Aquacatalytic aerobic oxidation of benzylic alcohols with a self-supported bipyridyl-palladium complex

Chemistry Letters

Volumn 38, Issue 9, 2009, Pages 902-903

  Osako, Takao ^a   Uozumi, Yasuhiro ^a,b  

^a INSTITUTE FOR MOLECULAR SCIENCE   (Japan)

^b RIKEN   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 76949089509     PISSN: 03667022     EISSN: 13480715     Source Type: Journal    
DOI: 10.1246/cl.2009.902     Document Type: Article

References (36)

1. R. A. Sheldon, J. K. Kochi, Metal-Catalyzed Oxidations of Organic Compounds, Academic Press, New York, 1981.
2. M. Hudlucky, Oxidations in Organic Chemistry, ACS Monograph Series, American Chemical Society, Washington, DC, 1990.
3. T. Mallat, A. Baiker, Chem. Rev. 2004, 104, 3037.
4. T. Matsumoto, M. Ueno, N. Wang, S. Kobayashi, Chem. Asian J. 2008, 3, 196.
5. For examples of aerobic oxidation with heterogeneous catalysts in organic solvents, see: a) K. Yamaguchi, K. Mori, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 2000, 122, 7144.
6. N. Kakiuchi, Y. Maeda, T. Nishimura, S. Uemura, J. Org. Chem. 2001, 66, 6620.
7. K. Yamaguchi, N. Mizuno, Angew. Chem., Int. Ed. 2002, 41, 4538.
8. Y.-C. Son, V. D. Makwana, A. R. Howell, S. L. Suib, Angew. Chem., Int. Ed. 2001, 40, 4280.
9. K. Mori, T. Hara, T. Mizugaki, K. Ebitani, K. Kaneda, J. Am. Chem. Soc. 2004, 126, 10657.
10. H. Miyamura, R. Matsubara, Y. Miyazaki, S. Kobayashi, Angew. Chem., Int. Ed. 2007, 46, 4151.
11. For examples of aerobic oxidation with heterogeneous catalysts in water, see: a) Y. Uozumi, R. Nakao, Angew. Chem., Int. Ed., 2003, 42, 194.
12. Y. M. A. Yamada, T. Arakawa, H. Hocke, Y. Uozumi, Angew. Chem., Int. Ed. 2007, 46, 704.
13. A. Abad, P. Concepción, A. Corma, H. García, Angew. Chem., Int. Ed. 2005, 44, 4066. See also reference 3e.
14. For examples of aerobic oxidation with heterogeneous catalysts under solvent-free conditions, see: a) D. I. Enache, J. K. Edwards, P. Landon, B. Solsona-Espriu, A. F. Carley, A. A. Herzing, M. Watanabe, C. J. Kiely, D. W. Knight, G. J. Hutchings, Science 2006, 311, 362.
15. N. Zheng, G. D. Stucky, Chem. Commun. 2007, 3862. See also references 3c, 3e, 3f and 4c.
16. G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Science 2000, 287, 1636.
17. G.-J. ten Brink, I. W. C. E. Arends, R. A. Sheldon, Adv. Synth. Catal. 2002, 344, 355.
18. G.-J. ten Brink, I. W. C. E. Arends, M. Hoogenraad, G. Verspui, R. A. Sheldon, Adv. Synth. Catal. 2003, 345, 497.
19. I. W. C. E. Arends, G.-J. ten Brink, R. A. Sheldon, J. Mol. Catal. A: Chem. 2006, 251, 246.
20. B. P. Buffin, N. L. Belitz, S. L. Verbeke, J. Mol. Catal. A: Chem. 2008, 284, 149.
21. Z. Wang, G. Chen, K. Ding, Chem. Rev. 2009, 109, 322.
22. L.-X. Dai, Angew. Chem., Int. Ed. 2004, 43, 5726.
23. P. M. Forster, A. K. Cheetham, Top. Catal. 2003, 24, 79.
24. Y. M. A. Yamada, Y. Maeda, Y. Uozumi, Org. Lett. 2006, 8, 4259.
25. B. Xing, M.-F. Choi, B. Xu, Chem. - Eur. J. 2002, 8, 5028.
26. C. N. Kato, M. Ono, T. Hino, T. Ohmura, W. Mori, Catal. Commun. 2006, 7, 673.
27. See Supporting Information for experimental details. Supporting Information is available electronically in the CSJ-Journal Web site, http://www.csj.jp/journals/chem-lett/index.html.
28. 2BPy-Cu Would Show 2D Or 3D Network Structure. See The Related Copper Complexes: a) L. Deakin, A. M. Arif, J. S. Miller, Inorg. Chem. 1999, 38, 5072.
29. H.-D. Bian, J.-Y. Xu, W. Gu, S.-P. Yan, D.-Z. Liao, Z.-H. Jiang, P. Cheng, Inorg. Chem. Commun. 2003, 6, 573.
30. W. Mori, T. Sato, C. N. Kato, T. Takei, T. Ohmura, Chem. Rec. 2005, 5, 336.
31. 3) had to be generated from the catalyst in situ.
32. The yield depended on the polarity of used solvents. Thus, the reaction was promoted in more polar solvents.
33. II-promoted oxidative reactions, see: a) R. M. Trend, Y. K. Ramtohul, B. M. Stolz, J. Am. Chem. Soc. 2005, 127, 17778.
34. Y. Uozumi, K. Kato, T. Hayashi, J. Am. Chem. Soc. 1997, 119, 5063.
35. Y. Uozumi, K. Kato, T. Hayashi, J. Org. Chem. 1998, 63, 5071.
36. Average yields of three separate recycling runs. TEM analysis of the catalyst after the 1st reaction showed no formation of palladium particles.