IBX Oxidation of Benzenedimethanols in the Presence of Cucurbit[8]uril
Corresponding Author
Hang Cong
Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, Guizhou 550025, China
Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi1, Saga 840-8502, Japan
Hang Cong, Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, Guizhou 550025, China
Takehiko Yamato, Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi1, Saga 840-8502, Japan
Search for more papers by this authorQiuju Chen
Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, Guizhou 550025, China
Search for more papers by this authorQingxia Geng
Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, Guizhou 550025, China
Search for more papers by this authorZhu Tao
Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, Guizhou 550025, China
Search for more papers by this authorCorresponding Author
Takehiko Yamato
Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi1, Saga 840-8502, Japan
Hang Cong, Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, Guizhou 550025, China
Takehiko Yamato, Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi1, Saga 840-8502, Japan
Search for more papers by this authorCorresponding Author
Hang Cong
Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, Guizhou 550025, China
Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi1, Saga 840-8502, Japan
Hang Cong, Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, Guizhou 550025, China
Takehiko Yamato, Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi1, Saga 840-8502, Japan
Search for more papers by this authorQiuju Chen
Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, Guizhou 550025, China
Search for more papers by this authorQingxia Geng
Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, Guizhou 550025, China
Search for more papers by this authorZhu Tao
Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, Guizhou 550025, China
Search for more papers by this authorCorresponding Author
Takehiko Yamato
Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi1, Saga 840-8502, Japan
Hang Cong, Key Laboratory of Macrocyclic and Supramolecular Chemistry of Guizhou Province, Guizhou University, Guiyang, Guizhou 550025, China
Takehiko Yamato, Department of Applied Chemistry, Faculty of Science and Engineering, Saga University, Honjo-machi1, Saga 840-8502, Japan
Search for more papers by this authorAbstract
The cucurbit[8]uril (Q[8]) mediated oxidation of benzenedimethanols with o-iodoxybenzoic acid (IBX) in aqueous solution has been investigated, and the results reveal the supramolecular catalysis depends on the electronic and geometric structure of substrate. In the cases of o-benzenedimethanol (1a) and m-benzenedimethanol (1b), the IBX oxidation could be obviously enhanced by the addition of Q[8] at different extent. There is no observation of the catalytic activity of Q[8] when p-benzenedimethanol (1c) is subjected to the IBX oxidation. The addition amount of Q[8] is discussed herein, and the addition of more than 10% mol catalyst cannot improve the oxidation much more. The investigation of host-guest interactions by isothermal titration calorimetry implies the supramolecular catalysis is related to the formation of complexes between benzenedimethanols and cucurbit[8]uril.
REFERENCES
- 1 Masson, E.; Ling, X.; Joseph, R.; Kyeremeh-Mensah, L.; Lu, X.. RSC Adv., 2012, 2, 1213.
- 2 Pemberton, B. C.; Raghunathan, R.; Volla, S.; Sivaguru, J.. Chem. Eur. J., 2012, 18, 12178.
- 3 Cong, H.; Tao, Z.; Xue, S.-F.; Zhu, Q.-J.. Curr. Org. Chem., 2011, 15, 86.
- 4 Assaf, K. I.; Nau, W. M.. Chem. Soc. Rev., 2015, 44, 394.
- 5 Mock, W. L.; Irra, T. A.; Wepsiec, J. P.; Adhya, M., J. Org. Chem., 1989, 54, 5302.
- 6 Carlqvista, P.; Maseras, F.. Chem. Commun., 2007, 748.
- 7 Jon, S. Y.; Ko, Y. H.; Park, S. H.; Kim, H.-J.; Kim, K.. Chem. Commun., 2001, 1938.
- 8 Yang, C.; Mori, T.; Origane, Y.; Ko, Y. H.; Selvapalam, N.; Kim, K.; Inoue, Y.. J. Am. Chem. Soc., 2008, 130, 8574.
- 9 Yang, C.; Ke, C.; Liang, W.; Fukuhara, G.; Mori, T.; Liu, Y.; Inoue, Y.. J. Am. Chem. Soc., 2011, 133, 13786.
- 10 Cong, H.; Wang, Q.-S.; Zhang, J.-X.; Tao, Z.; Xue, S.-F.. Chin. J. Org. Chem., 2012, 32, 1093.
- 11 de Lima, S. M.; Gómez, J. A.; Barros, V. P.; Vertuan, G. D.; Assis, M. D.; Graeff, C. F. D.; Demets, G. J.-F.. Polyhedron, 2010, 29, 3008.
- 12 Lu, X. Y.; Masson, E.. Org. Lett., 2010, 12, 2310.
- 13 Koner, A. L.; Márquez, C.; Dickman, M. H.; Nau, W. M.. Angew. Chem., Int. Ed., 2011, 50, 545.
- 14 Zhao, G.; Wang, Z.; Wang, R.; Li, J.; Zou, D.; Wu, Y.. Tetrahedron Lett., 2014, 55, 5319.
- 15 Cong, H.; Zhao, F.-F.; Zhang, J.-X.; Zeng, X.; Tao, Z.; Xue, S.-F.; Zhu, Q.-J.. Catal. Commun., 2009, 11, 167.
- 16 Wang, Y.-H.; Cong, H.; Zhao, F.-F.; Xue, S.-F.; Tao, Z.; Wei, G.. Catal. Commun., 2011, 12, 1127.
- 17 Cong, H.; Li, Z.-J.; Wang, Y.-H.; Tao, Z.; Yamato, T.; Xue, S.-F.; Wei, G.. J. Mol. Catal. A: Chem., 2013, 374–375, 32.
- 18 Cong, H.; Yamato, T.; Tao, Z.. New J. Chem., 2013, 37, 3778.
- 19 Satam, V.; Harad, A.; Rajule, R.; Pati, H.. Tetrahedron, 2010, 66, 7659.
- 20 Duschek, A.; Kirsch, S. F.. Angew. Chem., Int. Ed., 2011, 50, 1524.
- 21 Thottumkara, A. P.; Vinod, T. K.. Tetrahedron Lett., 2002, 43, 569.
- 22 Moorthy, J. N.; Singhal, N.; Venkatakrishnan, P.. Tetrahedron Lett., 2004, 45, 5419.
- 23 Bernini, R.; Mincione, E.; Barontini, M.; Crisante, F.. J. Agric. Food Chem., 2008, 56, 8897.
- 24 Magdziak, D.; Rodriguez, A. A.; Van De Water, R. W.; Pettus, T. R. R.. Org. Lett., 2002, 4, 3339.
- 25 Wu, A.; Duan, Y.; Xu, D.; Penning, T. M.; Harvey, R. G.. Tetrahedron, 2010, 66, 2111.
- 26 Nicolaou, K. C.; Mathison, C. J. N.; Montagnon, T.. J. Am. Chem. Soc., 2004, 126, 5192.
- 27 Murthy, S. N.; Nageswar, Y. V. D.. Tetrahedron Lett., 2011, 52, 4481.
- 28 Zhang, G.-L.; Xu, Z.-Q.; Xue, S.-F.; Zhu, Q.-J.; Tao, Z.. Chin. J. Inorg. Chem., 2003, 19, 655.
- 29 Frigerio, M.; Santagostino, M.; Sputore, S.. J. Org. Chem., 1999, 64, 4537.