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化学学报 >

2012 , Vol. 70 >Issue 03: 297 - 302

DOI: https://doi.org/10.6023/A1111141

研究论文

金鸡纳碱衍生物修饰的负载钌-铑双金属催化剂催化芳香酮不对称加氢

  • 蒋和雁 ,
  • 陈华
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  • a 重庆工商大学药物化学与化学生物学研究中心 重庆高校催化理论与应用技术市级重点实验室 重庆 400067;
    b 四川大学化学学院有机金属络合催化研究所 绿色化学及技术教育部重点实验室 成都 610064

收稿日期: 2011-11-14

  修回日期: 2011-12-01

  网络出版日期: 2011-12-01

基金资助

重庆市科委自然科学基金计划(No. CSTC, 2011BA5025)、重庆市教委自然科学基金(No. KJ100701)、重庆工商大学科研启动基金(No. 2010-56-14)和重庆市科技创新团队(No. KJTD201020)资助项目.

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Asymmetric Hydrogenation of Aromatic Ketones Catalyzed by Cinchona- and PPh3-Modified RuRh/γ-Al2O3

  • JIANG He-Yan ,
  • CHEN Hua
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  • a Research Center of Pharmaceutical Chemistry and Chemical Biology, Key Laboratory of Catalysis Science and Technology of Chongqing Education Commission, Chongqing Technology and Business University, Chongqing 400067;
    b Key Lab of Green Chemistry and Technology, Ministry of Education, The Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, Chengdu 610064

Received date: 2011-11-14

  Revised date: 2011-12-01

  Online published: 2011-12-01

Supported by

Project supported by Natural Science Foundation Project of CQ (No. CSTC, 2011BA5025), Ministry of Education of Chongqing (No. KJ100701), Chongqing Technology and Business University (No. 2010-56-14) and Chongqing Innovative Research Team Development Program in University (No. KJTD201020).

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摘要

以金鸡纳碱衍生物作为手性修饰剂, 研究了三苯基膦稳定的1.0% Ru+0.2% Rh/γ-Al2O3 催化剂催化芳香酮多相不对称加氢, 考察了修饰剂种类及浓度、碱添加剂种类及浓度、溶剂、氢气压力等因素对不对称加氢反应的影响. 结果表明, 金鸡纳碱衍生物对1.0% Ru+0.2% Rh/γ-Al2O3-tpp 催化剂具有较好的修饰作用, 在优化反应条件下苯乙酮加氢反应的对映选择性高达84%.

关键词： 钌; 铑; 金鸡纳碱; 芳香酮; 不对称加氢

本文引用格式

蒋和雁 , 陈华 . 金鸡纳碱衍生物修饰的负载钌-铑双金属催化剂催化芳香酮不对称加氢[J]. 化学学报, 2012 , 70(03) : 297 -302 . DOI: 10.6023/A1111141

Abstract

The asymmetric hydrogenation of aromatic ketones catalyzed by cinchona- and PPh3-modified 1.0% Ru+0.2% Rh/γ-Al2O3 was studied. The effects of different modifiers, modifier concentration, different base additives, base additive concentration, solvents, and hydrogen pressure on the asymmetric hydrogenation of aromatic ketones were investigated in detail. The results showed that cinchona alkaloids had good modification effects on the 1.0% Ru+0.2% Rh/γ-Al2O3-tpp catalyst. Under the optimum conditions, the hydrogenation enantioselectivity of acetophenone was up to 84%.

Key words： ruthenium; rhodium; cinchona alkaloids; aromatic ketones; asymmetric hydrogenation

参考文献

1 Noyori, R.; Ohkuma, T. Pure Appl. Chem. 1999, 71, 1495.

2 Li, Y. M.; Fan, Q. H.; Chan, A. S. C. Asymmetric Organic Reactions, Chemical Industry Press, Beijing, 2003, p. 57 (in Chinese). (李月明, 范青华, 陈新滋, 不对称有机反应, 化学工业 出版社, 北京, 2003, p. 57.)  

3 Wang, Y. Z.; Qiao, M. H.; Hu, H. R.; Yan, S. R.; Wang, W. J.; Fan, K. N. Acta Chim. Sinica 2004, 62, 1349 (in Chinese). (王友臻, 乔明华, 胡华荣, 闫世润, 王卫江, 范康 年, 化学学报, 2004, 62, 1349.)

4 Noyori, R.; Ohkuma, T. Angew. Chem., Int. Ed. 2001, 40, 40.  

5 Fehring, V.; Selke, R. Angew. Chem., Int. Ed. 1998, 37, 1827.  

6 Corey, E. J.; Bakshi, R. K.; Shibata, S. J. Am. Chem., Soc. 1987, 109, 5551.  

7 Ohkuma, T.; Ooka, H.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 10417.  

8 Doucet, H.; Ohkuma, T.; Murata, K.; Yokozawa, T.; Kozawa, M.; Katayama, E.; England, A. F.; Ikariya, T.; Noyori, R. Angew. Chem., Int. Ed. 1998, 37, 1703.  

9 Hashiguchi, S.; Fujii, A.; Takehara, J.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1995, 117, 7562.  

10 Chen, J. S.; Chen, L. L.; Xing, Y.; Chen, G.; Shen, W. Y.; Dong, Z. R.; Li, Y. Y.; Gao, J. X. Acta Chim. Sinica 2004, 62, 1745 (in Chinese). (陈建珊, 陈玲玲, 邢雁, 陈贵, 沈伟艺, 董振荣, 李岩云, 高景星, 化学学报, 2004, 62, 1745.)

