Aerobic oxidative transformation of primary alcohols and amines to amides promoted by a hydroxyapatite-supported gold catalyst in water

Tetrahedron Letters

Volumn 55, Issue 1, 2014, Pages 124-127

  Wang, Wentao ^a   Cong, Yu ^a   Zhang, Leilei ^a   Huang, Yanqiang ^a   Wang, Xiaodong ^a   Zhang, Tao ^a  

^a DALIAN INSTITUTE OF CHEMICAL PHYSICS   (China)

Author keywords

Aerobic oxidation; Amides; Gold; Heterogeneous catalyst

Indexed keywords

ALCOHOL DERIVATIVE; AMIDE; AMINE; GOLD; HYDROXYAPATITE; WATER;

ARTICLE; CATALYST; OXIDATION;

EID: 84890165921     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2013.10.133     Document Type: Article

References (48)

1. G. Arthur The Amide Linkage: Selected Structural Aspects in Chemistry, Biochemistry, and Materials Science 2000 Wiley-Interscience
2. C.A.G.N. Montalbetti, and V. Falque Tetrahedron 61 2005 10827 10852
3. E. Valeur, and M. Bradley Chem. Soc. Rev. 38 2009 606 631
4. For reviews, see: (a) V.R. Pattabiraman, and J.W. Bode Nature 480 2011 471 479
5. C.L. Allen, and J.M.J. Williams Chem. Soc. Rev. 40 2011 3405 3415
6. C. Chen, and S.H. Hong Org. Biomol. Chem. 9 2011 20 26
7. S. Roy, and G.W. Gribble Tetrahedron 68 2012 9867 9923
8. C. Singh, V. Kumar, U. Sharma, N. Kumar, and B. Singh Curr. Org. Synth. 10 2013 241 264
9. K. Yamaguchi, and N. Mizuno Synlett 2010 2365 2382 and references cited therein
10. S.K. Klitgaard, K. Egelblad, U.V. Mentzel, A.G. Popov, T. Jensen, E. Taarning, I.S. Nielsen, and C.H. Christensen Green Chem. 10 2008 419 423
11. Y. Wang, D.P. Zhu, L. Tang, S.J. Wang, and Z.Y. Wang Angew. Chem., Int. Ed. 50 2011 8917 8921
12. J.F. Soulé, H. Miyamura, and S. Kobayashi J. Am. Chem. Soc. 133 2011 18550 18553
13. K. Yamaguchi, H. Kobayashi, T. Oishi, and N. Mizuno Angew. Chem., Int. Ed. 51 2012 544 547
14. S. Kegnæs, J. Mielby, U.V. Mentzel, T. Jensen, P. Fristrup, and A. Riisager Chem. Commun. 2012 2427 2429
15. T. Ishida, H. Watanabe, T. Takei, A. Hamasaki, M. Tokunaga, and M. Haruta Appl. Catal. A: Gen. 425 2012 85 90
16. J. Mielby, A. Riisager, P. Fristrup, and S. Kegnaes Catal. Today 203 2013 211 216
17. X.Y. Liu, and K.F. Jensen Green Chem. 15 2013 1538 1541
18. L.L. Zhang, W.T. Wang, A.Q. Wang, Y.T. Cui, X.F. Yang, Y.Q. Huang, X.Y. Liu, W.G. Liu, J.Y. Son, H. Oji, and T. Zhang Green Chem. 15 2013 2680 2684
19. For reviews, see: (a) M. Haruta Nature 437 2005 1098 1099
20. A.S.K. Hashmi, and G.J. Hutchings Angew. Chem., Int. Ed. 45 2006 7896 7936
21. A. Corma, and H. Garcia Chem. Soc. Rev. 37 2008 2096 2126
22. C. Della Pina, C. Della Pina, E. Falletta, L. Prati, and M. Rossi Chem. Soc. Rev. 37 2008 2077 2095
23. Y. Zhang, X.J. Cui, F. Shi, and Y.Q. Deng Chem. Rev. 112 2012 2467 2505
24. M. Stratakis, and H. Garcia Chem. Rev. 112 2012 4469 4506
