Direct amination of azoles via catalytic C-H, N-H Coupling

Organic Letters

Volumn 11, Issue 7, 2009, Pages 1607-1610

  Monguchi, Daiki ^a   Fujiwara, Taiki ^a   Furukawa, Hirotoshi ^a   Mori, Atsunori ^a  

^a KOBE UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 64349114690     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol900298e     Document Type: Article

References (62)

1. (a) Kakiuchi, F.; Kochi, T. Synthesis 2008, 3013.
2. (b) Dyker, G. Angew. Chem., Int. Ed. 1999, 38, 1698.
3. (c) Alberico, D.; Scott, M. E.; Lautens, M. Chem. Rev. 2007, 107, 174, and references therein.
4. For reviews, see: (a) Mori, A.; Sugie, A. Bull. Chem. Soc. Jpn. 2008, 81, 548.
5. (b) Campeau, L. C.; Stuart, D. R.; Fagnou, K. Aldrichimica Acta 2007, 40, 35.
6. (c) Zificsak, C. A.; Hlasta, D. J. Tetrahedron 2004, 60, 8991.
7. (d) Satoh, T.; Miura, M. Chem. Lett. 2007, 36, 200.
8. (e) Seregin, I. V.; Gevorgan, V. Chem. Soc. Rev. 2007, 36, 1173, and references therein.
9. (a) Turner, G. L.; Morris, J. A.; Greaney, M. F. Angew. Chem., Int. Ed. 2007, 46, 7996.
10. (b) Bellina, F.; Calandri, C.; Cauteruccio, S.; Rossi, R. Tetrahedron 2007, 63, 1970.
11. (c) Alagille, D.; Baldwin, R. M.; Tamagnan, G. D. Tetrahedron Lett. 2005, 46, 1349.
12. (d) Kondo, Y.; Komine, T.; Sakamoto, T. Org. Lett. 2000, 2, 3111.
13. (e) Gottumukkala, A. L.; Doucet, H. Eur. J. Inorg. Chem. 2007, 23, 3629.
14. (f) Parisien, M.; Valette, D.; Fagnou, K. J. Org. Chem. 2005, 70, 7578.
15. (g) Pivsa-Art, S.; Satoh, T.; Kawamura, Y.; Miura, M.; Nomura, M. Bull. Chem. Soc. Jpn. 1998, 71, 467.
16. (h) Do, H.-Q.; Khan, R. M. K.; Daugulis, O. J. Am. Chem. Soc. 2008, 130, 15185.
17. (a) Mori, A.; Sekiguchi, A.; Masui, K.; Shimada, T.; Horie, M.; Osakada, K.; Kawamoto, M.; Ikeda, T. J. Am. Chem. Soc. 2003, 125, 1700.
18. (b) Kobayashi, K.; Sugie, A.; Takahashi, M.; Masui, K.; Mori, A. Org. Lett. 2005, 7, 5083.
19. (c) Sugie, A.; Kobayashi, K.; Suzaki, Y.; Osakada, K. Chem. Lett. 2006, 35, 1100.
20. (d) Kobayashi, K.; Mohamed Ahmed, M. S.; Mori, A. Tetrahedron 2006, 62, 9548.
21. (e) Takahashi, M.; Masui, K.; Sekiguchi, H.; Kobayashi, N.; Mori, A.; Funahashi, M.; Tamaoki, N. J. Am. Chem. Soc. 2006, 128, 10930.
22. (f) Arai, N.; Takahashi, M.; Mitani, M.; Mori, A. Synlett., 2006, 3170.
23. (g) Mori, A.; Shikuma, J.; Kinoshita, M.; Ikeda, T.; Misaki, M.; Ueda, Y.; Komura, M.; Asaoka, S.; Iyoda, T. Chem. Lett. 2008, 37, 272.
24. (h) Arai, N.; Miyaoku, T.; Teruya, S.; Mori, A. Tetrahedron Lett. 2008, 49, 1000.
25. (i) Miyaoku, T.; Mori, A. Heterocycles 2009, 77, 151.
26. (a) Stuart, D. R.; Fagnou, K. Science 2007, 316, 1172.
27. (b) Dwight, T. A.; Rue, N. R.; Charyk, D.; Josselyn, R.; DeBoef, B. Org. Lett. 2007, 9, 3137.
28. (c) Li, B.-J.; Tian, S.-L.; Fang, Z.; Shi, Z.-J. Angew. Chem., Int. Ed. 2008, 47, 1115.
29. (d) Oi, S.; Sato, H.; Sugawara, S.; Inoue, Y. Org. Lett. 2008, 10, 1823.
30. (e) Ban, I.; Sudo, T.; Taniguchi, T.; Itami, K. Org. Lett. 2008, 10, 3607.
