Citation: ZHANG Ding-Lin, YANG Chao-Fen, SUN Ya-Ping, FU Hai-Yan, LI Rui-Xiang, CHEN Hua, LI Xian-Jun. Asymmetric Hydrogenation of Acetophenone Catalyzed by RuCl₂(TPP)₃ Supported on Hydroxyapatite Modified with Chiral Amine[J]. Acta Physico-Chimica Sinica, ;2010, 26(10): 2711-2718. doi: 10.3866/PKU.WHXB20101017 shu

Asymmetric Hydrogenation of Acetophenone Catalyzed by RuCl₂(TPP)₃ Supported on Hydroxyapatite Modified with Chiral Amine

1.
1. Key Laboratory of Green Chemistry and Technology, Ministry of Education, Institute of Homogeneous Catalysis, College of Chemistry, Sichuan University, Chengdu 610064, P. R. China;
2. Department of Chemistry, School of Pharmacy,The Third Military Medical University, Chongqing 400038, P. R. China

Received Date: 22 April 2010
Available Online: 27 September 2010

Chiral amine (L-proline,D-proline, (1R,2R)-1,2 -diphenyl -1,2 -ethylene diamine sulfonate disodium ((1R, 2R)-DPENDS) and (1S,2S)-1,2 -diphenyl -1,2 -ethylene diamine sulfonate disodium ((1S,2S)-DPENDS)) modified hydroxyapatite (HAP) were prepared and characterized by Fourier transform infrared (FT -IR) spectrometry, scanning electron microscopy (SEM),X-ray diffraction (XRD), and Brunauer -Emmett -Teller (BET) surface area analysis. RuCl₂ (TPP)₃was supported on(1R,2R)-DPENDS modified HAP for the asymmetric hydrogenation of acetophenone. A detailed investigation about the effects of temperature, amount of alkali,H₂ pressure, and concentration of DPENDS modified HAP on the activity and enantioselectivity of acetophenone hydrogenation was undertaken. Under the optimum reaction conditions of 30 ^oC, p(H₂)=5.0 MPa, reaction time of 4 h, the conversion and enantioselectivity reached 99.9% and 77.8% enantiomeric excess (ee), respectively. The results indicated that the asymmetric hydrogenation was accomplished on the surface of the chiral amine modified HAP. The immobilized catalyst was separated from the products by simple centrifugation and reused without adding any other reagents.
- Chiral amine,
- Hydroxyapatite,
- RuCl₂(TPP)₃,
- Acetophenone,
- Heterogeneous asymmetrichydrogenation
1. [1]
  
