Abstract
Silica-supported catalyst exhibiting sulfonic groups was proved effective in the Baeyer–Villiger oxidation to the lactones from the corresponding cyclic ketones in high yields with clean hydrogen peroxide in acetonitrile at mild conditions. Moreover, the catalyst was easily recovered and could be reused at least four times without significant decline in catalytic activity.
Similar content being viewed by others
References
G.C. Krow, Org. React. 43, 251–298 (1993)
R. Bernini, A. Coratti, G. Fabrizi, A. Goggiamani, Tetrahedron Lett. 44, 8991–8994 (2003)
M. Renz, B. Meunier, Eur. J. Org. Chem. 4, 737–750 (1999)
A. Chrobok, S. Baj, W. Pudło, A. Jarzebski, Appl. Catal. A Gen. 366, 22–28 (2009)
Z. Lei, L. Wei, R. Wang, G. Ma, Catal. Commun. 9, 2467–2469 (2008)
S. Baj, A. Chrobok, Synth. Commun. 38, 2385–2391 (2008)
K.B. Szpakolski, K. Latham, C.J. Rix, J.M. White, Inorg. Chim. Acta 376, 628–633 (2011)
T. Hara, M. Hatakeyama, A. Kim, N. Ichikuni, S. Shimazu, Green Chem. 14, 771–777 (2012)
A.J. Kotlewska, F. Rantwijk, R.A. Sheldon, I.W.C.E. Arends, Green Chem. 13, 2154–2160 (2011)
G. Strukul, A. Varagnolo, F. Pinna, J. Mol. Catal. A Chem. 117, 413–423 (1997)
C. Palazzi, F. Pinna, G. Strukul, J. Mol. Catal. A Chem. 151, 245–252 (2000)
R. Bernini, E. Mincione, M. Cortese, R. Saladino, G. Gualandi, M.C. Belfiore, Tetrahedron Lett. 44, 4823–4825 (2003)
J. Fischer, W.F. Holderich, Appl. Catal. A Gen. 180, 435–443 (1999)
A. Corma, M.T. Navarro, M. Renz, J. Catal. 219, 242–246 (2003)
W.F. Holderich, J. Fischer, G. Schindler, P. Arntz, German Patent DE 19745442 (1999)
B. Notari, Adv. Catal. 41, 253–334 (1996)
K. Kaneda, S. Ueno, T. Imanaka, J. Mol. Catal. A Chem. 102, 135–138 (1995)
Y. Liu, C.L. Chen, N.P. Xu, Chin. J. Catal. 25, 801–804 (2004)
R.P. Unnikrishnan, S.D. Endalkachew, J. Mol. Catal. A Chem. 191, 93–100 (2003)
N. Alonso-Fagúndez, V. Laserna, A.C. Alba-Rubio, M. Mengibarb, A. Herasb, R. Mariscala, M.L. Granados. Catal. Today http://dx.doi.org/10.1016/j.cattod.2014.01.041
T. Kawabata, Y. Ohishi, S. Itsuki, N. Fujisaki, T. Shishido, K. Takaki, Q. Zhang, Y. Wang, K. Takehira, J. Mol. Catal. A 236, 99–106 (2005)
P.K. Jal, S. Patel, B.K. Mishra, Talanta 62, 1005–1028 (2004)
Y.C. Ko, B.D. Ratner, A.S. Hoffman, J. Colloid Interface Sci 86, 25–37 (1982)
C.H. Chiang, H. Ishida, J.L. Koenig, J. Colloid Interface Sci. 74, 396–404 (1980)
H. Ishida, J.L. Koenig, Polym. Eng. Sci. 18, 128–145 (1978)
H. Ishida, J.L. Koenig, J. Colloid Interface Sci. 64, 555–564 (1977)
J. Lin, H. Chen, Y. Ji, Y. Zhang, Colloids Surf. A Physicochem. Eng. Asp. 411, 111–121 (2012)
G. Corro, F. Bañuelos, E. Vidal, S. Cebada, Fuel 115, 625–628 (2014)
B.I. Lee, U. Paik, J. Mater. Sci. 27, 5692–5700 (1992)
M. Kamada, H. Kominami, Y. Kera, J. Colloid Interface Sci. 182, 297–300 (1996)
H. Li, R. Wang, H. Hu, W. Liu, Appl. Surf. Sci. 255, 1894–1900 (2008)
S.J. Park, K.S. Cho, J. Colloid Interface Sci. 267, 86–91 (2003)
B. Wei, Q. Chang, C. Bao, L. Dai, G. Zhang, F. Wu, Colloids Surf. A Physicochem. Eng. Asp. 434, 276–280 (2013)
R. Maggi, G. Martra, C.G. Piscopo, G. Alberto, G. Sartori, J. Catal. 294, 19–28 (2012)
J. Chen, M. Asano, Y. Maekawa, M. Yoshida, J. Membr. Sci. 296, 77–82 (2007)
Acknowledgments
This Project is funded by the Priority Academic Program Development of Jiangsu Higher Education Institutions (PAPD).
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Xing, W., Ma, Q., Xu, J. et al. Baeyer–Villiger oxidation of cyclic ketones with hydrogen peroxide catalyzed by silica–VTMO–OSO3H. J Porous Mater 22, 487–492 (2015). https://doi.org/10.1007/s10934-015-9918-8
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10934-015-9918-8