Citation: Tan-Yu Cheng, Jing-Lan Zhuang, Hui Yao, Huai-Sheng Zhang, Guo-Hua Liu. Immobilization of chiral Rh catalyst on glass and application to asymmetric transfer hydrogenation of aryl ketones in aqueous media[J]. Chinese Chemical Letters, ;2014, 25(4): 613-616. doi: 10.1016/j.cclet.2014.01.007 shu

Immobilization of chiral Rh catalyst on glass and application to asymmetric transfer hydrogenation of aryl ketones in aqueous media

1.
Key Laboratory of Resource Chemistry of Ministry of Education, College of Life and Environmental Science, Shanghai Normal University, Shanghai 200234, China

Corresponding author: Tan-Yu Cheng, Guo-Hua Liu,
Received Date: 7 October 2013
Available Online: 24 December 2013

A chiral catalyst, Cp^*RhTsDPEN (Cp^* = pentamethyl cyclopentadiene, TsDPEN = substitutive phenylsulfonyl-1,2-diphenylethylenediamine), was synthesized and immobilized at the surface of glass. The immobilized catalyst exhibited good catalytic efficiency for asymmetric transfer hydrogenation of aromatic ketones in water with HCOONa as hydrogen source.
- Heterogeneous Rh catalyst,
- Asymmetric transfer hydrogenation,
- Aromatic ketones,
- Glass substrate
1. [1]
  [1] R. Hong, G. Han, J.M. Fernández, et al., Glutathione-mediated delivery and release using monolayer protected nanoparticle carriers, J. Am. Chem. Soc. 128 (2006) 1078-1079.
2. [2]
  [2] P.D. Jadzinsky, G. Calero, C.J. Ackerson, D.A. Bushnell, R.D. Kornberg, Structure of a thiol monolayer-protected gold nanoparticle at 1.1A? resolution, Science 318 (2007) 430-433.
3. [3]
  [3] A. Verma, O. Uzun, Y. Hu, et al., Surface-structure-regulated cell-membrane penetration by monolayer-protected nanoparticles, Nat. Mater. 7 (2008) 588- 595.
4. [4]
  [4] G. He, G. Zhang, F. Lu, Y. Fang, Fluorescent film sensor for vapor-phase nitroaromatic explosives via monolayer assembly of oligo(diphenylsilane) on glass plate surfaces, Chem. Mater. 21 (2009) 1494-1499.
5. [5]
  [5] L. Ding, Y. Liu, Y. Cao, et al., A single fluorescent self-assembled monolayer film sensor with discriminatory power, J. Mater. Chem. 22 (2012) 11574-11582.
6. [6]
  [6] S. Zhang, F. Lü, L. Gao, L. Ding, Y. Fang, Fluorescent sensors for nitroaromatic compounds based on monolayer assembly of polycyclic aromatics, Langmuir 23 (2006) 1584-1590.
7. [7]
  [7] N.P. Reynolds, J.D. Tucker, P.A. Davison, et al., Site-specific immobilization and micrometer and nanometer scale photopatterning of yellow fluorescent protein on glass surfaces, J. Am. Chem. Soc. 131 (2009) 896-897.
8. [8]
  [8] S. Nakagaki, A.R. Ramos, F.L. Benedito, P.G. Peralta-Zamora, A.J.G. Zarbin, Immobilization of iron porphyrins into porous vycor glass: characterization and study of catalytic activity, J. Mol. Catal. A: Chem. 185 (2002) 203-210.
9. [9]
  [9] I.O. Benítez, B. Bujoli, L.J. Camus, et al., Monolayers as models for supported catalysts: zirconium phosphonate films containing manganese(ⅡI) porphyrins, J. Am. Chem. Soc. 124 (2002) 4363-4370.
10. [10]
  [10] X. Wu, C. Wang, J. Xiao, Asymmetric transfer hydrogenation in water with platinum group metal catalysts, Platinum Met. Rev. 54 (2010) 3-19.
11. [11]
  [11] R. Malacea, R. Poli, E. Manoury, Asymmetric hydrosilylation, transfer hydrogenation and hydrogenation of ketones catalyzed by iridium complexes, Coordin. Chem. Rev. 254 (2010) 729-752.