  1. Noyori, R.; Ohkuma, T. Angew. Chem. Int. Edit., 2001, 40(1): 40
2. [2]
  2. Noyori, R. Adv. Synth. Catal., 2003, 345(1-2): 15
3. [3]
  3. Vargas, A.; Ferri, D.; Bonalumi, N.; Mallat, T.; Baiker, A. Angew. Chem. Int. Edit., 2007, 46(21): 3905
4. [4]
  4. Cheng, H. Y.; Hao, J. M.; Wang, H. J.; Xi, C. Y.; Cheng, X. C.; Cai, S. X.; Zhao, F. Y. J. Mol. Catal. A-Chem., 2007, 278(1-2): 6
5. [5]
  5. Jiang, H. Y.; Yang, C. F.; Li, C.; Fu, H. Y.; Chen, H.; Li, R. X.; Li, X. J. Angew. Chem. Int. Edit., 2008, 47(48): 9240
6. [6]
  6. Tang, B.; Xiong, W.; Liu, E. R.; Jia, Y.; Wang, J. B.; Chen, H.; Li, X. J. Tetrahedron-Asymmetry, 2008, 19(11): 1397
7. [7]
  7. 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(1-2): 98
8. [8]
  8. Zhang, D. L.; Yang, C. F.; Feng, J.; Fu, H. Y.; Chen, H.; Li, R. X.; Li, X. J. Acta Phys. -Chim. Sin., 2009, 25(10): 2039 [张定林, 杨朝芬,冯建,付海燕,陈华,李瑞祥, 李贤均. 物理化学学报, 2009, 25(10): 2039]
9. [9]
  9. Yu, H. B.; Hu, Q. S.; Pu, L. Tetrahedron Lett., 2000, 41(11): 1681
10. [10]
  10. Takahashi, M.; Haraguchi, N.; Itsuno, S. Tetrahedron-Asymmetry, 2008, 19(1): 60
11. [11]
  11. Chiwara, V. I.; Haraguchi, N.; Itsuno, S. J. Org. Chem., 2009, 74 (3): 1391
12. [12]
  12. Chai, L. T.; Wang, W.W.; Wang, Q. R.; Tao, F. G. J. Mol. Catal. A-Chem., 2007, 270(1-2): 83
13. [13]
  13. Li, X. G.; Chen, W. P.; Hems, W.; King, F.; Xiao, J. L. Org. Lett., 2003, 5(24): 4559
14. [14]
  14. Hu, A. G.; N , H. L.; Lin, W. B. J. Am. Chem. Soc., 2003, 125 (38): 11490
15. [15]
  15. Kesanli, B.; Lin, W. B. Chem. Commun., 2004, (20): 2284
16. [16]
  16. Hu, A. G.; Yee, G. T.; Lin, W. B. J. Am. Chem. Soc., 2005, 127 (36): 12486
17. [17]
  17. Yang, H. Q.; Li, J.; Yang, J.; Liu, Z. M.; Yang, Q. H.; Li, C. Chem. Commun., 2007, (10): 1086
18. [18]
  18. Parambadath, S.; Singh, A. P. Catal. Today, 2009, 141(1-2): 161
19. [19]
  19. Tanaka, H.; Futaoka, M.; Hino, R. J. Colloid Interface Sci., 2004, 269(2): 358
20. [20]
  20. Tanaka, H.; Futaoka, M.; Hino, R.; Kandori, K.; Ishikawa, T. J. Colloid Interface Sci., 2005, 283(2): 609
21. [21]
  21. Tanaka, H.; Watanabe, T.; Chikazawa, M.; Kandori, K.; Ishikawa, T. Colloids Surf. A, 1998, 139(3): 341
22. [22]
  22. Ei-Hammari, L.; Marroun, H.; Laghzizil, A.; Saoiabi, A.; Roux, C.; Livage, J.; Coradin, T. J. Solid State Chem., 2008, 181(4): 848
23. [23]
  23. Borum-Nicholas, L.; Wilson, O. C. Biomaterials, 2003, 24(21): 3671
24. [24]
  24. Tanaka, H.; Watanabe, T.; Chikazawa, M.; Kandori, K.; Ishikawa, T. J. Colloid Interface Sci., 1999, 214(1): 31
25. [25]
  25. El Shafei, G. M. S.; Moussa, N. A. J. Colloid Interface Sci., 2001, 238(1): 160
26. [26]
  26. Matsumoto, T.; Okazaki, M.; Inoue, M.; Hamada, Y.; Taira, M.; Takahashi, J. Biomaterials, 2002, 23(10): 2241
27. [27]
  27. Zhang, Y.; Zhao, Y. W.; Xia, C. G. J. Mol. Catal. A-Chem., 2009, 306(1-2): 107
28. [28]
  28. Opre, Z.; Ferri, D.; Krumeich, F.; Mallat, T.; Baiker, A. J. Catal., 2006, 241(2): 287
29. [29]
  29. Ma, Y. P.; Liu, H.; Chen, L.; Cui, X.; Zhu, J.; Deng, J. G. Org. Lett., 2003, 5(12): 2103
30. [30]
  30. Hallman, P. S.; Stephenson, T. A.; Wilkinson, G. Inorg. Synth., 2007, 12: 237
31. [31]
  31. Sugiyama, S.; Minami, T.; Hayashi, H.; Tanaka, M.; Shigemoto, N.; Moffat, J. B. J. Chem. Soc. Faraday Trans., 1996, 92(2): 293
32. [32]
  32. Tungler, A.; Tarnai, T.; Máthé, T.; Petró, J. J. Mol. Catal., 1991, 67(2): 277
33. [33]
  33. Wang, L. L.; Lü, S. J.; Xia, C. G. J. Mol. Catal. (China), 2000, 14 (5): 345 [王来来, 吕世杰,夏春谷.分子催化, 2000, 14(5): 345]
34. [34]
  34. Chen, X. Y.; Lou, Z. Y.; Qiao, M. H.; Fan, K. N.; Tsang, S. H.; He, H. Y. J. Phys. Chem. C, 2008, 112(5): 1316
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Asymmetric Hydrogenation of Acetophenone Catalyzed by RuCl2(TPP)3 Supported on Hydroxyapatite Modified with Chiral Amine

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通讯作者: 陈斌, bchen63@163.com

Asymmetric Hydrogenation of Acetophenone Catalyzed by RuCl₂(TPP)₃ Supported on Hydroxyapatite Modified with Chiral Amine