journal article·2016-02

Exploring porous nanosilica-TEMPO as heterogeneous aerobic oxidation catalyst: the influence of supported gold clusters

Ahmed J. Shakir, Mihaela Florea, Daniela C. Culita, Gabriela Ionita, Corneliu Ghica, Cristina Stavarache, Anamaria Hanganu, Petre Ionita

Journal of Porous Materials· Volume 23· Issue 1
Publisher page

Abstract

TEMPO stable free radical has been supported on porous silica nanoparticles in different ways and the resulted materials have been tested as heterogeneous oxidation catalyst of three benzylic alcohols using air as final oxidant and nitrosonium tetrafluoroborate as cocatalyst. Good to excellent yields were obtained. The catalytic system consists in fact in two coupled cycles, NO/NO2 and TEMPO+/TEMPO, able to convert under mild conditions (room temperature, air, metal and halogen free condition) alcohols into aldehydes or ketones. Under these conditions, supported TEMPO on silica nanoparticles containing gold clusters lowers the efficiency of the catalyst.
Source: openaire · Quality: candidate unverified · Source record ↗

Research context

OpenAlex topics: Oxidative Organic Chemistry Reactions · Catalytic Processes in Materials Science · Catalysis and Oxidation Reactions

SciVX discovery tags are terminology-based. OpenAlex topics are source-provided classifications.

References (35)

Show source-provided references
1. R. Ciriminna, M. Pagliano, Org. Process Res. Dev. 14, 245 (2010)10.1021/op900059x ↗
2. R.A. Sheldon, J.K. Kochi, Metal Catalyzed Oxidation of Organic Compounds (Academic Press, New York, 1981)
3. J.H. Clark, Acc. Chem. Res. 35, 791 (2002)10.1021/ar010072a ↗
4. J.E. Backvall, Modern Oxidation Methods (Wiley, Weinheim, 2004)10.1002/3527603689 ↗
5. G. Tojo, M. Fernandez, Oxidation of Alcohols to Aldehydes and Ketones (Springer, Berlin, 2006)
6. D.B. Dess, J.C. Martin, J. Org. Chem. 48, 4155 (1983)10.1021/jo00170a070 ↗
7. T. Fey, S. Bachmann, K. Albert, C. Bolm, J. Org. Chem. 66, 8154 (2001)10.1021/jo010535q ↗
8. B.A. Steinhoff, I.A. Guzei, S.S. Stahl, J. Am. Chem. Soc. 126, 11268 (2004)10.1021/ja049962m ↗
9. B.A. Steinhoff, S.S. Stahl, J. Am. Chem. Soc. 128, 4348 (2006)10.1021/ja057914b ↗
10. D. Lenoir, Angew. Chem. Int. Ed. 45, 3206 (2006)10.1002/anie.200502702 ↗
11. M. Holan, U. Jahn, Org. Lett. 16, 58 (2014)10.1021/ol403016p ↗
12. B. Karimi, A. Biglari, J.H. Clark, V. Budarin, Angew. Chem. Int. Ed. 46, 7210 (2007)10.1002/anie.200701918 ↗
13. P. Ionita, RSC Adv. 3, 21218 (2013)10.1039/c3ra44863k ↗
14. M. Kuroboshi, K. Goto, H. Tanaka, Synthesis 6, 0903 (2009)
15. T. Luts, E. Iglesia, A. Katz, J. Mater. Chem. 21, 982 (2011)10.1039/C0JM02826F ↗
16. M. Shibuya, Y. Osada, Y. Sasano, M. Tomizawa, Y. Iwabuchi, J. Am. Chem. Soc. 133, 6497 (2011)10.1021/ja110940c ↗
17. B.L. Ryland, S.S. Stahl, Angew. Chem. Int. Ed. 53, 8824 (2014)10.1002/anie.201403110 ↗
18. G. Yang, W. Wang, W. Zhu, C. An, X. Gao, M. Song, Synlett 3, 437 (2010)10.1055/s-0029-1219202 ↗
19. S. Wertz, A. Studer, Green Chem. 15, 3116 (2013)10.1039/c3gc41459k ↗
20. Y. Yan, X. Tong, K. Wang, X. Bai, Catal. Commun. 43, 112 (2014)10.1016/j.catcom.2013.09.022 ↗
21. M. Haruta, N. Yamada, T. Kobayashi, S. Iijima, J. Catal. 15, 301 (1989)10.1016/0021-9517(89)90034-1 ↗
22. H. Tsunoyama, H. Sakurai, T. Tsukuda, Chem. Phys. Lett. 429, 528 (2006)10.1016/j.cplett.2006.08.066 ↗
23. Y. Li, Y. Gao, C. Yang, Chem. Commun. 51, 7721 (2015)10.1039/C5CC01053E ↗
24. H. Tsunoyama, H. Sakurai, Y. Negishi, T. Tsukuda, J. Am. Chem. Soc. 127, 9374 (2005)10.1021/ja052161e ↗
25. T.A. Graf, T.K. Anderson, N.B. Bowden, Adv. Synth. Catal. 353, 1033 (2011)10.1002/adsc.201000859 ↗
26. L. Wang, J. Li, W. Dai, Y. Lv, Y. Zhang, S. Gao, Green Chem. 16, 2164 (2014)10.1039/c3gc42075b ↗
27. T. Ishida, M. Nagaoka, T. Akita, M. Haruta, Chem. Eur. J. 14, 8456 (2008)10.1002/chem.200800980 ↗
28. R.V. Jagadeesh, H. Junge, M.M. Pohl, J. Radnik, A. Bruckner, M. Beller, J. Am. Chem. Soc. 135, 10776 (2013)10.1021/ja403615c ↗
29. P. Ionita, F. Spafiu, C. Ghica, J. Mater. Sci. 43, 6571 (2008)10.1007/s10853-008-2987-1 ↗
30. H. Zhang, L. Fu, Synthetic Commun. 44, 610 (2014)10.1080/00397911.2013.827207 ↗
31. A. Macado, M.H. Casimiro, L.M. Ferreira, J.E. Castanheiro, A.M. Ramos, I.M. Fonseca, J. Vital, Microporous Mesoporous Mater. 203, 63 (2015)10.1016/j.micromeso.2014.10.019 ↗
32. Q. Cao, L.M. Dornan, L. Rogan, N.L. Hughes, M.J. Muldoon, Chem. Commun. 50, 4524 (2014)10.1039/C3CC47081D ↗
33. K.V. Narayana, B.D. Raju, S.K. Masthan, V.V. Rao, P.K. Rao, R. Subrahmanian, A. Martin, Catal. Commun. 5, 487 (2004)10.1016/j.catcom.2004.05.012 ↗
34. M. Shibuya, S. Nagasawa, Y. Osada, Y. Iwabuchi, J. Org. Chem. 79, 10256 (2014)10.1021/jo501862k ↗
35. R.A. Sheldon, Catal. Today 247, 4 (2015)10.1016/j.cattod.2014.08.024 ↗