Nanoporous gold catalyst for highly selective semihydrogenation of alkynes: Remarkable effect of amine additives

Journal of the American Chemical Society

Volumn 134, Issue 42, 2012, Pages 17536-17542

  Yan, Mei ^a   Jin, Tienan ^a   Ishikawa, Yoshifumi ^a   Minato, Taketoshi ^a   Fujita, Takeshi ^a   Chen, Lu Yang ^a   Bao, Ming ^b   Asao, Naoki ^a   Chen, Ming Wei ^a   Yamamoto, Yoshinori ^a,b  

^a TOHOKU UNIVERSITY   (Japan)

^b DALIAN UNIVERSITY OF TECHNOLOGY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

3D STRUCTURE; ATOMIC STEP; BICONTINUOUS; CHEMICAL YIELDS; HIGH DENSITY; HYDROGEN ATOMS; HYDROGEN SOURCES; IN-SITU; NANOPOROSITY; NANOPOROUS GOLD; OPTIMIZED REACTION CONDITIONS; ORGANOSILANES; SEM AND TEM; SEMIHYDROGENATION; UNSUPPORTED GOLD;

ADDITIVES; CATALYST ACTIVITY; GOLD; HYDROGEN; OLEFINS; ORGANIC COMPOUNDS; PARAFFINS;

ACETYLENE;

ALKENE; ALKYNE; AMINE; GOLD NANOPARTICLE; HYDROGEN; NANOPOROUS GOLD; PYRIDINE; SILANE DERIVATIVE; SOLVENT; UNCLASSIFIED DRUG; WATER;

ARTICLE; ATOM; CATALYSIS; CHEMICAL STRUCTURE; CONTROLLED STUDY; HYDROGENATION; NANOCATALYST; REACTION OPTIMIZATION; REDUCTION; SCANNING ELECTRON MICROSCOPY; TRANSMISSION ELECTRON MICROSCOPY;

ALKENES; ALKYNES; AMINES; GOLD; HYDROGENATION; METAL NANOPARTICLES; MOLECULAR STRUCTURE; PARTICLE SIZE; POROSITY; SURFACE PROPERTIES;

EID: 84867795821     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja3087592     Document Type: Article

References (62)

