Manganese oxide promoted liquid-phase aerobic oxidative amidation of methylarenes to monoamides using ammonia surrogates

Angewandte Chemie - International Edition

Volumn 51, Issue 29, 2012, Pages 7250-7253

  Wang, Ye ^a   Yamaguchi, Kazuya ^a   Mizuno, Noritaka ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

Ammonia; Heterogeneous catalysis; Manganese oxide; Methylarenes; Primary amides

Indexed keywords

AMIDATION; CATALYTIC PERFORMANCE; HIGH YIELD; LIQUID PHASE; METHYL GROUP; METHYLARENES; MONOAMIDES; PRIMARY AMIDES;

AMIDES; AMMONIA; CATALYSIS; FUNCTIONAL GROUPS; OXIDES;

MANGANESE OXIDE;

EID: 84863845185     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201203098     Document Type: Article

References (46)

1. R. A. Sheldon, J. K. Kochi, Metal Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981
2. C. L. Hill, in Advances in Oxygenated Processes, Vol. 1 (Eds.:, A. L. Baumstark,), JAI Press, London, 1988, p. 1
3. M. Hudlucky, Oxidations in Organic Chemistry, ACS Monograph Series, American Chemical Society, Washington, DC, 1990
4. A. Madin, in Comprehensive Organic Synthesis, Vol. 7 (Eds.:, B. M. Trost, I. Fleming, S. V. Ley,), Pergamon, Oxford, 1991, p. 251
5. W. Partenheimer, Catal. Today 1995, 23, 69.
6. L. Kesavan, R. Tiruvalam, M. H. Ab Rahim, M. I. bin Saiman, D. I. Enache, R. L. Jenkins, N. Dimitratos, J. A. Lopez-Sanchez, S. H. Taylor, D. W. Knight, C. J. Kiely, G. J. Hutchings, Science 2011, 331, 195
7. X. Li, J. Xu, L. Zhou, F. Wang, J. Gao, C. Chen, J. Ning, H. Ma, Catal. Lett. 2006, 110, 149
8. F. Wang, J. Xu, X. Li, J. Gao, L. Zhou, R. Ohnishi, Adv. Synth. Catal. 2005, 347, 1987
9. R. L. Brutchey, I. J. Drake, A. T. Bell, T. D. Tilley, Chem. Commun. 2005, 3736.
10. A. Brückner, Catal. Rev. 2003, 45, 97
11. A. Martin, B. Liicke, Catal. Today 1996, 32, 279
12. B. Lücke, K. V. Narayana, A. Martin, K. Jähnisch, Adv. Synth. Catal. 2004, 346, 1407.
13. C. E. Mabermann, in Encyclopedia of Chemical Technology, Vol. 1 (Eds.:, J. I. Kroschwitz,), Wiley, New York, 1991, pp. 251-266
14. D. Lipp, in Encyclopedia of Chemical Technology, Vol. 1 (Eds.:, J. I. Kroschwitz,), Wiley, New York, 1991, p. 266-287
15. R. Opsahl, in Encyclopedia of Chemical Technology, Vol. 2 (Eds.:, J. I. Kroschwitz,), Wiley, New York, 1991, pp. 346-356
16. The Amide Linkage: Structural Significance in Chemistry, Biochemistry and Material Science (Eds.:, A. Greenberg, C. M. Breneman, J. F. Liebman,), Wiley, New York, 2000
17. J. S. Carey, D. Laffan, C. Thomson, M. T. Williams, Org. Biomol. Chem. 2006, 4, 2337.
18. D. J. C. Constable, P. J. Dunn, J. D. Hayler, G. R. Humphrey, J. L. Leazer, Jr., R. J. Linderman, K. Lorenz, J. Manley, B. A. Pearlman, A. Wells, A. Zaks, T. Y. Zhang, Green Chem. 2007, 9, 411
19. E. Valeur, M. Bradley, Chem. Soc. Rev. 2009, 38, 606.
20. C. L. Allen, J. M. J. Williams, Chem. Soc. Rev. 2011, 40, 3405.
21. T. Oshiki, H. Yamashita, K. Sawada, M. Utsunomiya, K. Takahashi, K. Takai, Organometallics 2005, 24, 6287
22. A. Goto, K. Endo, S. Saito, Angew. Chem. 2008, 120, 3663
23. Angew. Chem. Int. Ed. 2008, 47, 3607
24. R. S. Ramõn, N. Marion, S. P. Nolan, Chem. Eur. J. 2009, 15, 8695
25. T. J. Ahmed, S. M. M. Knapp, D. R. Tyler, Coord. Chem. Rev. 2011, 255, 949
26. T. Hirano, K. Uehara, K. Kamata, N. Mizuno, J. Am. Chem. Soc. 2012, 134, 6425
27. T. Mitsudome, Y. Mikami, H. Mori, S. Arita, T. Mizugaki, K. Jitsukawa, K. Kaneda, Chem. Commun. 2009, 3258
28. K. Yamaguchi, M. Matsushita, N. Mizuno, Angew. Chem. 2004, 116, 1602
29. Angew. Chem. Int. Ed. 2004, 43, 1576
30. M. Tamura, H. Wakasugi, K. Shimizu, A. Satsuma, Chem. Eur. J. 2011, 17, 11428.
31. H. Fujiwara, Y. Ogasawara, K. Yamaguchi, N. Mizuno, Angew. Chem. 2007, 119, 5294
32. Angew. Chem. Int. Ed. 2007, 46, 5202
33. N. A. Owston, A. J. Parker, J. M. J. Williams, Org. Lett. 2007, 9, 73
34. M. Kim, J. Lee, H.-Y. Lee, S. Chang, Adv. Synth. Catal. 2009, 351, 1807
35. D. Gnanamgari, R. H. Crabtree, Organometallics 2009, 28, 922
36. R. S. Ramõn, J. Bosson, S. Diez-González, N. Marion, S. P. Nolan, J. Org. Chem. 2010, 75, 1197.
37. K. Yamaguchi, H. Kobayashi, T. Oishi, Angew. Chem. 2012, 124, 559
38. Angew. Chem. Int. Ed. 2012, 51, 544.
39. Y. Wang, H. Kobayashi, K. Yamaguchi, N. Mizuno, Chem. Commun. 2012, 48, 2642
40. J. W. Kim, K. Yamaguchi, N. Mizuno, Angew. Chem. 2008, 120, 9389
41. Angew. Chem. Int. Ed. 2008, 47, 9249.
42. R. A. Sheldon, M. Wallau, I. W. C. E. Arends, U. Schuchardt, Acc. Chem. Res. 1998, 31, 485.
43. N. Nduka, S. Shall, Biochem. Biophys. Res. Commun. 1980, 96, 997
44. L. G. Durrant, G. P. Margison, J. M. Boyle, Carcinogenesis 1981, 2, 1013
45. S. A. Kempson, Am. J. Physiol. 1986, 251, F 520.
46. E. P. Kyba, S. T. Liu, K. Chockalingam, B. R. Reddy, J. Org. Chem. 1988, 53, 3513.