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
1. [1]
  Lihui Jiang , Wanrong Dong , Hua Yang , Yongqing Xia , Hongjian Peng , Jun Yuan , Xiaoqian Hu , Zihan Zeng , Yingping Zou , Yiming Luo . Study on Extraction of p-Hydroxyacetophenone. University Chemistry, 2024, 39(11): 259-268. doi: 10.12461/PKU.DXHX202402056
2. [2]
  Yongqing Kuang , Jie Liu , Jianjun Feng , Wen Yang , Shuanglian Cai , Ling Shi . Experimental Design for the Two-Step Synthesis of Paracetamol from 4-Hydroxyacetophenone. University Chemistry, 2024, 39(8): 331-337. doi: 10.12461/PKU.DXHX202403012
3. [3]
  Jingke LIU , Jia CHEN , Yingchao HAN . Nano hydroxyapatite stable suspension system: Preparation and cobalt adsorption performance. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1763-1774. doi: 10.11862/CJIC.20240060
4. [4]
  Hong Lu , Yidie Zhai , Xingxing Cheng , Yujia Gao , Qing Wei , Hao Wei . Advancements and Expansions in the Proline-Catalyzed Asymmetric Aldol Reaction. University Chemistry, 2024, 39(5): 154-162. doi: 10.3866/PKU.DXHX202310074
5. [5]
  Jin Tong , Shuyan Yu . Crystal Engineering for Supramolecular Chirality. University Chemistry, 2024, 39(3): 86-93. doi: 10.3866/PKU.DXHX202308113
6. [6]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
7. [7]
  Haiying Wang , Andrew C.-H. Sue . How to Visually Identify Homochiral Crystals. University Chemistry, 2024, 39(3): 78-85. doi: 10.3866/PKU.DXHX202309004
8. [8]
  Keying Qu , Jie Li , Ziqiu Lai , Kai Chen . Unveiling the Mystery of Chirality from Tartaric Acid. University Chemistry, 2024, 39(9): 369-378. doi: 10.12461/PKU.DXHX202310091
9. [9]
  Xilin Zhao , Xingyu Tu , Zongxuan Li , Rui Dong , Bo Jiang , Zhiwei Miao . Research Progress in Enantioselective Synthesis of Axial Chiral Compounds. University Chemistry, 2024, 39(11): 158-173. doi: 10.12461/PKU.DXHX202403106
10. [10]
  Conghao Shi , Ranran Wang , Juli Jiang , Leyong Wang . The Illustration on Stereoisomers of Macrocycles Containing Multiple Chiral Centers via Tröger Base-based Macrocycles. University Chemistry, 2024, 39(7): 394-397. doi: 10.3866/PKU.DXHX202311034
11. [11]
  Tingyu Zhu , Hui Zhang , Wenwei Zhang . Exploration and Practice of Ideological and Political Education in the Course of Experiments on Chemical Functional Molecules: Synthesis and Catalytic Performance Study of Chiral Mn(III)Cl-Salen Complex. University Chemistry, 2024, 39(4): 75-80. doi: 10.3866/PKU.DXHX202311011
12. [12]
  Yan Li , Xinze Wang , Xue Yao , Shouyun Yu . Kinetic Resolution Enabled by Photoexcited Chiral Copper Complex-Mediated Alkene E→Z Isomerization: A Comprehensive Chemistry Experiment for Undergraduate Students. University Chemistry, 2024, 39(5): 1-10. doi: 10.3866/PKU.DXHX202309053
13. [13]
  Wenlong LI , Xinyu JIA , Jie LING , Mengdan MA , Anning ZHOU . Photothermal catalytic CO₂ hydrogenation over a Mg-doped In₂O_3-x catalyst. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 919-929. doi: 10.11862/CJIC.20230421
14. [14]
  Yinuo Wang , Siran Wang , Yilong Zhao , Dazhen Xu . Selective Synthesis of Diarylmethyl Anilines and Triarylmethanes via Multicomponent Reactions: Introduce a Comprehensive Experiment of Organic Chemistry. University Chemistry, 2024, 39(8): 324-330. doi: 10.3866/PKU.DXHX202401063
15. [15]
  Heng Chen , Longhui Nie , Kai Xu , Yiqiong Yang , Caihong Fang . 两步焙烧法制备大比表面积和结晶性增强超薄g-C₃N₄纳米片及其高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406019-. doi: 10.3866/PKU.WHXB202406019
16. [16]
  Cheng PENG , Jianwei WEI , Yating CHEN , Nan HU , Hui ZENG . First principles investigation about interference effects of electronic and optical properties of inorganic and lead-free perovskite Cs₃Bi₂X₉ (X=Cl, Br, I). Chinese Journal of Inorganic Chemistry, 2024, 40(3): 555-560. doi: 10.11862/CJIC.20230282
17. [17]
  Xiaowu Zhang , Pai Liu , Qishen Huang , Shufeng Pang , Zhiming Gao , Yunhong Zhang . Acid-Base Dissociation Equilibrium in Multiphase System: Effect of Gas. University Chemistry, 2024, 39(4): 387-394. doi: 10.3866/PKU.DXHX202310021
18. [18]
  Chengqian Mao , Yanghan Chen , Haotong Bai , Junru Huang , Junpeng Zhuang . Photodimerization of Styrylpyridinium Salt and Its Application in Silk Screen Printing. University Chemistry, 2024, 39(5): 354-362. doi: 10.3866/PKU.DXHX202312014
19. [19]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001
20. [20]
  Liangzhen Hu , Li Ni , Ziyi Liu , Xiaohui Zhang , Bo Qin , Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001

Get Citation

PDF

XML

Metrics

PDF Downloads(1089)
Abstract views(2976)
HTML views(54)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142

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

Metrics

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