1. Zielasek, V.; Jürgens, B.; Schulz, C.; Biener, J.; Biener, M. M.; Hamza, A. V.; Bäumer, M. Angew. Chem., Int. Ed. 2006, 45, 8241
2. Xu, C.; Su, J.; Xu, X.; Liu, P.; Zhao, H.; Tian, F.; Ding, Y. J. Am. Chem. Soc. 2007, 129, 42
3. Xu, C.; Xu, X.; Su, J.; Ding, Y. J. Catal. 2007, 252, 243
4. Wittstock, A.; Neumann, B.; Schaefer, A.; Dumbuya, K.; Kübel, C.; Biener, M. M.; Zielasek, V.; Steinrück, H. P.; Gottfried, J. M.; Biener, J.; Hamza, A.; Bäumer, M. J. Phys. Chem. C 2009, 113, 5593
5. Wang, L. C.; Jin, H. J.; Widmann, D.; Weissmuller, J.; Behm, R. J. J. Catal. 2011, 278, 219
6. Wittstock, A.; Zielasek, V.; Biener, J.; Friend, C. M.; Bäumer, M. Science 2010, 327, 319
7. Asao, N.; Hatakeyama, N.; Menggenbateer; Minato, T.; Ito, E.; Hara, M.; Kim, Y.; Yamamoto, Y.; Chen, M.; Zhang, W.; Inoue, A. Chem. Commun. 2012, 48, 4540
8. Yin, H.; Zhou, C.; Xu, C.; Liu, P.; Xu, X.; Ding, Y. J. Phys. Chem. C 2008, 112, 9673
9. Kosuda, K. M.; Wittstock, A.; Friend, C. M.; Bäumer, M. Angew. Chem., Int. Ed. 2012, 51, 1698
10. Zhang, J.; Liu, P.; Ma, H.; Ding, Y. J. Phys. Chem. C 2007, 111, 10382
11. Yu, C.; Jia, F.; Ai, Z.; Zhang, L. Chem. Mater. 2007, 19, 6065
12. Zeis, R.; Lei, T.; Sieradzki, K.; Snyder, J.; Erlebacher, J. J. Catal. 2008, 253, 132
13. Forty, A. J. Nature 1979, 282, 597
14. Erlebacher, J.; Aziz, M. J.; Karma, A.; Dimitrov., N.; Sieradzki, K. Nature 2001, 410, 450
15. Hashmi, A. S. K.; Hutchings Angew. Chem., Int. Ed. 2006, 45, 7896
16. Pina, C. D.; Falletta, E.; Prati, L.; Rossi, M. Chem. Soc. Rev. 2008, 37, 2077
17. Corma, A.; Garcia, H. Chem. Soc. Rev. 2008, 37, 2096
18. Matsumoto, T.; Ueno, M.; Wang, N.; Kobayashi, S. Chem.-Asian J. 2008, 3, 196
19. Corma, A.; Leyva-Pérez, A.; Sabater, M. J. Chem. Rev. 2011, 111, 1657
20. Fujita, T.; Guan, P.; McKenna, K.; Lang, X.; Hirata, A.; Zhang, L.; Tokunaga, T.; Arai, S.; Yamamoto, Y.; Tanaka, N.; Ishikawa, Y.; Asao, N.; Yamamoto, Y.; Erlebacher, J.; Chen, M. W. Nat. Mater. 2012, 11, 775-780
21. Bond, G. C.; Louis, C.; Thompson, D. T. Catalysis by Gold; Imperial College Press: London, 2006, Chapter 9, p 244.
22. McEwan, L.; Julius, M.; Roberts, S.; Fletcher, J. C. Q. Gold Bull. 2010, 43, 298
23. Fujitani, T.; Nakamura, I.; Akita, T.; Okumura, M.; Haruta, M. Angew. Chem., Int. Ed. 2009, 48, 9515
24. Hauwert, P.; Maestri, G.; Sprengers, J. W.; Catellani, M.; Elsevier, C. J. Angew. Chem., Int. Ed. 2008, 47, 3223
25. La Pierre, H. S.; Arnold, J.; Toste, F. D. Angew. Chem., Int. Ed. 2011, 50, 3900
26. Gianetti, T. L.; Tomson, N. C.; Arnold, J.; Bergman, R. G. J. Am. Chem. Soc. 2011, 133, 14904
27. Shen, R.; Chen, T.; Zhao, Y.; Qiu, Y.; Zhou, Y.; Yin, S.; Wang, X.; Goto, M.; Han, L.-B. J. Am. Chem. Soc. 2011, 133, 17037
28. Lindlar, H. Helv. Chim. Acta 1952, 35, 446
29. Savoia, D.; Tagliavini, E.; Trombini, C.; Umani-Ronchi, A. J. Org. Chem. 1981, 46, 5340
30. Brunet, J. J.; Caubere, P. J. Org. Chem. 1984, 49, 4058
