Copper-catalyzed aliphatic C-H amination with an amidine moiety

Organic Letters

Volumn 15, Issue 1, 2013, Pages 212-215

  Chen, Hui ^a   Sanjaya, Stephen ^a   Wang, Yi Feng ^a   Chiba, Shunsuke ^a  

^a Nanyang Technological University   (Singapore)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDINE; AMINE; COPPER; DIAMINE; IMIDAZOLE DERIVATIVE;

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

AMIDINES; AMINATION; AMINES; CATALYSIS; COPPER; DIAMINES; IMIDAZOLES; MOLECULAR STRUCTURE;

EID: 84874084114     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol303302r     Document Type: Article

References (55)

1. Thomas, G. L.; Johannes, C. W. Curr. Opin. Chem. Biol. 2011, 15, 516.
2. Tohme, R.; Darwiche, N.; Gali-Muhtasib, H. Molecules 2011, 16, 9665.
3. Dandapani, S.; Marcaurelle, L. A. Curr. Opin. Chem. Biol. 2010, 14, 362.
4. Welsch, M. E.; Snyder, S. A.; Stockwell, B. R. Curr. Opin. Chem. Biol. 2010, 14, 347.
5. Carey, J. S.; Laffan, D.; Thomson, C.; Williams, M. T. Org. Biomol. Chem. 2006, 4, 2337.
6. Roizen, J. L.; Harvey, M. E.; Du Bois, J. Acc. Chem. Rec. 2012, 45, 911.
7. Du Bois, J. Org. Process Res. Dev. 2011, 15, 758.
8. Collet, F.; Lescot, C.; Dauban, P. Chem. Soc. Rev. 2011, 40, 1926.
9. Zalatan, D. N.; Du Bois, J. Top. Curr. Chem. 2010, 292, 347.
10. Collet, F.; Dodd, R. H.; Dauban, P. Chem. Commun. 2009, 5061.
11. Di'az-Requejo, M. M.; Pérez, P. J. Chem. Rev. 2008, 108, 3379.
12. Wiese, S.; McAfee, J. L.; Pahls, D. R.; McMillin, C. L.; Cundari, T. R.; Warren, T. H. J. Am. Chem. Soc. 2012, 134, 10114.
13. Nguyen, Q.; Sun, K.; Driver, T. G. J. Am. Chem. Soc. 2012, 134, 7262.
14. Paradine, S. M.; White, M. C. J. Am. Chem. Soc. 2012, 134, 2036.
15. Lebel, H.; Trudel, C.; Spitz, C. Chem. Commun. 2012, 48, 7799.
16. Harvey, M. E.; Musaev, D. G.; Du Bois, J. J. Am. Chem. Soc. 2011, 133, 17207.
17. Lyaskovskyy, V.; Olivos Suarez, A. I.; Lu, H.; Jiang, H.; Zhang, X. P.; de Bruin, B. J. Am. Chem. Soc. 2011, 133, 12264.
18. King, E. R.; Hennessy, E. T.; Betley, T. A. J. Am. Chem. Soc. 2011, 133, 4917.
19. Ichinnose, M.; Suematsu, H.; Yasutomi, Y.; Nishioka, Y.; Uchida, T.; Katsuki, T. Angew. Chem., Int. Ed. 2011, 50, 9884.
20. Lu, H.; Jiang, H.; Wojtas, L.; Zhang, X. P. Angew. Chem., Int. Ed. 2010, 49, 10192.
21. Wiese, S.; Badiei, Y. M.; Gephart, R. T.; Mossin, S.; Varonka, M. S.; Melzer, M. M.; Meyer, K.; Cundari, T. R.; Warren, T. H. Angew. Chem., Int. Ed. 2010, 49, 8850.
22. Lu, H.; Tao, J.; Jones, J. E.; Wojtas, L.; Zhang, X. P. Org. Lett. 2010, 12, 1248 and references therein. For reports on the transition-metal-free nitrene transfer reactions for aliphatic CHamination (amidation)
