Asymmetric Transfer Hydrogenation of Acetophenone Promoted by Chitosan Ester Ruthenium Complex

doi:10.6023/cjoc201406025

Chin. J. Org. Chem. ›› 2014, Vol. 34 ›› Issue (12): 2554-2558.DOI: 10.6023/cjoc201406025 Previous Articles Next Articles

Notes

壳聚糖酯钌络合物催化苯乙酮的不对称氢转移反应

刘兵, 周宏勇, 李云庆, 王家喜

河北工业大学化工学院天津 300130

收稿日期:2014-06-18 修回日期:2014-07-30 发布日期:2014-08-26
通讯作者: 王家喜 E-mail:wangjiaxi@hebut.edu.cn
基金资助:
河北省自然科学基金(No.B2011202087)资助项目.

Asymmetric Transfer Hydrogenation of Acetophenone Promoted by Chitosan Ester Ruthenium Complex

Liu Bing, Zhou Hongyong, Li Yunqing, Wang Jiaxi

School of Chemical Engineering, Hebei University of Technology, Tianjin 300130

Received:2014-06-18 Revised:2014-07-30 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.

Key words: chitosan, O-stearoyl chitosan, asymmetric transfer hydrogenation, acetophenone

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Liu Bing, Zhou Hongyong, Li Yunqing, Wang Jiaxi. Asymmetric Transfer Hydrogenation of Acetophenone Promoted by Chitosan Ester Ruthenium Complex[J]. Chin. J. Org. Chem., 2014, 34(12): 2554-2558.

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壳聚糖酯钌络合物催化苯乙酮的不对称氢转移反应

Asymmetric Transfer Hydrogenation of Acetophenone Promoted by Chitosan Ester Ruthenium Complex

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