Selective aerobic oxidation of methanol in the coexistence of amines by nanoporous gold catalysts: Highly efficient synthesis of formamides

Chemistry - A European Journal

Volumn 19, Issue 36, 2013, Pages 11832-11836

  Tanaka, Shinya ^a   Minato, Taketoshi ^a,b   Ito, Eisuke ^b   Hara, Masahiko ^b,c   Kim, Yousoo ^b   Yamamoto, Yoshinori ^a,d   Asao, Naoki ^a  

^a TOHOKU UNIVERSITY   (Japan)

^b RIKEN   (Japan)

^c TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^d DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

chemoselectivity; gold; heterogeneous catalysis; nanoporous material; oxidation

Indexed keywords

AEROBIC OXIDATIONS; ALKYL AMINES; AU-AG ALLOYS; CHEMO-SELECTIVITY; EFFICIENT SYNTHESIS; NANO-POROUS MATERIALS; NANOPOROUS GOLD; SYNERGISTIC EFFECT;

AMINES; CATALYSIS; CATALYSTS; METHANOL; OXIDATION; POROUS MATERIALS; SILVER;

GOLD;

EID: 84883231110     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201302396     Document Type: Article

References (57)

1. T. Mallat, A. Baiker, Chem. Rev. 2004, 104, 3037-3058
2. B.-Z. Zhan, A. Thompson, Tetrahedron 2004, 60, 2917-2935
3. A. Abad, P. Concepciõn, A. Corma, H. García, Angew. Chem. 2005, 117, 4134-4137
4. Angew. Chem. Int. Ed. 2005, 44, 4066-4469
5. M. J. Schultz, M. S. Sigman, Tetrahedron 2006, 62, 8227-8241
6. T. Matsumoto, M. Ueno, N. Wang, S. Kobayashi, Chem. Asian J. 2008, 3, 196-214
7. C. P. Vinod, K. Wilson, A. F. Lee, J. Chem. Technol. Biotechnol. 2011, 86, 161-171
8. A. Corma, A. Leyva-Pérez, M. J. Sabater, Chem. Rev. 2011, 111, 1657-1712
9. C. Parmeggiani, F. Cardona, Green Chem. 2012, 14, 547-564.
10. Review:, M. T. Schümperli, C. Hammond, I. Hermans, ACS Catal. 2012, 2, 1108-1117.
11. D. Milstein, Top. Catal. 2010, 53, 915-923
12. C. Chen, S. H. Hong, Org. Biomol. Chem. 2011, 9, 20-26
13. C. L. Allen, J. M. J. Williams, Chem. Soc. Rev. 2011, 40, 3405-3415.
14. S. K. Klitgaard, K. Egeblad, U. V. Mentzel, A. G. Popov, T. Jensen, E. Taarning, I. S. Nielsen, C. H. Christensen, Green Chem. 2008, 10, 419-423.
15. S. Kegnæs, J. Mielby, U. V. Mentzel, T. Jensen, P. Fristrup, A. Riisager, Chem. Commun. 2012, 48, 2427-2429.
16. J. Mielby, S. Kegnaes, P. Fristrup, ChemCatChem 2012, 4, 1037-1047
17. H. Miyamura, S. Kobayashi, J. Am. Chem. Soc. 2011, 133, 2840
18. Y. Wang, D. Zhu, L. Tang, S. Wang, Z. Wang, Angew. Chem. 2011, 123, 9079-9083
19. Angew. Chem. Int. Ed. 2011, 50, 8917-8921
20. T. Ishida, M. Haruta, ChemSusChem 2009, 2, 538-541
21. P. Preedasuriyachai, H. Kitahara, W. Chavasiri, H. Sakurai, Chem. Lett. 2010, 39, 1174-1176
22. K. Yamaguchi, H. Kobayashi, T. Oishi, N. Mizuno, Angew. Chem. 2012, 124, 559-562
23. Angew. Chem. Int. Ed. 2012, 51, 544-547
24. T. Ishida, H. Watanabe, T. Takei, A. Hamasaki, M. Tokunaga, M. Haruta, Appl. Catal. A 2012, 425-426, 85-90.
25. Review:, A. Wittstock, A. Wichmann, M. Bäumer, ACS Catal. 2012, 2, 2199-2215.
26. N. Asao, Y. Ishikawa, N. Hatakeyama, Menggenbateer, Y. Yamamoto, M. Chen, W. Zhang, A. Inoue, Angew. Chem. 2010, 122, 10291-10293