25. M. Pan, A.J. Brush, Z.D. Pozun, H.H. Ham, W.Y. Yu, G. Henkelman, G.S. Hwang, and C.B. Mullins Chem. Soc. Rev. 42 2013 5002 5013 and references cited therein
26. W.J. Li, A.Q. Wang, X.F. Yang, Y.Q. Huang, and T. Zhang Chem. Commun. 2012 9183 9185
27. W.J. Li, A.Q. Wang, X.Y. Liu, and T. Zhang Appl. Catal. A: Gen. 433 2012 146 151
28. L. Li, A.Q. Wang, B.T. Qiao, J. Lin, Y.Q. Huang, X.D. Wang, and T. Zhang J. Catal. 299 2013 90 100
29. K.F. Zhao, B.T. Qiao, J.H. Wang, Y.J. Zhang, and T. Zhang Chem. Commun. 2011 1779 1781
30. X.F. Yang, A.Q. Wang, Y.L. Wang, T. Zhang, and J. Li J. Phys. Chem. C 114 2010 3131 3139
31. H. Sun, F.Z. Su, J. Ni, Y. Cao, H.Y. He, and K.N. Fan Angew. Chem., Int. Ed. 48 2009 4390 4393
32. T. Mitsudome, A. Noujima, T. Mizugaki, K. Jitsukawa, and K. Kaneda Chem. Commun. 2009 5302 5304
33. Y. Mikami, A. Noujima, T. Mitsudome, T. Mizugaki, K. Jitsukawa, and K. Kaneda Chem. Eur. J. 17 2011 1768 1772 And the synthetical details of Au/HAP were shown in the Supplementary data
34. The base and oxygen were clearly indispensable in this catalytic system. It is well known that NaOH mainly fulfilled two roles: first, it facilitated the cleavage of O-H bond to yield the reactive alkoxide intermediate; second, it promoted the subsequent break of C-H bond of alkoxide intermediate to form aldehyde species and amides on Au nanoparticles. The hydrogen atoms adsorbed over the gold surface can be oxidized by oxygen to give water. Subsequently, the catalytic activity of Au nanoparticles was restored. A number of experimental results and theoretical calculations have indeed confirmed the roles of NaOH and oxygen. (a) A. Abad, A. Corma, and H. Garcia Chem. Eur. J. 14 2008 212 222
35. M. Conte, H. Miyamura, S. Kobayashi, and V. Chechik J. Am. Chem. Soc. 131 2009 7189 7196
36. T. Mitsudome, A. Noujima, T. Mizugaki, K. Jitsukawa, and K. Kaneda Adv. Synth. Catal. 351 2009 1890 1896
37. B. Jorgensen, S.E. Christiansen, M.L.D. Thomsen, and C.H. Christensen J. Catal. 251 2007 332 337
38. J.L. Gong, and C.B. Mullins J. Am. Chem. Soc. 130 2008 16458 16459
39. B.N. Zope, D.D. Hibbitts, M. Neurock, and R.J. Davis Science 330 2010 74 78
40. A.M. Argo, J.F. Odzak, and B.C. Gates J. Am. Chem. Soc. 125 2003 7107 7115
41. H. Tsunoyama, H. Sakurai, Y. Negishi, and T. Tsukuda J. Am. Chem. Soc. 127 2005 9374 9375
42. H. Tsunoyama, H. Sakurai, and T. Tsukuda Chem. Phys. Lett. 429 2006 528 532
43. Y. Yamane, X.H. Liu, A. Hamasaki, T. Ishida, M. Haruta, T. Yokoyama, and M. Tokunaga Org. Lett. 11 2009 5162 5165
44. C. Shang, and Z.P. Liu J. Am. Chem. Soc. 133 2011 9938 9947
45. Y. Kwon, S.C.S. Lai, P. Rodriguez, and M.T.M. Koper J. Am. Chem. Soc. 133 2011 6914 6917
46. T. Ishida, and M. Haruta ChemSusChem 2 2009 538 541
47. B.J. Xu, R.J. Madix, and C.M. Friend Chem. Eur. J. 18 2012 2313 2318
48. C.G.F. Siler, B.J. Xu, R.J. Madix, and C.M. Friend J. Am. Chem. Soc. 134 2012 12604 12610