Cobalt- and manganese-catalyzed direct amination of azoles under mild reaction conditions and the mechanistic details

Angewandte Chemie - International Edition

Volumn 49, Issue 51, 2010, Pages 9899-9903

  Kim, Ji Young ^a   Cho, Seung Hwan ^a   Joseph, Jomy ^a   Chang, Sukbok ^a  

^a Korea Advanced Institute of Science and Technology (KAIST)   (South Korea)

Author keywords

amination; cobalt; heterocycles; manganese; peroxides

Indexed keywords

ACID ADDITIVES; BIOLOGICAL ACTIVITIES; CATALYST LOADINGS; DIRECT AMINATION; HETEROCYCLES; MILD REACTION CONDITIONS; OPTIMAL REACTION CONDITION; PHARMACOPHORES; SECONDARY AMINES;

AMINATION; CATALYSIS; COBALT; MANGANESE; OXIDATION; PEROXIDES;

AMINES;

AMINE; COBALT; DRUG; MANGANESE; PEROXIDE; PYRROLE DERIVATIVE;

AMINATION; ARTICLE; CATALYSIS; CHEMISTRY; SYNTHESIS;

AMINATION; AMINES; AZOLES; CATALYSIS; COBALT; MANGANESE; PEROXIDES; PHARMACEUTICAL PREPARATIONS;

EID: 78650279320     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201005922     Document Type: Article

References (59)

