Ring-Opening of Oxiranes using Taeniolite-Supported Tris(β-Diketonato)Zirconium

Yessi Permana, Nobuyuki Ichikuni, Shogo Shimazu

Abstract


A series of tris(β-diketonato)zirconium(IV) complexes was immobilized into a synthetic clay structure of Taeniolite by an ion-exchange method to generate organic/inorganic hybrid compounds. The hybrid compound served as a good catalyst for ring-opening reactions of methyl, ethyl, and dimethyl oxiranes with various alcohols to generate primary alkoxy alcohols in appreciable selectivity. This method describes a technique to immobilize cationic zirconium complexes without losing selectivity.

Full Text:

PDF

References


Takeuchi, H., Kitajima, K., Yamamoto, Y. & Mizuno, K., The Use of Proton-Exchanged X-Type Zeolite in Catalysing Ring-Opening Reactions of 2-Substituted Epoxides with Nucleophiles and Its Effect on Regioselectivity, J. Chem. Soc., Perk. T. 2, 2, pp. 199-203, 1993.

Barluenga, J., Vázquez-Villa, H., Ballesteros, A. & González, J.M., Copper(II) Tetrafluoroborate Catalyzed Ring-Opening Reaction of Epoxides with Alcohols at Room Temperature, Org. Lett., 4, pp. 2817-2819, 2002.

Permana, Y., Shimazu, S., Ichikuni, N. & Uematsu, T., Selective Synthesis of Primary Methoxypropanol Using Clay Supported Tris(2,4- pentanedionato)zirconium(IV), J. Mol. Catal. A-Chem., 221, pp. 141-144, 2004.

Chakraborti, A.K., Kondaska, A. & Rudrawar, S., Scope and Limitations of Montmorillonite K 10 Catalysed Opening of Epoxide Rings by Amines, Tetrahedron, 60, pp. 9085-9091, 2004.

Dioos, B.M.L., Geurts, W.A. & Jacobs, P.A., Coordination of CrIII(Salen) on Functionalised Silica for Asymmetric Ring-Opening Reactions of Epoxides, Catal. Lett., 97, pp. 125-129, 2004.

Chakraborti, A.K., Rudrawar, S. & Kondaskar, A., An Efficient Synthesis of 2-Amino Alcohols by Silica Gel Catalysed Opening of Epoxide Rings by Amines, Org. Biomol. Chem., 2, pp. 1277-1280, 2004.

Permana, Y., Shimazu, S., Ichikuni, N. & Uematsu, T., Studies on Tris(Β- Diketonato)Zirconium(IV); Syntheses, Characterization and Cata-lytic Activity for Ring-Opening of Oxirane, Catal. Commun., 6, pp. 426-430 2005.

Shimazu, S., Hong Zou, Hara, T. & Ichikuni, N., Regioselective Ring Opening Reactions of Oxiranes with Acrylic Acid by Clay Supported Zirconium β-Diketonate Catalysts, J. Ion Exchange. A., 18, pp. 584-589, 2007.

Robinson, M.W.C., Buckle, R., Mabbett, I., Grant, G.M. & Graham, A.E., Mesoporous Aluminosilicate Promoted Alcoholysis of Epoxides, Tetrahedron Lett., 48, pp. 4723-4725, 2007.

Liu, Y.-H., Liu, Q.-S. & Zhang, Z.-H., Amberlyst-15 As A New and Reusable Catalyst for Regioselective Ring-Opening Reactions of Epoxides to Β-Alkoxy Alcohols, J. Mol. Catal. A-Chem., 296, pp. 42-46, 2008.

Mancilla, G., Femenía-Ríos, M., Macías-Sánchez, A.J. & Collado, I.G., Sn(OTf)2 Catalysed Regioselective Styrene Oxide Ring-Opening with Aromatic Amines, Tetrahedron, 64, pp. 11732-11737, 2008.

Guo, X.-F., Kim, Y.-S. & Kim, G.-J., Chiral (Salen) Cobalt Complexes Encapsulated in Mesoporous MFI as an Enantioselective Catalyst for Asymmetric Ring-Opening of Terminal Epoxides, Top. Catal., 52, pp. 153-160, 2008.

Torborg, C., Hughes, D.D., Buckle, R., Robinson, M.W.C., Bagley, M.C., Graham, A.E., Rapid Ring‐Opening Reactions of Epoxides using Microwave Irradiation, Synthetic Commun., 38, pp. 205-211, 2008.

Robinson, M.W.C., Davies, A.M., Mabbett, I., Apperley D.C., Taylor, S.H., Graham, A.E., Synthesis and Catalytic Activity of Nanoporous Aluminosilicate Materials, J. Mol. Catal. A-Chem., 314, pp. 10-14, 2009.