11 Hu, J.; Zhao, G.; Ding, Z. Angew. Chem., Int. Ed. 2001, 40, 1109.  

12 Ohkuma, T.; Takeno, H.; Honda, Y.; Noyori, R. Adv. Synth. Catal. 2001, 343, 369.  

13 Hu, A.; Yee, G. T.; Lin, W. J. Am. Chem. Soc. 2005, 127, 12486.  

14 Itsuno, S.; Tsuji, A.; Takahashi, M. J. Polym. Sci. 2004, 42, 4556.

15 Bayston, D. J.; Travers, C. B.; Polywka, M. E. C. Tetrahedron: Asymmetry 1998, 9, 2015.  

16 Izumi, Y.; Imaida, M.; Fuawa, H. Bull. Chem. Soc. Jpn. 1963, 36, 21.  

17 Orito, Y.; Imai, S.; Niwa, S. J. Chem. Soc. Jpn. 1979, 1118.

18 Tungler, A.; Fogassy, G. J. Mol. Catal. A: Chem. 2001, 173, 231.  

19 Hess, R.; Vargas, A.; Mallat, T.; Burgi, T.; Baiker, A. J. Catal. 2004, 222, 117.  

20 Ye, L.; Lin, H.; Zhou, H.; Yuan, Y. J. Phys. Chem. C 2010, 114, 19752.  

21 Huang, Y. Y.; Ma, H. X.; Xiong, W.; Chen, H.; Li, X. J. Chin. J. Catal. 2004, 25, 962 (in Chinese). (黄艳轶, 马红霞, 熊伟, 陈华, 李贤均, 催化学报, 2004, 25, 962.)

22 Xiong, W.; Huang, Y. Y.; Chen, H.; Li, X. J. Acta Chim. Sinica 2005, 63, 1927 (in Chinese). (熊伟, 黄艳轶, 陈华, 李贤均, 化学学报, 2005, 63, 1927.)

23 Liu, D. R.; Xiong, W.; Yang, C. F.; Wang, J. B.; Chen, H.; Li, R. X.; Li, X. J. Acta Phys. Chim. Sin. 2007, 23, 479 (in Chinese). (刘德蓉, 熊伟, 杨朝芬, 王金波, 陈华, 李瑞祥, 李贤均, 物理化学学报, 2007, 23, 479.)  

24 Jiang, H. Y.; Chen, H.; Li, R. X. Catal. Commun. 2010, 11, 584.  

25 Xiong, W.; Liu, D. R.; Jia, Y.; Qin, R. X.; Qiu, H. D.; Wang, J. B.; Li, X. J. Chin. J. Catal. 2011, 32, 1275 (in Chinese). (熊伟, 刘德蓉, 贾云, 秦瑞香, 邱会东, 王金波, 李贤均, 催化学报, 2011, 32, 1275.)

26 Jiang, H. Y.; Yang, C. F.; Li, C.; Fu, H. Y.; Chen, H.; Li, R. X.; Li, X. J. Angew. Chem., Int. Ed. 2008, 47, 9240.  

27 Yang, C. F.; Jiang, H. Y.; Feng, J.; Fu, H. Y.; Li, R. X.; Chen, H.; Li, X. J. J. Mol. Catal. A: Chem. 2009, 300, 98.  

28 He, W.; Zhang, B. L.; Jiang, R.; Liu, P.; Sun, X. L.; Zhang, S. Y. Tetrahedron Lett. 2006, 47, 5367.  

29 Blaser, H. U.; Jalett, H. P.; Lottenbach, W.; Studer, M. J. Am. Chem. Soc. 2000, 122, 12675.  

30 Hoxha, F.; Königsmann, L.; Vargas, A.; Ferri, D.; Mallat, T.; Baiker, A. J. Am. Chem. Soc. 2007, 129, 10582.  

31 Ma, H. X.; Chen, H.; Zhang, Q.; Li, X. J. J. Mol. Catal. A: Chem. 2003, 196, 131.  

32 Huang, Y. L.; Chen, J. R.; Chen, H.; Li, R. X.; Li, Y. Z.; Min, L.-E.; Li, X. J. J. Mol. Catal. A: Chem. 2001, 170, 143.  

33 Xiong, W.; Ma, H. X.; Hong, Y. Y.; Chen, H.; Li, X. J. Tetrahedron: Asymmetry 2005, 16, 1449.  

34 Xiong, W.; Huang, Y. L.; Ma, H. X.; Chen, H.; Li, Y. Z.; Li, L. L.; Cheng, P. M.; Li, X. J. Acta Chim. Sinica 2003, 61, 922 (in Chinese). (熊伟, 黄裕林, 马红霞, 陈华, 黎耀忠, 李蕾蕾, 程溥明, 李贤均, 化学学报, 2003, 61, 922.)

35 Marzialetti, T.; Oportus, M.; Ruiz, D.; Fierro, J. L. G.; Reyes, P. Catal. Today 2008, 133～135, 711.  

36 Studer, M.; Blaser, H. U.; Exner, C. Adv. Synth. Catal. 2003, 345, 45.  

37 Perosa, A.; Tundo, P.; Selva, M. J. Mol. Catal. A: Chem. 2002, 180, 169.  

38 Chen, H. Y.; Hao, J. M.; Wang, H. J.; Xi, C. Y.; Meng, X. C.; Cai, S. X.; Zhao, F. Y. J. Mol. Catal. A: Chem. 2007, 278, 6.  

39 Tang, B.; Xiong, W.; Liu, D. R.; Jia, Y.; Wang, J. B.; Chen, H.; Li, X. J. Tetrahedron: Asymmetry 2008, 19, 1397.  
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