Study on Synthesis of Imidazolium-Tagged Chiral Pyrphos Diphosphine Ligands and Their Applications in Asymmetric Hydrogenation

doi:10.6023/cjoc201305042

Chin. J. Org. Chem. ›› 2013, Vol. 33 ›› Issue (10): 2143-2147.DOI: 10.6023/cjoc201305042 Previous Articles Next Articles

Articles

咪唑型离子液负载手性双膦配体pyrphos的合成及不对称氢化研究

易兵^a,b, 武高峰^b, 周威^b, 何华平^a

a 湖南工程学院化学化工学院生态纺织材料及染整新技术湖南省高校重点实验室湘潭 411104;
b 湘潭大学化学学院环境友好化学与应用省部共建教育部重点实验室湘潭 411105

收稿日期:2013-05-30 修回日期:2013-07-06 发布日期:2013-07-10
通讯作者: 易兵 E-mail:bingyi2004@126.com
基金资助:
国家自然科学基金(Nos. 21172064, 20972045);湖南省自然科学基金(No. 10JJ2006)和湖南省教育厅重点(No. 10A022)资助项目

Study on Synthesis of Imidazolium-Tagged Chiral Pyrphos Diphosphine Ligands and Their Applications in Asymmetric Hydrogenation

Yi Bing^a,b, Wu Gaofeng^b, Zhou Wei^b, He Huaping^a

a Key Laboratory of Ecological Textile Materials & Novel Dying and Finishing Technology, Hunan Provincial Education Department, School of Chemistry & Chemical Engineering, Hunan Institute of Engineering, Xiangtan 411104;
b Key Laboratory of Environmentally Friendly Chemistry and Applications, Ministry of Education, School of Chemistry, Xiangtan University, Xiangtan 411105

Received:2013-05-30 Revised:2013-07-06 Published:2013-07-10
Supported by:
Project supported by the National Natural Science Foundation of China (Nos. 21172064, 20972045), the Natural Science Foundation of Hunan Province (No.10JJ2006), and the Key Scientific Research Fund of Hunan Provincial Education Department (No. 10A022).

1. Study on Synthesis of Imidazolium-Tagged Chiral Pyrphos Diphosphine Ligands and Their Applications in Asymmetric Hydrogenation.PDF(420KB)

Abstract

Herein we developed a facile method for preparation of a new functionalized ionic liquids supported chiral diphosphine ligands by grafting homogeneous chiral pyrphos[(R,R)-3,4-bis(diphenylphosphino)pyrrolidine] ligand with C₂ axis onto imidazolium ionic liquids supports. Firstly the linker groups having halogen atoms were attached to amino group in pyrphos, and then reacted with N-methylimidazole. The other anion-containing chiral ligands located on ionic liqids (ILs) were synthesized via ion exchange technique. These ligands and the related intermediates were purified by flash column chromatography and were characterized by ¹H NMR, ¹³C NMR, ³¹P NMR, IR and HRMS techniques. All results were consistent with the compounds synthesized. Then we focused on the catalytic performances and the feasibility of catalyst recycling in rhodium-catalyzed asymmetric hydrogenation of prechiral dehydroamino acid. The results showed that the catalyst generated in situ by imidazolium-tagged pyrphos ligands with BF₄ as counteranion and[Rh(COD)₂]BF₄ exhibited high catalytic activity and enantioselectivity in asymmetric hydrogenation of α-acetamido cinnamic acid in[bmim]BF₄/MeOH cosolvent systems, which was similar to the molecule catalyst. The conversion is 100%, and the ee value is up to 97.0%. Moreover, the catalyst could be reused four times without significant loss of activity and enantioselectivity.

Key words: asymmetric hydrogenation, diphosphine ligand, imidazolium ionic liquid, immobilization, catalyst recycling

Cite this article

Yi Bing, Wu Gaofeng, Zhou Wei, He Huaping. Study on Synthesis of Imidazolium-Tagged Chiral Pyrphos Diphosphine Ligands and Their Applications in Asymmetric Hydrogenation[J]. Chin. J. Org. Chem., 2013, 33(10): 2143-2147.