12. [12]
  [12] T. Jerphagnon, R. Haak, F. Berthiol, et al., Ruthenacycles and iridacycles as catalysts for asymmetric transfer hydrogenation and racemisation, Top. Catal. 53 (2010) 1002-1008.
13. [13]
  [13] C. Wang, X. Wu, J. Xiao, Broader, greener, and more efficient: recent advances in asymmetric transfer hydrogenation, Chem. Asian J. 3 (2008) 1750-1770.
14. [14]
  [14] T. Ikariya, A.J. Blacker, Asymmetric transfer hydrogenation of ketones with bifunctional transition metal-based molecular catalysts, Acc. Chem. Res. 40 (2007) 1300-1308.
15. [15]
  [15] S. Gladiali, E. Alberico, Asymmetric transfer hydrogenation: chiral ligands and applications, Chem. Soc. Rev. 35 (2006) 226-236.
16. [16]
  [16] C. Bianchini, P. Barbaro, Recent aspects of asymmetric catalysis by immobilized chiral metal catalysts, Top. Catal. 19 (2002) 17-32.
17. [17]
  [17] G. Zassinovich, G. Mestroni, S. Gladiali, Asymmetric hydrogen transfer reactions promoted by homogeneous transition metal catalysts, Chem. Rev. 92 (1992) 1051-1069.
18. [18]
  [18] S. Hashiguchi, A. Fujii, J. Takehara, T. Ikariya, R. Noyori, Asymmetric transfer hydrogenation of aromatic ketones catalyzed by chiral ruthenium(Ⅱ) complexes, J. Am. Chem. Soc. 117 (1995) 7562-7563.
19. [19]
  [19] R. Noyori, S. Hashiguchi, Asymmetric transfer hydrogenation catalyzed by chiral ruthenium complexes, Acc. Chem. Res. 30 (1997) 97-102.
20. [20]
  [20] R. Noyori, Asymmetric catalysis: science and opportunities (Nobel Lecture), Angew. Chem. Int. Ed. 41 (2002) 2008-2022.
21. [21]
  [21] S. Minakata, M. Komatsu, Organic reactions on silica in water, Chem. Rev. 109 (2008) 711-724.
22. [22]
  [22] C. Li, Chiral synthesis on catalysts immobilized in microporous and mesoporous materials, Catal. Rev. 46 (2004) 419-492.
23. [23]
  [23] S. Shylesh, V. Schünemann, W.R. Thiel, Magnetically separable nanocatalysts: bridges between homogeneous and heterogeneous catalysis, Angew. Chem. Int. Ed. 49 (2010) 3428-3459.
24. [24]
  [24] T. Maschmeyer, F. Rey, G. Sankar, J.M. Thomas, Heterogeneous catalysts obtained by grafting metallocene complexes onto mesoporous silica, Nature 378 (1995) 159-162.
25. [25]
  [25] J. Lu, P.H. Toy, Organic polymer supports for synthesis and for reagent and catalyst immobilization, Chem. Rev. 109 (2009) 815-838.
26. [26]
  [26] S.C. Petrosius, R.S. Drago, V. Young, G.C. Grunewald, Low-temperature decomposition of some halogenated hydrocarbons using metal oxide/porous carbon catalysts, J. Am. Chem. Soc. 115 (1993) 6131-6137.
27. [27]
  [27] H. Zhang, R. Jin, H. Yao, et al., Core-shell structured mesoporous silica: a new immobilized strategy for rhodium catalyzed asymmetric transfer hydrogenation, Chem. Commun. 48 (2012) 7874-7876.
28. [28]
  [28] Y. Sun, G. Liu, H. Gu, et al., Magnetically recoverable SiO2-coated Fe₃O₄ nanoparticles: a new platform for asymmetric transfer hydrogenation of aromatic ketones in aqueous medium, Chem. Commun. 47 (2011) 2583- 2585.
29. [29]
  [29] G. Liu, H. Gu, Y. Sun, et al., Magnetically recoverable nanoparticles: highly efficient catalysts for asymmetric transfer hydrogenation of aromatic ketones in aqueous medium, Adv. Synth. Catal. 353 (2011) 1317-1324.
30. [30]
  [30] G. Liu, J. Wang, T. Huang, et al., Mesoporous silica-supported iridium catalysts for asymmetric hydrogenation reactions, J. Mater. Chem. 20 (2010) 1970-1975.
