11
28. Yoo, W.-J.; Yuan, H.; Miyamura, H.; Kobayashi, S. Adv. Synth.
The yield was determined by GC analysis with reference to an
internal standard (anisole).
ACCEPTED MANUSCRIPT
Catal. 2011, 353, 3085–3089.
29. Miyamura, H.; Maehata, K.; Kobayashi, S. Chem. Commun. 2010,
46, 8052–8054.
30. Miyamura, H.; Shiramizu, M.; Matsubara, R.; Kobayashi, S.
Angew. Chem., Int. Ed. 2008, 47, 8093–8095.
31. Nishio, R.; Sugiura, M.; Kobayashi, S. Org. Biomol. Chem. 2006,
4, 992–995.
32. Okamoto, K.; Akiyama, R.; Yoshida, H.; Yoshida, T.; Kobayashi,
S. J. Am. Chem. Soc. 2005, 127, 2125–2135.
33. Soulé, J.-F.; Miyamura, H.; Kobayashi, S. J. Am. Chem. Soc. 2013,
135, 10602–10605.
4.5.8. Aerobic oxidation of 1-phenyl-2-
(trimethylsilyloxy)propan-1-one catalyzed by PI-Au
4l:
1-Phenyl-2-(trimethylsilyloxy)propan-1-one (5f) (55.5 mg,
0.25 mmol), PI-Au 4l (0.240 mmol/g, 1 mol%), toluene (1.0 mL)
and water (1.0 mL) were combined in a round-bottom flask. The
mixture was stirred for 15 h under O2 at 80 °C. The catalyst was
collected by filtration and washed with ethyl acetate, using a
Kiriyamarohto® funnel. The aqueous layer was extracted with
ethyl acetate (20 30 ml). The combined organic layers were
dried over sodium sulfate. The yield was determined by GC
analysis with reference to an internal standard (anisole).
34. Yasukawa, T.; Miyamura, H.; Kobayashi, S. J. Am. Chem. Soc.
2012, 134, 16963–16966.
35. Conte, M.; Miyamura, H.; Kobayashi, S.; Chechik, V. J. Am. Chem.
Soc. 2009, 131, 7189–7196.
36. Conte, M.; Miyamura, H.; Kobayashi, S.; Chechik, V. Chem.
Commun. 2010, 46, 145–147.
37. Lucchesi, C.; Inasaki, T.; Miyamura, H.; Matsubara, R.; Kobayashi,
S. Adv. Synth. Catal. 2008, 350, 1996–2000.
Acknowledgements
38. Miyamura, H.; Kobayashi, S. Chem. Lett. 2012, 41, 976–978.
39. Miyamura, H.; Matsubara, R.; Miyazaki, Y.; Kobayashi, S. Angew.
Chem., Int. Ed. 2007, 46, 4151–4154.
40. Miyamura, H.; Morita, M.; Inasaki, T.; Kobayashi, S. Bull. Chem.
Soc. Jpn. 2011, 84, 588–599.
41. Miyamura, H.; Shiramizu, M.; Matsubara, R.; Kobayashi, S. Chem.
Lett. 2008, 37, 360–361.
42. Miyamura, H.; Yasukawa, T.; Kobayashi, S. Green Chem. 2010,
12, 776–778.
This work was partially supported by a Grant-in-Aid for
Scientific Research from JSPS, MEXT (Japan), JST, NEDO,
METI and The University of Tokyo. T. Y. thanks JSPS for the
Research Fellowship for Young Scientists. We thank Mr.
Noriaki Kuramitsu (The University of Tokyo) for STEM and
EDS analyses.
43. Soulé, J.-F.; Miyamura, H.; Kobayashi, S. J. Am. Chem. Soc. 2011,
133, 18550–18553.
References
44. Soulé, J.-F.; Miyamura, H.; Kobayashi, S. Asian J. Org. Chem.
2012, 1, 319–321.
45. Soulé, J.-F.; Miyamura, H.; Kobayashi, S. Chem. Asian J. 2013, 8,
2614–2626.
46. Wang, N.; Matsumoto, T.; Ueno, M.; Miyamura, H.; Kobayashi, S.
Angew. Chem., Int. Ed. 2009, 48, 4744–4746.
47. Yasukawa, T.; Miyamura, H.; Kobayashi, S. Chem. Asian J. 2011,
6, 621–627.
48. Kaizuka, K.; Lee, K.-Y.; Miyamura, H.; Kobayashi, S. J. Flow
Chem. 2012, 2, 1–4.
1. Haruta, M.; Kobayashi, T.; Sano, H.; Yamada, N. Chem. Lett. 1987,
2, 405–408.
2. Haruta, M.; Yamada, N.; Kobayashi, T.; Iijima, S. J. Catal. 1989,
115, 301–309.
3. Arcadi, A. Chem. Rev. 2008, 108, 3266–3325.
4. Corma, A.; García, H. Chem. Soc. Rev. 2008, 37, 2096–2126.
5. Della Pina, C.; Falletta, E.; Prati, L.; Rossi, M. Chem. Soc. Rev.
2008, 37, 2077–2095.
6. Li, Z. G.; Brouwer, C.; He, C. Chem. Rev. 2008, 108, 3239–3265.
7. Corma, A.; Leyva-Pérez, A.; Sabater, M. J. Chem. Rev. 2011, 111,
1657–1712.
49. Kaizuka, K.; Miyamura, H.; Kobayashi, S. J. Am. Chem. Soc. 2010,
132, 15096–15098.
