Chinese Journal of Organic Chemistry >
Asymmetric Transfer Hydrogenation of Acetophenone Promoted by Chitosan Ester Ruthenium Complex
Received date: 2014-06-18
Revised date: 2014-07-30
Online published: 2014-08-26
Supported by
Project supported by the Natural Science Foundation of Hebei Province (No. B2011202087).
The catalytic properties of the catalyst generated in situ from the reaction of Ru(II) compounds with chitosan based ligands were evaluated in the asymmetric transfer hydrogenation of acetophenone using isopropanol or sodium formate as hydrogen source. The effects of reaction time, temperature and the dosage of THF on the performance of the catalyst were evaluated. The O-stearoyl chitosan (SCS) is in the form of micelles with the average size of 213 nm in i-PrOH/THF solution. Using i-PrOH as hydrogen source, the ee value of 1-phenylethanol is up to 62.9%. The dosage of THF strongly affected the catalytic activity. The catalytic activity (TOF) is up to 30.4 h-1 at the volume ratio of i-PrOH to THF being 1:1. The TOF increased with the increase of the temperature. At 100 ℃, the TOF is up to 48.5 h-1. While using HCOONa as the hydrogen source, the TOF and ee values of 1-phenylethanol are 29.4 h-1 and 53.0%, respectively.
Liu Bing , Zhou Hongyong , Li Yunqing , Wang Jiaxi . Asymmetric Transfer Hydrogenation of Acetophenone Promoted by Chitosan Ester Ruthenium Complex[J]. Chinese Journal of Organic Chemistry, 2014 , 34(12) : 2554 -2558 . DOI: 10.6023/cjoc201406025
[1] Li, X.-N.; Zhou, H.-Y.; Feng, L.; Duan, K.; Wang J.-X. Appl. Organomet. Chem. 2012, 26, 168.
[2] Malacea, R.; Poli, R.; Manoury, E. Coord. Chem. Rev. 2010, 254, 729.
[3] Song, S-S.; Zhou, H.-Y.; Li, X.-N.; Wang, L.-H.; Li, Y.-Q.; Wang, J.-X. Chin. J. Org. Chem. 2014, 34, 706 (in Chinese). (宋莎莎, 周宏勇, 李小娜, 王丽华, 李云庆, 王家喜, 有机化学, 2014, 34, 706.)
[4] Fu, Q.; Zhang, L.; Yi, T.; Zou M.-J.; Wang, X.-Y.; Fu, H.-Y.; Li, R.-X.; Chen, H. Inorg. Chem. Commun. 2013, 38, 28.
[5] Li, X.-N.; Zhang, P.-L.; Duan, K.; Wang, J.-X. Chin. J. Org. Chem. 2012, 32, 19 (in Chinese). (李小娜, 张鹏亮, 段凯, 王家喜, 有机化学, 2012, 32, 19.)
[6] Thakur, K. G.; Ganapathy, D.; Sekar, G. Chem. Commun. 2011, 47, 5076.
[7] Zhao, D.-Q.; He, M.; Zhang, Y.-H.; Huang, M.-Y.; Jiang, Y.-Y. Polym. Adv. Technol. 2003, 14(3～5), 287.
[8] Yi, Y.; Wang, Y.-T.; Wan, L.-L.; Zhang, X.-Y.; Ma, S.-L. J. Wuhan Technol. (Mater. Sci. Ed.) 2007, 22(1), 156.
[9] Yin, M.-Y.; Yuan, G.-L.; Wu, Y.-Q.; Huang, M.-Y.; Jiang, Y.-Y. J. Mol. Catal. A: Chem. 1999, 147, 93.
[10] Zhou, D.-Q.; Zhou, D.-J.; Cui, X.-H.; Wang, F.-M.; Huang, M.-Y.; Jiang, Y.-Y. Polym. Adv. Technol. 2004, 15, 350.
[11] Wei, W.-L.; Hao, S.-J.; Zhou, J.; Huang, M. Y.; Jiang, Y.-Y. Polym. Adv. Technol. 2004, 15, 287.
[12] Babin, M.; Clément, R.; Gagnon, J.; Fontaine, F. G. New J. Chem. 2012, 36, 1548.
[13] Badawy, M. E. I.; Rabea, E. I.; Rogge, T. M.; Stevens, C. V.; Smagghe, G.; Steurbaut, W.; Höfte, M. Biomacromolecules 2004, 5, 589.
[14] Sun, Y.-X.; Guo, Y.; Lu, G.-Z.; Wu, X.-H.; Guo, Y.-L.; Wang, Y.-S.; Liu, X.-H.; Zhang, Z.-G. J. Mol. Catal. (China) 2004, 18(6), 456 (in Chinese). (孙延喜, 郭耘, 卢冠忠, 吴小华, 郭杨龙, 王筠松, 刘晓晖, 张志刚, 分子催化, 2004, 18(6), 456.)
[15] Ding, K.-L.; Fan, Q.-H. Asymmetric Catalysis: New Concepts and Methods, Chemical Industry Press, Beijin, 2009 (in Chinese). (丁奎岭, 范青华, 不对称催化新概念与新方法, 化学工业出版社, 北京, 2009.)
[16] Luo, Y.-R.; Yu, S.-Q.; Zhang, D.-Z.; Yao, T.-Y.; Gao, P.-L. Univ. Chem. 2010, 25(3), 35 (in Chinese). (罗渝然, 俞书勤, 张祖德, 姚天扬, 高盘良, 大学化学, 2010, 25(3), 35.)
[17] Fehring, V.; Kadyrov, R.; Ludwig, M.; Holz, J.; Haage, K.; Selke, R. J. Organomet. Chem. 2001, 621, 120.
[18] Li, J.-H.; Tang, Y.-F.; Wang, Q.-W.; Li, X.-F.; Cun, L.-F.; Zhang, X.-M.; Zhu, J.; Li, L.-C.; Deng, J.-G. J. Am. Chem. Soc. 2012, 134, 18522.
[19] Watts, C.-C.; Thoniyot, P.; Cappuccio, F.; Verhagen, J.; Gallagher, B.; Singgraram, B. Tetrahedron: Asymmetry 2006, 17, 1301.
[20] Sun, Y.-X.; Guo, Y.; Wu, X.-H.; Meng, X.-L.; Lu, G.-Z.; Guo, Y.-L. Chin. J. Appl. Chem. 2006, 23(1), 42 (in Chinese). (孙延喜, 郭耘, 吴小华, 孟宪乐, 卢冠忠, 应用化学, 2006, 23(1), 42.)
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