Aerobic oxidations catalyzed by colloidal nanogold

Chemistry - An Asian Journal

Volumn 6, Issue 3, 2011, Pages 736-748

  Tsukuda, Tatsuya ^a   Tsunoyama, Hironori ^a   Sakurai, Hidehiro ^b  

^a HOKKAIDO UNIVERSITY   (Japan)

^b INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

Author keywords

colloids; gold; homogeneous catalysis; Lewis acids; nanoparticles

Indexed keywords

AEROBIC OXIDATIONS; BENZYLIC; CATALYTIC REACTIONS; COMPREHENSIVE STUDIES; ELECTRON TRANSFER; GOLD CLUSTERS; GOLD NANOCLUSTER; HOMOCOUPLING REACTIONS; HOMOGENEOUS CATALYSIS; HOMOGENEOUS CATALYST; HYDROALKOXYLATION; HYDROAMINATIONS; LEWIS ACIDIC; LEWIS ACIDIC CENTERS; LEWIS ACIDS; LIQUID MEDIA; MECHANISTIC STUDIES; N-VINYL-2-PYRROLIDONE; NANO-GOLD; OXIDATION REACTIONS; POLY(N-VINYL-2-PYRROLIDONE); RECENT PROGRESS; SUPEROXIDES;

CATALYSIS; CATALYSTS; COLLOID CHEMISTRY; COLLOIDS; GOLD; HYDROXYLATION; KETONES; NANOPARTICLES; OLEFINS; OXIDATION; OXYGEN; REACTION KINETICS;

GOLD COMPOUNDS;

EID: 79951999740     PISSN: 18614728     EISSN: 1861471X     Source Type: Journal    
DOI: 10.1002/asia.201000611     Document Type: Review

References (123)