31. (f) Masui, K.; Ikegami, H.; Mori, A. J. Am. Chem. Soc. 2004, 126, 5074.
32. (a) Paul, F.; Patt, J.; Hartwig, J. F. J. Am. Chem. Soc. 1994, 116, 5969.
33. (b) Guram, A. S.; Buchwald, S. L. J. Am. Chem. Soc. 1994, 116, 7901.
34. (c) Yamamoto, T.; Nishiyama, M.; Koie, Y. Tetrahedron Lett. 1998, 39, 2367. For reviews, see:
35. (d) Hartwig, J. F. Acc. Chem. Res. 2008, 41, 1534.
36. (e) Wolfe, J. P.; Wagaw, S.; Marcoux, J.-F.; Buchwald, S. L. Acc. Chem. Res. 1998, 31, 805.
37. (a) Lam, P. Y. S.; Clark, C. G.; Saubern, S.; Adams, J.; Averill, K. M.; Chan, D. M. T.; Combs, A. Synlett., 2000, 5, 674.
38. (b) Lam, P. Y. S.; Deudon, S.; Averill, K. M.; Li, R. H.; He, M. Y.; DeShong, P.; Clark, C. G. J. Am. Chem. Soc. 2000, 122, 7600.
39. (c) Lam, P. Y. S.; Vincent, G.; Bonne, D.; Clark, C. G. Tetrahedron Lett. 2002, 43, 3091.
40. (d) Kwong, F. Y.; Klapars, A.; Buchwald, S. L. Org. Lett. 2002, 4, 581.
41. (e) Collman, J. P.; Zhong, M. Org. Lett. 2000, 2, 1233.
42. (f) Yu, X.-Q.; Yamamoto, Y.; Miyaura, N. Chem. Asian J. 2008, 3, 1517.
43. (a) Brasche, G.; Buchwald, S. L. Angew. Chem., Int. Ed. 2008, 47, 1932.
44. (b) Inamoto, K.; Hasegawa, C.; Hiroya, K.; Doi, T. Org. Lett. 2008, 10, 5147.
45. (c) Thu, H.-Y.; Yu, W.-Y.; Che, C.-M. J. Am. Chem. Soc. 2006, 128, 9048.
46. (d) Wasa, M.; Yu, J.-Q. J. Am. Chem. Soc. 2008, 130, 14058.
47. (e) Lebel, H.; Huard, K.; Lectard, S. J. Am. Chem. Soc. 2005, 127, 14198.
48. (a) Hamada, T.; Ye, X.; Stahl, S. S. J. Am. Chem. Soc. 2008, 130, 833.
49. (b) Chen, X.; Hao, X.-S.; Goodhue, C. E.; Yu, J.-Q. J. Am. Chem. Soc. 2006, 128, 6791.
50. (c) Thu, H.-Y.; Yu, W.-Y.; Che, C.-M. J. Am. Chem. Soc. 2006, 128, 9048.
51. Insertion of a carbene complex into N-H bond: (a) Liang, C.; Collet, F.; Robert-Peillard, F.; Müller, P.; Dodd, R. H.; Dauban, P. J. Am. Chem. Soc. 2008, 130, 343.
52. (b) Fiori, K. W.; Du Bois, J. J. Am. Chem. Soc. 2007, 129, 562.
53. (c) Badiei, Y. M.; Dinescu, A.; Dai, X.; Palomino, R. M.; Heinemann, F. W.; Cundari, T. R.; Warren, T. H. Angew. Chem., Int. Ed. 2008, 47, 9961.
54. (d) Shen, M.; Leslie, B. E.; Driver, T. G. Angew. Chem., Int. Ed. 2008, 47, 5056.
55. (e) Espino, C. G.; Fiori, K. W.; Kim, M.; Du Bois, J. J. Am. Chem. Soc. 2004, 126, 15378.
56. (f) Li, Z.; Capretto, D. A.; Rahaman, R. O.; He, C. J. Am. Chem. Soc. 2007, 129, 12058.
57. (g) Fraunhoffer, K. J.; White, M. C. J. Am. Chem. Soc. 2007, 129, 7275.
58. Furukawa, H.; Matsumura, S.; Sugie, A.; Monguchi, D.; Mori, A. Heterocycles 2009, in press.
59. (a) Masui, K.; Mori, A.; Okano, K.; Takamura, K.; Kinoshita, M.; Ikeda, T. Org. Lett. 2004, 6, 2011.
60. (b) Shikuma, J.; Mori, A.; Masui, K.; Matsuura, R.; Sekiguchi, A.; Ikegami, H.; Kawamoto, M.; Ikeda, T. Chem. Asian J. 2007, 2, 301.
61. No reaction was confirmed to take place by mixing 13 and 2a in xylene at 140 °C for 3 h.
62. The authors thank Nara Institute of Science and Technology, Kyoto-Advanced Nanotechnology Network, supported by MEXT for measurements of high resolution mass spectra.