31. [31]
  [31] G. Liu, Y. Sun, J. Wang, et al., Microwave-assisted tandem allylation-isomerization reaction catalyzed by a mesostructured bifunctional catalyst in aqueous media, Green Chem. 11 (2009) 1477-1481.
32. [32]
  [32] X. Wu, X. Li, A. Zanotti-Gerosa, et al., RhⅡI- and IrⅡI-catalyzed asymmetric transfer hydrogenation of ketones in water, Chem. Eur. J. 14 (2008) 2209-2222.
1. [1]
  Ming Huang , Xiuju Cai , Yan Liu , Zhuofeng Ke . Base-controlled NHC-Ru-catalyzed transfer hydrogenation and α-methylation/transfer hydrogenation of ketones using methanol. Chinese Chemical Letters, 2024, 35(7): 109323-. doi: 10.1016/j.cclet.2023.109323
2. [2]
  Chao Chen , Wenwen Yu , Guangen Huang , Xuelian Ren , Xiangli Chen , Yixin Li , Shenggui Liang , Mengmeng Xu , Mingyue Zheng , Yaxi Yang , He Huang , Wei Tang , Bing Zhou . Asymmetric macrocyclization enabled by Rh(Ⅲ)-catalyzed CH activation: Enantioenriched macrocyclic inhibitor of Zika virus infection. Chinese Chemical Letters, 2024, 35(11): 109574-. doi: 10.1016/j.cclet.2024.109574
3. [3]
  Ruixue Liu , Xiaobing Ding , Qiwei Lang , Gen-Qiang Chen , Xumu Zhang . Enantioselective and divergent construction of chiral amino alcohols and oxazolidin-2-ones via Ir-f-phamidol-catalyzed dynamic kinetic asymmetric hydrogenation. Chinese Chemical Letters, 2025, 36(3): 110037-. doi: 10.1016/j.cclet.2024.110037
4. [4]
  Wen-Jing Li , Jun-Bo Wang , Yu-Heng Liu , Mo Zhang , Zhan-Hui Zhang . Molybdenum-doped carbon nitride as an efficient heterogeneous catalyst for direct amination of nitroarenes with arylboronic acids. Chinese Chemical Letters, 2025, 36(3): 110001-. doi: 10.1016/j.cclet.2024.110001
5. [5]
  Weichen Zhu , Wei Zuo , Pu Wang , Wei Zhan , Jun Zhang , Lipin Li , Yu Tian , Hong Qi , Rui Huang . Fe-N-C heterogeneous Fenton-like catalyst for the degradation of tetracycline: Fe-N coordination and mechanism studies. Chinese Chemical Letters, 2024, 35(9): 109341-. doi: 10.1016/j.cclet.2023.109341
6. [6]
  Zhichao Zhou , Fuqian Chen , Xiaotong Xia , Dong Ye , Rong Zhou , Lei Li , Tao Deng , Zhenhua Ding , Fang Liu . Developing a fluorescence substrate for HRP-based diagnostic assays with superiorities over the commercial ADHP. Chinese Chemical Letters, 2024, 35(6): 108970-. doi: 10.1016/j.cclet.2023.108970
7. [7]
  Chunhui Zhang , Jie Wang , Jieyang Zhan , Runmin Yang , Guanggang Gao , Jiayuan Zhang , Linlin Fan , Mengqi Wang , Hong Liu . Highly sensitive hydrazine detection through a novel Raman scattering quenching mechanism enabled by a crystalline and noble metal–free polyoxometalate substrate. Chinese Chemical Letters, 2025, 36(3): 109719-. doi: 10.1016/j.cclet.2024.109719
8. [8]
  Jingyu Chen , Sha Wu , Yuhao Wang , Jiong Zhou . Near-perfect separation of alicyclic ketones and alicyclic alcohols by nonporous adaptive crystals of perethylated pillar[5]arene and pillar[6]arene. Chinese Chemical Letters, 2025, 36(4): 110102-. doi: 10.1016/j.cclet.2024.110102
9. [9]
  Yuanjiao Liu , Xiaoyang Zhao , Songyao Zhang , Yi Wang , Yutuo Zheng , Xinrui Miao , Wenli Deng . Site-selection and recognition of aromatic carboxylic acid in response to coronene and pyridine derivative. Chinese Chemical Letters, 2024, 35(8): 109404-. doi: 10.1016/j.cclet.2023.109404