1. R. Hili, A. K. Yudin, Nat. Chem. Biol. 2006, 2, 284
2. Amino Group Chemistry, From Synthesis to the Life Sciences (Ed.:, A. Ricci,), Wiley-VCH, Weinheim, 2007.
3. For recent reviews on copper-mediated N-arylation reactions, see
4. S. V. Ley, A. W. Thomas, Angew. Chem. 2003, 115, 5558
5. Angew. Chem. Int. Ed. 2003, 42, 5400
6. G. Evano, N. Blanchard, M. Toumi, Chem. Rev. 2008, 108, 3054.
7. D. S. Surry, S. L. Buchwald, Angew. Chem. 2008, 120, 6438
8. Angew. Chem. Int. Ed. 2008, 47, 6338
9. J. F. Hartwig, Acc. Chem. Res. 2008, 41, 1534.
10. M. Kim, S. Chang, Org. Lett. 2010, 12, 1640.
11. P. Y. S. Lam, S. Deudon, K. M. Averill, R. Li, M. Y. He, P. DeShong, C. G. Clark, J. Am. Chem. Soc. 2000, 122, 7600
12. J. P. Collman, M. Zhong, Org. Lett. 2000, 2, 1233
13. H. Rao, H. Fu, Y. Jiang, Y. Zhao, Angew. Chem. 2009, 121, 1134
14. Angew. Chem. Int. Ed. 2009, 48, 1114.
15. F. Collet, R. H. Dodd, P. Dauban, Chem. Commun. 2009, 5061.
16. P. Müller, C. Fruit, Chem. Rev. 2003, 103, 2905
17. P. Dauban, R. H. Dodd, Synlett 2003, 1571
18. H. M. L. Davies, J. R. Manning, Nature 2008, 451, 417.
19. W. C. P. Tsang, N. Zheng, S. L. Buchwald, J. Am. Chem. Soc. 2005, 127, 14560
20. B.-J. Li, S.-L. Tian, Z. Fang, Z.-J. Shi, Angew. Chem. 2008, 120, 1131
21. Angew. Chem. Int. Ed. 2008, 47, 1115
22. J. A. Jordan-Hore, C. C. C. Johansson, M. Gulias, E. M. Beck, M. J. Gaunt, J. Am. Chem. Soc. 2008, 130, 16184
23. T.-S. Mei, X. Wang, J.-Q. Yu, J. Am. Chem. Soc. 2009, 131, 10806.
24. X. Chen, X.-S. Hao, C. E. Goodhue, J.-Q. Yu, J. Am. Chem. Soc. 2006, 128, 6790
25. H.-Y. Thu, W.-Y. Yu, C.-M. Che, J. Am. Chem. Soc. 2006, 128, 9048.
26. T. Hamada, X. Ye, S. S. Stahl, J. Am. Chem. Soc. 2008, 130, 833
27. A. E. King, L. M. Huffman, A. Casitas, M. Costas, X. Ribas, S. S. Stahl, J. Am. Chem. Soc. 2010, 132, 12068.
28. A. Armstrong, J. C. Collins, Angew. Chem. 2010, 122, 2332
29. Angew. Chem. Int. Ed. 2010, 49, 2282.
30. D. Monguchi, T. Fujiwara, H. Furukawa, A. Mori, Org. Lett. 2009, 11, 1607
31. Q. Wang, S. L. Schreiber, Org. Lett. 2009, 11, 5178.
32. T. Kawano, K. Hirano, T. Satoh, M. Miura, J. Am. Chem. Soc. 2010, 132, 6900.
33. S. Ko, Y. Na, S. Chang, J. Am. Chem. Soc. 2002, 124, 750
34. J. M. Lee, Y. Na, H. Han, S. Chang, Chem. Soc. Rev. 2004, 33, 302
35. S. H. Cho, S. J. Hwang, S. Chang, J. Am. Chem. Soc. 2008, 130, 9254
36. S. J. Hwang, S. H. Cho, S. Chang, J. Am. Chem. Soc. 2008, 130, 16158
37. M. Kim, J. Kwak, S. Chang, Angew. Chem. 2009, 121, 9097
38. Angew. Chem. Int. Ed. 2009, 48, 8935
39. S. H. Kim, S. Chang, Org. Lett. 2010, 12, 1868
40. J. Kim, S. Chang, J. Am. Chem. Soc. 2010, 132, 10272.
41. S. H. Cho, J. Y. Kim, S. Y. Lee, S. Chang, Angew. Chem. 2009, 121, 9291
42. Angew. Chem. Int. Ed. 2009, 48, 9127.
43. S. Chiba, Z. Cao, S. A. A. E. Bialy, K. Narasaka, Chem. Lett. 2006, 35, 18
44. I. B. Seiple, S. Su, R. A. Rodriguez, R. Gianatassio, Y. Fujiwara, A. L. Sobel, P. S. Baran, J. Am. Chem. Soc. 2010, 132, 13194.
45. E. J. Y. Scott, J. Phys. Chem. 1970, 74, 1174
46. R. P. Houghton, C. R. Rice, Polyhedron 1996, 15, 1893.
47. N. A. Johnson, E. S. Gould, J. Am. Chem. Soc. 1973, 95, 5198
48. D. T. Sawyer, A. Sobkowiak, T. Matsushita, Acc. Chem. Res. 1996, 29, 409.
49. A similar result was obtained in the Ag-mediated amination reaction of benzothiazoles (Refa [15]). Additional investigations on the effects of Lewis acid additives are now underway.
50. H. L. Yale, K. Losee, J. Med. Chem. 1966, 9, 478
51. S. A. F. Rostom, M. A. Shalaby, M. A. El-Demellawy, Eur. J. Med. Chem. 2003, 38, 959.
52. The direct amination with 1-methylbenzimidazole or 4,5-dimethylthiazole was unsuccessful under Co or Mn catalysis conditions, and the starting materials were recovered unchanged.
53. See the Supporting Information for details.
54. Analogous to the putative 2-aminobenzoxazolidine intermediate 7, oxidation of carbinolamine or hemiacetal species by metal/peroxide oxidant systems has been invoked for the oxidative amidation or esterification of aldehydes with amines or alcohols
55. R. Gopinath, B. K. Patel, Org. Lett. 2000, 2, 577
56. W.-J. Yoo, C.-J. Li, J. Am. Chem. Soc. 2006, 128, 13064
57. K. Ekoue-Kovi, C. Wolf, Org. Lett. 2007, 9, 3429.
58. Y.-X. Chen, L.-F. Qian, W. Zhang, B. Han, Angew. Chem. 2008, 120, 9470
59. Angew. Chem. Int. Ed. 2008, 47, 9330.