50. Miyamura, H.; Matsubara, R.; Kobayashi, S. Chem. Commun.
2008, 2031–2033.
51. Soulé, J.-F.; Miyamura, H.; Kobayashi, S. Chem. Commun. 2013,
49, 355–357.
52. Yoo, W.-J.; Miyamura, H.; Kobayashi, S. J. Am. Chem. Soc. 2011,
133, 3095–3103.
53. Miyamura, H.; Choo, G. C. Y.; Yasukawa, T.; Yoo, W.-J.;
Kobayashi, S. Chem. Commun. 2013, 49, 9917–9919.
54. Miyamura, H.; Kobayashi, S. Acc. Chem. Res. 2014, 47, 1054.
55. Nakazawa, M.; Somorjai, G. A. Appl. Surf. Sci. 1993, 68, 517–537.
56. Kumar, A.; Mandal, S.; Mathew, S. P.; Selvakannan, P. R.;
Mandale, A. B.; Chaudhari, R. V.; Sastry, M. Langmuir 2002, 18,
6478–6483.
8. Ishida, T.; Haruta, M. Angew. Chem., Int. Ed. 2007, 46, 7154–7156.
9. Tsukuda, T.; Tsunoyama, H.; Sakurai, H. Chem. Asian J. 2011, 6,
736–748.
10. Dimitratos, N.; Lopez-Sanchez, J. A.; Hutchings, G. J. Chem. Sci.
2012, 3, 20–44.
11. Aschwanden, L.; Mallat, T.; Maciejewski, M.; Krumeich, F.;
Baiker, A. ChemCatChem 2010, 2, 666–673.
12. So, M.-H.; Liu, Y.; Ho, C.-M.; Che, C.-M. Chem. Asian J. 2009, 4,
1551–1561.
13. Grirrane, A.; Corma, A.; Garcia, H. J. Catal. 2009, 264, 138–144.
14. Zhu, B.; Angelici, R. J. Chem. Commun. 2007, 2157–2159.
15. Carrettin, S.; Guzman, J.; Corma, A. Angew. Chem., Int. Ed. 2005,
44, 2242–2245.
57. Ramanath, G.; D'Arcy-Gall, J.; Maddanimath, T.; Ellis, A. V.;
Ganesan, P. G.; Goswami, R.; Kumar, A.; Vijayamohanan, K.
Langmuir 2004, 20, 5583–5587.
16. Chaicharoenwimolkul, L.; Munmai, A.; Chairam, S.; Tewasekson,
U.; Sapudom, S.; Lakliang, Y.; Somsook, E. Tetrahedron Lett.
2008, 49, 7299–7302.
58. Maddanimath, T.; Kumar, A.; D'Arcy-Gall, J.; Ganesan, P. G.;
Vijayamohanan, K.; Ramanath, G. Chem. Commun. 2005, 1435–
1437.
59. Kobayashi, J.; Mori, Y.; Okamoto, K.; Akiyama, R.; Ueno, M.;
Kitamori, T.; Kobayashi, S. Science 2004, 304, 1305–1308.
60. Kobayashi, S.; Miyamura, H.; Akiyama, R.; Ishida, T. J. Am.
Chem. Soc. 2005, 127, 9251–9254.
61. Tsunoyama, H.; Sakurai, H.; Negishi, Y.; Tsukuda, T. J. Am. Chem.
Soc. 2005, 127, 9374–9375.
62. Clark, R. D.; Heathcock, C. H. Tetrahedron Lett. 1974, 15, 2027–
2030.
17. Tsunoyama, H.; Sakurai, H.; Ichikuni, N.; Negishi, Y.; Tsukuda, T.
Langmuir 2004, 20, 11293–11296.
18. Willis, N. G.; Guzman, J. Appl. Catal. A: General 2008, 339, 68–
75.
19. Gao, L.; Nishikata, T.; Kojima, K.; Chikama, K.; Nagashima, H.
Chem. Asian J. 2013, 8, 3152–3163.
20. Akiyama, R.; Kobayashi, S. Chem. Rev. 2009, 109, 594–642.
21. Kobayashi, S.; Miyamura, H. Chem. Rec. 2010, 10, 271–290.
22. Kobayashi, S.; Miyamura, H. Aldrichimica Acta 2013, 46, 3–19.
23. Kobayashi, S.; Nagayama, S. J. Am. Chem. Soc. 1998, 120, 2985–
2986.
63. Rubottom, G. M.; Vazquez, M. A.; Pelegrina, D. R. Tetrahedron
Lett. 1974, 15, 4319–4322.
24. Akiyama, R.; Kobayashi, S. J. Am. Chem. Soc. 2003, 125, 3412–
3413.
64. Hassner, A.; Reuss, R. H.; Pinnick, H. W. J. Org. Chem. 1975, 40,
3427–3429.
25. Yuan, H.; Yoo, W.-J.; Miyamura, H.; Kobayashi, S. Adv. Synth.
Catal. 2012, 354, 2899–2904.
65. Rubottom, G. M.; Gruber, J. M. J. Org. Chem. 1978, 43, 1599–
1602.
26. Yuan, H.; Yoo, W.-J.; Miyamura, H.; Kobayashi, S. J. Am. Chem.
Soc. 2012, 134, 13970–13973.
66. Rubottom, G. M.; Gruber, J. M.; Mong, G. M. J. Org. Chem. 1976,
41, 1673–1674.
27. Yoo, W.-J.; Yuan, H.; Miyamura, H.; Kobayashi, S. Can. J. Chem.
2012, 90, 306–313.