1. M. Haruta, N. Yamada, T. Kobayashi, S. Iijima, J. Catal. 1989, 115, 301-309
2. M. Haruta, T. Kobayashi, H. Sano, N. Yamada, Chem. Lett. 1987, 405-408.
3. S. S. Stahl, Angew. Chem. 2004, 116, 3480-3501
4. Angew. Chem. Int. Ed. 2004, 43, 3400-3420
5. T. Mallat, A. Baiker, Chem. Rev. 2004, 104, 3037-3058.
6. M. Haruta, Chem. Rec. 2003, 3, 75-87
7. A. S. K. Hashmi, G. J. Hutchings, Angew. Chem. 2006, 118, 8064-8105
8. Angew. Chem. Int. Ed. 2006, 45, 7896-7936
9. A. S. K. Hashmi, Chem. Rev. 2007, 107, 3180-3211
10. A. Corma, H. Garcia, Chem. Soc. Rev. 2008, 37, 2096-2126
11. C. Della Pina, E. Falletta, L. Prati, M. Rossi, Chem. Soc. Rev. 2008, 37, 2077-2096.
12. M. Comotti, C. Della Pina, R. Matarrese, M. Rossi, Angew. Chem. 2004, 116, 5936-5939
13. Angew. Chem. Int. Ed. 2004, 43, 5812-5815.
14. L. D. Socaciu, J. Hagen, T. M. Bernhardt, L. Wöste, U. Heiz, H. Häkkinen, U. Landman, J. Am. Chem. Soc. 2003, 125, 10437-10445.
15. Y. D. Kim, M. Fischer, G. Ganteför, Chem. Phys. Lett. 2003, 377, 170-176.
16. T. Yonezawa, N. Toshima, in Advanced Functional Molecules and Polymers (Ed.:, H. S. Nalwa,), OPA, Amsterdam, 2001, p. 65.
17. R. L. Whetten, J. T. Khoury, M. M. Alvarez, S. Murthy, I. Vezmar, Z. L. Wang, P. W. Stephens, C. L. Cleveland, W. D. Luedtke, U. Landman, Adv. Mater. 1996, 8, 428-433
18. G. Schmid, Chem. Soc. Rev. 2008, 37, 1909-1930
19. J. F. Parker, C. A. Fields-Zinna, R. W. Murray, Acc. Chem. Res. 2010, 43, 1289-1296
20. R. Jin, Nanoscale 2010, 2, 343-362.
21. T. Teranishi, M. Hosoe, M. Miyake, Adv. Mater. 1997, 9, 65-67
22. T. Teranishi, M. Miyake, Chem. Mater. 1998, 10, 594-600
23. N. Toshima, in Nanoscale Materials (Eds.:, L. M. Liz-Marzán, P. V. Kamat,), Kluwer Academic Publishers, Norwell, MA, 2003, pp. 79-96
24. R. Narayanan, M. A. El-Sayed, J. Phys. Chem. B 2005, 109, 12663-12676
25. Y. Zhang, M. E. Grass, J. N. Kuhn, F. Tao, S. E. Habas, W. Huang, P. Yang, G. A. Somorjai, J. Am. Chem. Soc. 2008, 130, 5868-5869.
26. A. Biffis, S. Cunial, P. Spontoni, L. Prati, J. Catal. 2007, 251, 1-6.
27. A. Biffis, L. Minati, J. Catal. 2005, 236, 405-409.
28. C. Burato, P. Centomo, G. Pace, M. Favaro, L. Prati, B. Corain, J. Mol. Catal. A 2005, 238, 26-34.
29. S. Kanaoka, N. Yagi, Y. Fukuyama, S. Aoshima, H. Tsunoyama, T. Tsukuda, H. Sakurai, J. Am. Chem. Soc. 2007, 129, 12060-12061.
30. Y. Wang, R. Yan, J. Zhang, W. Zhang, J. Mol. Catal. A 2010, 317, 81-88.
31. H. Tsunoyama, H. Sakurai, N. Ichikuni, Y. Negishi, T. Tsukuda, Langmuir 2004, 20, 11293-11296.
32. H. Tsunoyama, N. Ichikuni, T. Tsukuda, Langmuir 2008, 24, 11327-11330.
33. H. Tsunoyama, T. Tsukuda, J. Am. Chem. Soc. 2009, 131, 18216-18217.
34. H. Tsunoyama, H. Sakurai, Y. Negishi, T. Tsukuda, J. Am. Chem. Soc. 2005, 127, 9374-9375
35. H. Tsunoyama, H. Sakurai, T. Tsukuda, Chem. Phys. Lett. 2006, 429, 528-532
36. H. Tsunoyama, N. Ichikuni, H. Sakurai, T. Tsukuda, J. Am. Chem. Soc. 2009, 131, 7086-7093.
37. H. Tsunoyama, T. Tsukuda, H. Sakurai, Chem. Lett. 2007, 36, 212-213.
38. Y. Uozumi, R. Nakao, Angew. Chem. 2003, 115, 204-207
39. Angew. Chem. Int. Ed. 2003, 42, 194-197.
40. Y. M. A. Yamada, T. Arakawa, H. Hocke, Y. Uozumi, Angew. Chem. 2007, 119, 718-720
41. Angew. Chem. Int. Ed. 2007, 46, 704-706