Robinson, M.W.C., Davies, A.M., Richard, B., Mabbett, I., Taylor, S.H., Graham, A.E., Epoxide Ring-Opening and Meinwald Rearrangement Reactions of Epoxides Catalyzed by Mesoporous Aluminosilicates, Org. Biomol. Chem., 7, pp. 2559-2564, 2009.

Li, Y., Hao, H.-D. & Wu, Y., Facile Ring-Opening of Oxiranes by H2O2 Catalyzed by Phosphomolybdic Acid, Org. Lett., 11, pp. 2691-2694, 2009.

Jafarpour, M., Rezaeifard, A. & Aliabadi, M., An Environmentally Benign Catalytic Method for Efficient and Selective Nucleophilic Ring Opening of Oxiranes by Zirconium Tetrakis(dodecyl Sulfate), Helv. Chim. Acta, 93, pp. 405-413, 2010.

Selvin, R., Selva Roselin, L., Praveen Kumar, K. & Arul, S., Nanocrystalline Zeolite Beta: An Efficient Catalyst for The Regioselective Alcoholysis of Epichlorohydrin, Sci. Adv. Mater., 2, pp. 190-194, 2010.

Zaccheria, F., Santoro, F., Psaro, R. & Ravasio, N., Cuo/Sio2: A Simple And Efficient Solid Acid Catalyst For Epoxide Ring Opening, Green Chem., 13, pp. 545-548, 2011.

Das, S. & Asefa, T., Epoxide Ring-Opening Reactions with Mesoporous Silica-Supported Fe(III) Catalysts, ACS Catal., 1, pp. 502-510, 2011.

Capes, A.S., Crossman, A.T., Webster, L.A., Ferguson, M. A.J. & Gilbert, I.H., Investigation of Copper(II) Tetrafluoroborate Catalysed Epoxide Opening, Tetrahedron Lett., 52, pp. 7091-7094, 2011.

Izquierdo, J., Rodríguez, S. & González, F.V., Regioselective Ring Opening and Isomerization Reactions of 3,4-Epoxyesters Catalyzed by Boron Trifluoride, Org. Lett., 13, pp. 3856-3859, 2011.

Venkatasubbaiah, K., Zhu, X., Kays, E., Hardcastle, K.I. & Jones, C.W.,Co(III)-Porphyrin-Mediated Highly Regioselective Ring-Opening of Terminal Epoxides with Alcohols and Phenols, ACS Catal., 1, pp. 489-492, 2011.

Hu, X., Gao, B., Chu, Y., Li, W., Liu, X., Lin, L. & Feng, X., Enantioselective Synthesis of β-Pyrazole-Substituted Alcohols through an Asymmetric Ring-Opening Reaction of Meso-Epoxides. Chem.–Eur. J., 18, pp. 3473-3477, 2012.

Kahandal, S.S., Kale, S.R., Disale, S.T. & Jayaram, R.V., Sulphated Yttria–Zirconia as A Regioselective Catalyst System for The Alcoholysis of Epoxides, Catal. Sci. Technol., 2, pp. 1493-1499, 2012.

Newman, A.C.D., Chemistry of Clay and Clay Minerals, Harlow, Longman, pp. 81-83, 1987.

Suzuki, N., Yamamoto, D., Anaguchi, N., Tsuchiya, H., Aoki, K. & Kanzaki, Y., The Ion-Exchange Property of Some Layered Inorganic Materials with Potassium Ion, Rubidium Ion and Cesium Ion, and Selective Cesium Ion-Exchange of Synthetic Mica, Bull. Chem. Soc. Jpn, 73, pp. 2599-2603, 2000.

Suzuki, N., Itoh, M., Igarashi, M. & Kanzaki, Y., Solid NMR Study of the Ion-Exchange Properties on -Titanium Phosphate with Alkali Metal Ions, J. Ion Exchange, 14, pp. 169-172, 2003.




DOI: http://dx.doi.org/10.5614%2Fitbj.sci.2012.44.3.6

Refbacks

  • There are currently no refbacks.


View my Stats

Creative Commons License
This work is licensed under a Creative Commons Attribution-NoDerivatives 4.0 International License.

 

ITB Journal Publisher, LPPM ITB, Center for Research and Community Services (CRCS) Building, 6th & 7th Floor, Jalan Ganesha 10, Bandung 40132, Indonesia, Tel. +62-22-86010080, Fax.: +62-22-86010051; E-mail: jmfs@lppm.itb.ac.id