31. Gruttadauria, M.; Noto, R.; Deganello, G.; Liotta, L. F. Tetrahedron Lett. 1999, 40, 2857
32. Gruttadauria, M.; Liotta, L. F.; Noto, R.; Deganello, G. Tetrahedron Lett. 2001, 42, 2015
33. Alonso, F.; Osante, I.; Yus, M. Adv. Synth. Catal. 2006, 348, 305
34. Hori, J.; Murata, K.; Sugai, T.; Shinohara, H.; Noyori, R.; Arai, N.; Kurono, N.; Ohkuma, T. Adv. Synth. Catal. 2009, 351, 3143
35. Venkatesan, R.; Prechtl, M. H. G.; Scholten, J. D.; Pezzi, R. P.; Machado, G.; Dupont, J. J. Mater. Chem. 2011, 21, 3030
36. Wu, J.; Wang, K.; Li, Y.; Yu, P. Adv. Mater. Res. 2011, 233-235, 2109
37. Takahashi, Y.; Hashimoto, N.; Hara, T.; Shimazu, S.; Mitsudome, T.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Chem. Lett. 2011, 40, 405
38. Segura, Y.; López, N.; Pérez-Ramíez, J. J. Catal. 2007, 247, 383
39. Jia, J.; Haraki, K.; Kondo, J. N.; Domen, K.; Tamaru, K. J. Phys. Chem. B 2000, 104, 11153
40. Choudhary, T. V.; Sivadinarayana, C.; Datye, A. K.; Kumar, D.; Goodman, D. W. Catal. Lett. 2003, 86, 1
41. Azizi, Y.; Petit, C.; Pitchon, V. J. Catal. 2008, 256, 338-344
42. Nikolaev, S. A.; Smirnov, V. V. Catal. Today 2009, 147S, S336
43. Asao, N.; Ishikawa, Y.; Hatakeyama, N.; Menggenbateer; Yamamoto, Y.; Chen, M.; Zhang, W.; Inoue, A. Angew. Chem., Int. Ed. 2010, 49, 10093
44. Tanaka, S.; Kaneko, T.; Asao, N.; Yamamoto, Y.; Chen, M.; Zhang, W.; Inoue, A. Chem. Commun. 2011, 47, 5985
45. Kaneko, T.; Tanaka, S.; Asao, N.; Yamamoto, Y.; Chen, M.; Zhang, W.; Inoue, A. Adv. Synth. Catal. 2011, 353, 2927
46. Jin, T.; Yan, M.; Menggenbateer; Minato, T.; Bao, M.; Yamamoto, Y. Adv. Synth. Catal. 2011, 353, 3095
47. Asao, N.; Meggenbateer; Seya, Y.; Yamamoto, Y.; Chen, M.; Zhang, W.; Inoue, A. Synlett 2012, 23, 66
48. Asao, N.; Jin, T.; Tanaka, S.; Yamamoto, Y. Pure Appl. Chem. 2012, 84, 1771
49. Jin, T.; Yan, M.; Yamamoto, Y. ChemCatChem 2012, 4, 1217
50. Mohr, C.; Hofmeister, H.; Radnik, J.; Claus, P. J. Am. Chem. Soc. 2003, 125, 1905
51. Corma, A.; Boronat, M.; Gonzalez, S.; Illas, F. Chem. Commun. 2007, 3371
52. Zhu, Y.; Qian, H.; Drake, B. A.; Jin, R. Angew. Chem., Int. Ed. 2010, 49, 1295
53. Schreiner, S.; Yu, J. Y.; Vaska, L. Inorg. Chim. Acta 1988, 147, 139
54. Sharma, H. K.; Panel, K. H. Angew. Chem., Int. Ed. 2009, 48, 7052
55. Itazaki, M.; Ueda, K.; Nakazawa, H. Angew. Chem., Int. Ed. 2009, 48, 3313
56. Brunet, J. J.; Caubere, P. J. Org. Chem. 1984, 49, 4058
57. Heathcock, C. H.; Ratcliffe, R. J. Am. Chem. Soc. 1971, 93, 1746
58. Hönig, H.; Seufer-Wasserthal, P.; Weber, H. Tetrahedron 1990, 46, 3841
59. Bridier, B.; López, N.; Pérez-Ramírez, J. Dalton Trans. 2010, 39, 8412
60. Noujima, A.; Mitsudome, T.; Mizugaki, T.; Jitsukawa, K.; Kaneda, K. Angew. Chem., Int. Ed. 2011, 50, 2986
61. Fang, M.; Machalaba, N.; Sánchez-Delgado, R. A. Dalton Trans. 2011, 40, 10621
62. Goethals, M.; Zeegers-Huyskens, T. Spectrosc. Lett. 1995, 28, 1125