42. T. Wang, H. Shou, Y. Kou, H. Liu, Green Chem. 2009, 11, 562-568.
43. P. G. N. Mertens, I. F. J. Vankelecom, P. A. Jacobs, D. E. de Vos, Gold Bull. 2005, 38, 157-162.
44. X. Wang, H. Kawanami, N. M. Islam, M. Chattergee, T. Yokoyama, Y. Ikushima, Chem. Commun. 2008, 4442-4444.
45. A. Villa, D. Wang, D. S. Su, L. Prati, ChemCatChem 2009, 1, 510-514.
46. H. Miyamura, R. Matsubara, Y. Miyazaki, S. Kobayashi, Angew. Chem. 2007, 119, 4229-4232
47. Angew. Chem. Int. Ed. 2007, 46, 4151-4154.
48. H. Miyamura, T. Yasukawa, S. Kobayashi, Green Chem. 2010, 12, 776-778.
49. J. Han, Y. Liu, R. Guo, Adv. Funct. Mater. 2009, 19, 1112-1117.
50. J. Han, Y. Liu, L. Li, R. Guo, Langmuir 2009, 25, 11054-11060.
51. T. Ishida, S. Okamoto, R. Makiyama, M. Haruta, Appl. Catal. A 2009, 353, 243-248.
52. A. Villa, C. E. Chan-Thaw, L. Prati, Appl. Catal. B 2010, 96, 541-547.
53. A. Bongiorno, U. Landman, Phys. Rev. Lett. 2005, 95, 106102.
54. A. Fielicke, G. von Helden, G. Meijer, B. Simard, D. M. Rayner, J. Phys. Chem. B 2005, 109, 23935-23940.
55. W. T. Wallace, R. L. Whetten, J. Am. Chem. Soc. 2002, 124, 7499-7505.
56. T. Ishida, M. Nagaoka, T. Akita, M. Haruta, Chem. Eur. J. 2008, 14, 8456-8460.
57. M. Okumura, Y. Kitagawa, T. Kawakami, M. Haruta, Chem. Phys. Lett. 2008, 459, 133-136.
58. N. K. Chaki, H. Tsunoyama, Y. Negishi, H. Sakurai, T. Tsukuda, J. Phys. Chem. C 2007, 111, 4885-4888.
59. M. Conte, H. Miyamura, S. Kobayashi, V. Chechik, J. Am. Chem. Soc. 2009, 131, 7189-7196
60. M. Conte, H. Miyamura, S. Kobayashi, V. Chechik, Chem. Commun. 2010, 46, 145-147.
61. J. Guzman, S. Carrettin, A. Corma, J. Am. Chem. Soc. 2005, 127, 3286-3287.
62. S. Biella, L. Prati, M. Rossi, J. Catal. 2002, 206, 242-247.
63. T. Ishida, H. Watanabe, T. Bebeko, T. Akita, M. Haruta, Appl. Catal. A 2010, 377, 42-46.
64. C. Gunanathan, Y. Ben-David, D. Milstein, Science 2007, 317, 790-792
65. L. U. Nordstrøm, H. Vogt, R. Madsen, J. Am. Chem. Soc. 2008, 130, 17672-17673
66. W.-J. Yoo, C.-J. Li, J. Am. Chem. Soc. 2006, 128, 13064-13065
67. S. Seo, T. J. Marks, Org. Lett. 2008, 10, 317-319.
68. P. Preedasuriyachai, H. Kitahara, W. Chavasiri, H. Sakurai, Chem. Lett. 2010, 39, 1174-1176.
69. T. Ishida, M. Haruta, ChemSusChem 2009, 2, 538-541.
70. B. Xu, L. Zhou, R. J. Madix, C. M. Friend, Angew. Chem. 2010, 122, 404-408
71. Angew. Chem. Int. Ed. 2010, 49, 394-398.
72. K. Shimizu, K. Ohshima, A. Satsuma, Chem. Eur. J. 2009, 15, 9977-9980
73. L. Zhou, C. G. Freyschlag, B. Xu, C. M. Friend, R. J. Madix, Chem. Commun. 2010, 46, 704-706.
74. Y. Zhu, H. Qian, M. Zhu, R. Jin, Adv. Mater. 2010, 22, 1915-1920.
75. H. Sakurai, I. Kamiya, H. Kitahara, H. Tsunoyama, T. Tsukuda, Synlett 2009, 245-248.
76. K. A. Smith, E. M. Campi, W. R. Jackson, S. Marcuccio, C. G. M. Naeslund, G. B. Deacon, Synlett 1997, 131-132
77. H. Yoshida, Y. Yamaryo, J. Ohshita, A. Kunai, Tetrahedron Lett. 2003, 44, 1541-1544
78. S. Punna, D. D. Díaz, M. G. Finn, Synlett 2004, 2351-2354
79. Y. Yamamoto, R. Suzuki, K. Hattori, H. Nishiyama, Synlett 2006, 1027-1030
80. K. Cheng, B. Xin, Y. Zhang, J. Mol. Catal. A 2007, 273, 240-243
81. Y. Yamamoto, Synlett 2007, 1913-1916.
82. S. Carrettin, J. Guzman, A. Corma, Angew. Chem. 2005, 117, 2282-2285
