Xiong ^a   Yu, Jin Quan ^a,b  

^a SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

^b SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; AMINE; AROMATIC HYDROCARBON; ORGANOMETALLIC COMPOUND; RUTHENIUM;

AMINATION; ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; CHEMISTRY; SYNTHESIS; TEMPERATURE;

AMIDES; AMINATION; AMINES; CATALYSIS; HYDROCARBONS, AROMATIC; MOLECULAR STRUCTURE; ORGANOMETALLIC COMPOUNDS; RUTHENIUM; TEMPERATURE;

EID: 84886241810     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol402515s     Document Type: Article

References (42)

1. Hili, R.; Yudin, A. K. Nat. Chem. Biol. 2006, 2, 284
2. Amino Group Chemistry, From Synthesis to the Life Sciences; Ricci, A., Ed.; Wiley-VCH: Weinheim, 2007.
3. Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534
4. Surry, D. S.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 6338
5. Tsang, W. C. P.; Zheng, N.; Buchwald, S. L. J. Am. Chem. Soc. 2005, 127, 14560
6. Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 14058
7. Jordan-Hore, J. A.; Johansson, C. C. C.; Gulias, M.; Beck, E. M.; Gaunt, M. J. Am. Chem. Soc. 2008, 130, 16184
8. Mei, T.-S.; Wang, X.; Yu, J.-Q. J. Am. Chem. Soc. 2009, 131, 10806
9. Neumann, J.; Rakshit, S.; Dröge, T.; Glorius, F. Angew. Chem., Int. Ed. 2009, 48, 6892
10. Tan, Y.; Hartwig, J. F. J. Am. Chem. Soc. 2010, 132, 3676
11. Nadres, E. T.; Daugulis, O. J. Am. Chem. Soc. 2012, 134, 7
12. He, G.; Zhao, Y.; Zhang, S.; Lu, C.; Chen, G. J. Am. Chem. Soc. 2012, 134, 3
13. For Pd-catalyzed intermolecular C-H amination with alkylamines, see: Yoo, E. J.; Ma, S.; Mei, T.-S.; Chan, K. S. L.; Yu, J.-Q. J. Am. Chem. Soc. 2011, 133, 7652
14. Thu, H.-Y.; Yu, W.-Y.; Che, C.-M. J. Am. Chem. Soc. 2006, 128, 9048
15. Ng, K.-H.; Chan, A. S. C.; Yu, W.-Y. J. Am. Chem. Soc. 2010, 132, 12862
16. Xiao, B.; Gong, T.-J.; Xu, J.; Liu, Z.-J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 1466
17. Sun, K.; Li, Y.; Xiong, T.; Zhang, J.; Zhang, Q. J. Am. Chem. Soc. 2011, 133, 1694
18. Xiao, B.; Gong, T.-J.; Xu, J.; Liu, Z.-J.; Liu, L. J. Am. Chem. Soc. 2011, 133, 1466
19. Sun, K.; Li, Y.; Xiong, T.; Zhang, J.; Zhang, Q. J. Am. Chem. Soc. 2011, 133, 1694
20. Rosen, B. R.; Simke, L. R.; Thuy-Boun, P. S.; Dixon, D. D.; Yu, J.-Q.; Baran, P. S. Angew. Chem., Int. Ed. 2013, 52, 7458
21. Ng, K.-H.; Zhou, Z.; Yu, W.-Y. Org. Lett. 2012, 14, 272
22. Grohmann, C.; Wang, H.; Glorius, F. Org. Lett. 2012, 14, 656
23. Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6790
24. Uemura, T.; Imoto, S.; Chatani, N. Chem. Lett. 2006, 35, 842
25. Brasche, G.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 1932
26. Wang, Q.; Schreiber, S. L. Org. Lett. 2009, 11, 5178
27. Kawano, T.; Hirano, K.; Satoh, T.; Miura, M. J. Am. Chem. Soc. 2010, 132, 6900
28. Wang, H.; Wang, Y.; Peng, C.; Zhang, J.; Zhu, Q. J. Am. Chem. Soc. 2010, 132, 13217
29. Cho, S. H.; Yoon, J.; Chang, S. J. Am. Chem. Soc. 2011, 133, 5996
30. Tran, L. D.; Roane, J.; Daugulis, O. Angew. Chem., Int. Ed. 2013, 52, 6043
31. For a cobalt-catalyzed C-H amination of azoles via acid-promoted nucleophilic attack, see: Kim, J. Y.; Cho, S. H.; Joseph, J.; Chang, S. Angew. Chem., Int. Ed. 2010, 49, 9899
32. Li, B.; Dixneuf, P. H. Chem. Soc. Rev. 2013, 42, 5744
33. Ackermann, L. Acc. Chem. Res. 2013, 46, DOI: 10.1021/ar3002798.
34. Arockiam, P. B.; Bruneau, C.; Dixneuf, P. H. Chem. Rev. 2012, 112, 5879
35. Ackermann, L.; Vicente, R. Top. Curr. Chem. 2010, 292, 211
36. Ackermann, L.; Vicente, R.; Potukuchi, H. K.; Pirovano, V. Org. Lett. 2010, 12, 5032
37. Flegeau, E. F.; Bruneau, C.; Dixneuf, P. H.; Jutand, A. J. Am. Chem. Soc. 2011, 133, 10161
38. Berman, A. M.; Johnson, J. S. J. Am. Chem. Soc. 2004, 126, 5680
39. Berman, A. M.; Johnson, J. S. Synlett 2005, 1799
40. Berman, A. M.; Johnson, J. S.; Nora, G.; Miller, M. J. Org. Synth. 2006, 83, 31
41. Berman, A. M.; Johnson, J. S. J. Org. Chem. 2006, 71, 219
42. Campbell, M. J.; Johnson, J. S. Org. Lett. 2007, 9, 1521