23. Ochiai, M.; Miyamoto, K.; Kaneaki, T.; Hayashi, S.; Nakanishi, W. Science 2011, 332, 448.
24. Bettinger, H. F.; Filthaus, M.; Bornemann, H.; Oppel, I.M. Angew. Chem., Int. Ed. 2008, 47, 4744.
25. Jiang, C.; Covell, D. J.; Stepan, A. F.; Plummer, M. S.; White, M. C. Org. Lett. 2012, 14, 1386.
26. Qi, X.; Rice, G. T.; Lall, M. S.; Plummer, M. S.; White, M. C. Tetrahedron 2010, 66, 4816.
27. Shimizu, Y.; Obora, Y.; Ishii, Y. Org. Lett. 2010, 12, 1372.
28. Rice, G. T.; White, M. C. J. Am. Chem. Soc. 2009, 131, 11707.
29. Reed, S. A.; Mazzotti, A. R.; White, M. C. J. Am. Chem. Soc. 2009, 131, 11701.
30. Nahra, F.; Liron, F.; Prestat, G.; Mealli, C.; Messaoudi, A.; Poli, G. Chem.-Eur. J 2009, 15, 11078 and references therein. Very recently, Brewer reported stereospecific intramolecular CH amination of 1-aza-2-azoniaallene salts
31. Bercovici, D. A.; Brewer, M. J. Am. Chem. Soc. 2012, 134, 9890.
32. Titouania, S. L.; Lavergne, J.-P.; Viallefonta, P.; Jacquierb, E. Tetrahedron 1980, 36, 2961.
33. Corey, E. J.; Hertler, W. R. J. Am. Chem. Soc. 1960, 82, 1657.
34. Löffler, K.; Freytag, C. Ber. 1909, 42, 3427.
35. Hofmann, A. W. Ber. 1883, 16, 558.
36. Amaoka, Y.; Kamijo, S.; Hoshikawa, T.; Inoue, M. J. Org. Chem. 2012, 77, 9959.
37. Michaudel, Q.; Thevenet, D.; Baran, P. S. J. Am. Chem. Soc. 2012, 134, 2547.
38. Ni, Z.; Zhang, Q.; Xiong, T.; Zheng, Y.; Li, Y.; Zhang, H.; Zhang, J.; Liu, Q. Angew. Chem., Int. Ed. 2012, 51, 1244.
39. Gephart, R. T., III; Huang, D. L.; Aguila, M. J. B.; Schmidt, G.; Shahu, A.; Warren, T. H. Angew. Chem., Int. Ed. 2012, 51, 6488.
40. Sakagushi, S.; Hirabayashi, T.; Ishii, Y. Chem. Commun. 2002, 516.
41. Togo, H.; Harada, Y.; Yokoyama, M. J. Org. Chem. 2000, 65, 926.
42. Sanjaya, S.; Chiba, S. Org. Lett. 2012, 14, 5342.
43. Wang, Y.-F.; Chen, H.; Zhu, X.; Chiba, S. J. Am. Chem. Soc. 2012, 134, 11980.
44. Wang, Y.-F.; Zhu, X.; Chiba, S. J. Am. Chem. Soc. 2012, 134, 3679.
45. Cekovic, Z. Tetrahdron 2003, 59, 8073.
46. Majetich, G.; Wheless, K. Tetrahedron 1995, 51, 7095.
47. Kochi, J. K.; Bemis, A.; Jenkins, C. L. J. Am. Chem. Soc. 1968, 90, 4616.
48. Kizirian, J.-C. Chem. Rev. 2008, 108, 140.
49. Kotti, S. R. S. S.; Timmons, C.; Li, G. Chem. Biol. Drug Des. 2006, 67, 101.
50. Viso, A.; de la Pradilla, R. F.; Garci'a, A.; Flores, A. Chem. Rev. 2005, 105, 3167.
51. de Parrodi, C. A.; Juaristi, E. Synlett 2006, 17, 2699.
52. Lucet, D.; Gall, T. L.; Mioskowski, C. Angew. Chem., Int. Ed. 1998, 37, 2580.
53. Brown, H. C.; Yoon, N. M. J. Am. Chem. Soc. 1966, 88, 1464.
54. Dal Maso, M.; Orelli, L.; Perillo, I. A. J. Heterocycl. Chem. 1994, 31, 25.
55. Dunn, P. J. In Comprehensive Organic Functional Group Transformations II; Elsevier: Oxford, U.K., 2005; Vol. 5, pp 655-699.