83. Angew. Chem. Int. Ed. 2005, 44, 2242-2245.
84. C. González-Arellano, A. Corma, M. Iglesias, F. Sánchez, Chem. Commun. 2005, 1990-1992.
85. N. G. Willis, J. Guzman, Appl. Catal. A 2008, 339, 68-75
86. L. Chaicharoenwimolkul, A. Munmai, S. Chairam, U. Tewasekson, S. Sapudom, Y. Lakliang, E. Somsook, Tetrahedron Lett. 2008, 49, 7299-7302.
87. H. Sakurai, H. Tsunoyama, T. Tsukuda, J. Organomet. Chem. 2007, 692, 368-374.
88. H. Sakurai, H. Tsunoyama, T. Tsukuda, Trans. Mater. Res. Soc. Jpn. 2006, 31, 521-524.
89. I. Kamiya, H. Tsunoyama, T. Tsukuda, H. Sakurai, Chem. Lett. 2007, 36, 646-647.
90. J. Muzart, Tetrahedron 2005, 61, 5955-6008
91. T. Hosokawa, S. Murahashi, Acc. Chem. Res. 1990, 23, 49-54.
92. S. Inoki, T. Mukaiyama, Chem. Lett. 1990, 67-70
93. Y. M. A. Yamada, H. Guo, Y. Uozumi, Org. Lett. 2007, 9, 1501-1504, and references therein.
94. H. Kitahara, I. Kamiya, H. Sakurai, Chem. Lett. 2009, 38, 908-909.
95. T. E. Müller, M. Beller, Chem. Rev. 1998, 98, 675-704
96. T. E. Müller, K. C. Hultzsch, M. Yus, F. Foubelo, M. Tada, Chem. Rev. 2008, 108, 3795-3892.
97. H. Kitahara, H. Sakurai, J. Organomet. Chem. 2011, 696, 442-449
98. H. Sakurai, I. Kamiya, H. Kitahara, Pure Appl. Chem. 2010, 82, 2005-2016.
99. H. Kitahara, H. Sakurai, Chem. Lett. 2010, 39, 46-48.
100. S. Hong, T. J. Marks, Acc. Chem. Res. 2004, 37, 673-686.
101. S. Majumder, A. L. Odom, Organometallics 2008, 27, 1174-1177
102. J. A. Bexrud, J. D. Beard, D. C. Leitch, L. L. Schafer, Org. Lett. 2005, 7, 1959-1962
103. J. Y. Kim, T. Livinghouse, Org. Lett. 2005, 7, 4391-4393.
104. J. Seayad, A. Tillack, C. G. Hartung, M. Beller, Adv. Synth. Catal. 2002, 344, 795-813
105. C. Quinet, P. Jourdain, C. Hermans, A. Ates, I. Lucas, I. E. Marko, Tetrahedron 2008, 64, 1077-1087.
106. Z. Liu, J. F. Hartwig, J. Am. Chem. Soc. 2008, 130, 1570-1571
107. H. Ohmiya, T. Moriya, M. Sawamura, Org. Lett. 2009, 11, 2145-2147
108. K. D. Hesp, M. Stradiotto, Org. Lett. 2009, 11, 1449-1452
109. C. F. Bender, R. A. Widenhoefer, Chem. Commun. 2006, 4143-4144
110. C. F. Bender, R. A. Widenhoefer, Chem. Commun. 2008, 2741-2743
111. E. B. Bauer, G. T. S. Andavan, T. K. Hollis, R. J. Rubio, J. Cho, G. R. Kuchenbeiser, T. R. Helgert, C. S. Letko, F. S. Tham, Org. Lett. 2008, 10, 1175-1178
112. A. Minatti, K. Müniz, Chem. Soc. Rev. 2007, 36, 1142-1152.
113. C. F. Bender, R. A. Widenhoefer, J. Am. Chem. Soc. 2005, 127, 1070-1071
114. C. F. Bender, W. B. Hudson, R. A. Widenhoefer, Organometallics 2008, 27, 2356-2358
115. X. Wang, R. A. Widenhoefer, Organometallics 2004, 23, 1649-1651
116. C. Liu, C. F. Bender, X. Han, R. A. Widenhoefer, Chem. Commun. 2007, 3607-3618
117. A. M. Johns, M. Utsunomiya, C. D. Incarvito, J. F. Hartwig, J. Am. Chem. Soc. 2006, 128, 1828-1839
118. K. Li, P. N. Horton, M. B. Hursthouse, K. K. Hii, J. Organomet. Chem. 2003, 665, 250-257.
119. C. Xu, L. Sun, L. J. Kepley, R. M. Crooks, Anal. Chem. 1993, 65, 2102-2107
120. D. V. Leff, L. Brandt, J. R. Heath, Langmuir 1996, 12, 4723-4730
121. A. Kumar, S. Mandal, P. R. Selvakannan, R. Pasricha, A. B. Mandale, M. Sastry, Langmuir 2003, 19, 6277-6282
122. K. S. Mayya, F. Caruso, Langmuir 2003, 19, 6987-6993.
123. R. Narayanan, C. Tabor, M. A. El-Sayed, Top. Catal. 2008, 48, 60-74.