27. Angew. Chem. Int. Ed. 2010, 49, 10093-10095
28. N. Asao, Menggenbateer, Y. Seya, Y. Yamamoto, M. Chen, W. Zhang, A. Inoue, Synlett 2012, 66-69
29. N. Asao, N. Hatakeyama, Menggenbateer, T. Minato, E. Ito, M. Hara, Y. Kim, Y. Yamamoto, M. Chen, W. Zhang, A. Inoue, Chem. Commun. 2012, 48, 4540-4542
30. N. Asao, T. Jin, S. Tanaka, Y. Yamamoto, Pure Appl. Chem. 2012, 84, 1771-1784
31. M. Yan, T. Jin, Y. Ishikawa, T. Minato, T. Fujita, L.-Y. Chen, M. Bao, N. Asao, M.-W. Chen, Y. Yamamoto, J. Am. Chem. Soc. 2012, 134, 17536-17542
32. M. Yan, T. Jin, Q. Chen, H. E. Ho, T. Fujita, L.-Y. Chen, M. Bao, M.-W. Chen, N. Asao, Y. Yamamoto, Org. Lett. 2013, 15, 1484-1487.
33. A. J. Forty, Nature 1979, 282, 597-598
34. R. C. Newman, S. G. Corcoran, J. Erlebacher, M. J. Aziz, K. Sieradzki, MRS Bull. 1999, 24, 24-28
35. J. Erlebacher, M. J. Aziz, A. Karma, N. Dimitrov, K. Sieradzki, Nature 2001, 410, 450-453.
36. S. Kameoka, A. P. Tsai, Catal. Lett. 2008, 121, 337-341.
37. V. Zielasek, B. Jürgens, C. Schulz, J. Biener, M. M. Biener, A. V. Hamza, M. Bäumer, Angew. Chem. 2006, 118, 8421-8425
38. Angew. Chem. Int. Ed. 2006, 45, 8241-8244
39. C. Xu, J. Su, X. Xu, P. Liu, H. Zhao, F. Tian, Y. Ding, J. Am. Chem. Soc. 2007, 129, 42-43.
40. A. Wittstock, V. Zielasek, J. Biener, C. M. Friend, M. Bäumer, Science 2010, 327, 319-322
41. A. Wittstock, A. Wichmann, J. Biener, M. Bäumer, Faraday Discuss. 2011, 152, 87-98
42. K. M. Kosuda, A. Wittstock, C. M. Friend, M. Bäumer, Angew. Chem. 2012, 124, 1730-1733
43. Angew. Chem. Int. Ed. 2012, 51, 1698-1701.
44. Oxidative coupling of methanol and dimethylamine mediated by atomic-oxygen-activated Au(111) under a low temperature (120 K) has been reported, see:, B. Xu, R. J. Madix, C. M. Friend, Chem. Eur. J. 2012, 18, 2313-2318.
45. Z. Zhang, Y. Wang, Z. Qi, J. Lin, X. Bian, J. Phys. Chem. C 2009, 113, 1308-1314
46. Z. Zhang, Y. Wang, Z. Qi, W. Zhang, J. Qin, J. Frenzel, J. Phys. Chem. C 2009, 113, 12629-12636
47. Z. Zhang, Y. Wang, Z. Qi, C. Somsen, X. Wang, C. Zhao, J. Mater. Chem. 2009, 19, 6042-6050.
48. Z. Zhang, Y. Wang, X. Wang, Nanoscale 2011, 3, 1663-1674
49. J. Xu, C. Zhang, X. Wang, H. Ji, C. Zhao, Y. Wang, Z. Zhang, Green Chem. 2011, 13, 1914-1922.
50. X. Wang, J. Sun, C. Zhang, T. Kou, Z. Zhang, J. Phys. Chem. C 2012, 116, 13271-13280.
51. A. Wittstock, B. Neumann, A. Schaefer, K. Dumbuya, C. Kübel, M. M. Biener, V. Zielasek, H.-P. Steinrück, J. M. Gottfried, J. Biener, A. Hamza, M. Bäumer, J. Phys. Chem. C 2009, 113, 5593-5600
52. L. V. Moskaleva, S. Röhe, A. Wittstock, V. Zielasek, T. Klüner, K. M. Neyman, M. Bäumer, Phys. Chem. Chem. Phys. 2011, 13, 4529-4539
53. L. C. Wang, Y. Zhong, D. Widmann, J. Weissmüller, R. J. Behm, ChemCatChem 2012, 4, 251-259.
54. J. S. Hammond, S. W. Gaarenstroom, N. Winograd, Anal. Chem. 1975, 47, 2193-2199
55. J. F. Weaver, G. B. Hoflund, Chem. Mater. 1994, 6, 1693-1699.
56. V. Polshettiwar, R. S. Varma, Green Chem. 2010, 12, 743-754
57. N. Yan, C. Xiao, Y. Kou, Coord. Chem. Rev. 2010, 254, 1179-1218.