10. [10]
  Hong Zhang , Cui-Ping Li , Li-Li Wang , Zhuo-Da Zhou , Wen-Sen Li , Ling-Yi Kong , Ming-Hua Yang . Asperochones A and B, two antimicrobial aromatic polyketides from the endophytic fungus Aspergillus sp. MMC-2. Chinese Chemical Letters, 2024, 35(9): 109351-. doi: 10.1016/j.cclet.2023.109351
11. [11]
  Dongying Fu , Lin Pan , Yanli Ma , Yue Zhang . Bilayered Dion–Jacobson lead-iodine hybrid perovskite with aromatic spacer for broadband photodetection. Chinese Chemical Letters, 2025, 36(2): 109621-. doi: 10.1016/j.cclet.2024.109621
12. [12]
  Tingting Huang , Zhuanlong Ding , Hao Liu , Ping-An Chen , Longfeng Zhao , Yuanyuan Hu , Yifan Yao , Kun Yang , Zebing Zeng . Electron-transporting boron-doped polycyclic aromatic hydrocarbons: Facile synthesis and heteroatom doping positions-modulated optoelectronic properties. Chinese Chemical Letters, 2024, 35(4): 109117-. doi: 10.1016/j.cclet.2023.109117
13. [13]
  Junjun Huang , Ran Chen , Yajian Huang , Hang Zhang , Anran Zheng , Qing Xiao , Dan Wu , Ruxia Duan , Zhi Zhou , Fei He , Wei Yi . Discovery of an enantiopure N-[2-hydroxy-3-phenyl piperazine propyl]-aromatic carboxamide derivative as highly selective α_1D/1A-adrenoceptor antagonist and homology modelling. Chinese Chemical Letters, 2024, 35(11): 109594-. doi: 10.1016/j.cclet.2024.109594
14. [14]
  Rui HUANG , Shengjie LIU , Qingyuan WU , Nanfeng ZHENG . Enhanced selectivity of catalytic hydrogenation of halogenated nitroaromatics by interfacial effects. Chinese Journal of Inorganic Chemistry, 2025, 41(1): 201-212. doi: 10.11862/CJIC.20240356
15. [15]
  Minghui Zhang , Na Zhang , Qian Zhao , Chao Wang , Alexander Steiner , Jianliang Xiao , Weijun Tang . Cobalt pincer complex-catalyzed highly enantioselective hydrogenation of quinoxalines. Chinese Chemical Letters, 2025, 36(4): 110081-. doi: 10.1016/j.cclet.2024.110081
16. [16]
  Long Jin , Jian Han , Dongmei Fang , Min Wang , Jian Liao . Pd-catalyzed asymmetric carbonyl alkynylation: Synthesis of axial chiral ynones. Chinese Chemical Letters, 2024, 35(6): 109212-. doi: 10.1016/j.cclet.2023.109212
17. [17]
  Pei Cao , Yilan Wang , Lejian Yu , Miao Wang , Liming Zhao , Xu Hou . Dynamic asymmetric mechanical responsive carbon nanotube fiber for ionic logic gate. Chinese Chemical Letters, 2024, 35(6): 109421-. doi: 10.1016/j.cclet.2023.109421
18. [18]
  Heng Yang , Zhijie Zhou , Conghui Tang , Feng Chen . Recent advances in heterogeneous hydrosilylation of unsaturated carbon-carbon bonds. Chinese Chemical Letters, 2024, 35(6): 109257-. doi: 10.1016/j.cclet.2023.109257
19. [19]
  Hao-Cong Li , Ming Zhang , Qiyan Lv , Kai Sun , Xiao-Lan Chen , Lingbo Qu , Bing Yu . Homogeneous catalysis and heterogeneous separation: Ionic liquids as recyclable photocatalysts for hydroacylation of olefins. Chinese Chemical Letters, 2025, 36(2): 110579-. doi: 10.1016/j.cclet.2024.110579
20. [20]
  Xiaoyu Zhang , Xin Yu . Solar-powered heterogeneous water disinfection nano-system. Chinese Journal of Structural Chemistry, 2025, 44(3): 100439-100439. doi: 10.1016/j.cjsc.2024.100439

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(634)
HTML views(3)

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