Export EndNote|Reference Manager|ProCite|BibTeX|RefWorks

share this article

References

[1] Noyori, R. Asymmetric Catalysis in Organic Synthesis, Wiley, New York, 1994.
[2] Lin, G. Q.; Li, Y. M.; Chan, A. S. C. Principles and Applications of Asymmetric Synthesis, Wiley-Interscience, New York, 2001.
[3] Xie, J. H.; Zhou, Q. L. Acta Chim. Sinica 2012, 70, 1427 (in Chinese).(谢建华, 周其林, 化学学报, 2012, 70, 1427.)
[4] Liu, Y.; Wang, Z.; Ding, K. L. Acta Chim. Sinica 2012, 70, 1464 (in Chinese).(刘龑, 王正, 丁奎岭, 化学学报, 2012, 70, 1464.)
[5] Li, C. J.; Chan, T. H. Organic Reaction in Aqueous Media, Wiley, New York, 1997.
[6] Pomogailo, A. D. Catalysis by Polymer-Immobilized Metal Complexes, Gordon & Breach, New York, USA, 1998.
[7] Jessop, P. G.; Leitner, W. Chemical Synthesis Using Supercritical Fluids, Wiley-WCH, Weinheim, 1999.
[8] Ding, K.; Uozumi, Y. Handbook of Asymmetric Heterogeneous Catalysis, Wiley-VCH, Weinherm, 2008.
[9] Fei, Z.; Geldbach, T. J.; Zhao, D.; Dyson, P. J. Chem. Eur. J. 2006, 12, 2122.
[10] Miao, W.; Chan, T. H. Acc. Chem. Res. 2006, 39, 897.
[11] Durand, J.; Teuma, E.; Gómez, M. C. R. Chimie 2007, 10, 1.
[12] Davoodnia, A.; Khojastehnezhad, A.; Bakavoli, M.; Tavakoli-Hoseini, N. Chin. J. Chem. 2011, 29, 978.
[13] Lee, S.; Zhang, Y. J.; Piao, J. Y.; Yoon, H.; Song, C. U.; Choi, J. H.; Hong, J. Chem. Commun. 2003, 2624.
[14] Fow, K. L.; Jaenicke, S.; Muller, T. E.; Sievers, C. J. Mol. Catal. A: Chem. 2008, 279, 239.
[15] Jin, X.; Xu, X.; Zhao, K. Tetrahedron: Asymmetry 2012, 23, 1058.
[16] Geldbach, T. J.; Dyson, P. J. J. Am. Chem. Soc. 2004, 126, 8114.
[17] Kawasaki, I.; Tsunoda, K.; Tsuji, T.; Yamaguchi, T.; Shibuta, H.; Uchida, N.; Yamashita, M.; Ohta, S. Chem. Commun. 2005, 2134.
[18] Xu, D.; Luo, S.; Yue, H.; Wang, L.; Liu, Y.; Xu, Z. Synlett 2006, 2569.
[19] Wu, L. Y.; Yan, Z. Y.; Xie, Y. X.; Niu, Y. N.; Liang, L. Tetrahedron: Asymmetry 2007, 18, 2086.
[20] Miao, W.; Chan, T. H. Adv. Synth. Catal. 2006, 348, 1711.
[21] Doherty, S.; Goodrich, P.; Hardacre, C.; Parvulescu, V.; Paun, C. Adv. Synth. Catal. 2008, 350, 295.
[22] Yi, B.; Fan, Q.; Deng, G. J.; Li, Y. M.; Chan, A. S. C. Org. Lett. 2004, 6, 1361.
[23] Deng, G. J.; Yi, B.; Huang, Y.; Tang, W.; Fan, Q. Adv. Synth. Catal. 2004, 346, 1440.
[24] Yi, B.; He, H.; Fan, Q. H. J. Mol. Catal., A: Chem. 2010, 315, 82.
[25] Xu, L. J.; Yi, B.; Dang, L. M.; Tang, W. J. Prog. Chem. 2010, 22, 1254 (in Chinese).(徐立进, 易兵, 党丽敏, 汤伟军, 化学进展, 2010, 22, 1254.)
[26] Yi, B.; Zhang, Y.; Shu, X. M.; Yang, Y.; Du, W. L.; Liu, Z. P. Chin. J. Org. Chem. 2011, 31, 874 (in Chinese).(易兵, 张阳, 束晓马, 杨艳, 杜文乐, 刘展鹏, 有机化学, 2011, 31, 874.)
[27] Pyrphos was first reported by Nagel and co-workers. See: Nagel, U.; Kinzel, E.; Andrade, J.; Prescher, G. Chem. Ber. 1986, 119, 3326.
[28] Schrock, R. R.; Osborn, J. A. J. Am. Chem. Soc. 1971, 93, 3089.

咪唑型离子液负载手性双膦配体pyrphos的合成及不对称氢化研究

Study on Synthesis of Imidazolium-Tagged Chiral Pyrphos Diphosphine Ligands and Their Applications in Asymmetric Hydrogenation

PDF

Supporting Info.

Knowledge

Cited

Abstract

Cite this article

share this article

References

Related Articles 15

Recommended Articles

Metrics

Comments

[1]	Yangyang Chu, Zhaobin Han, Kuiling Ding. Progresses in the Application of Kinetic Resolution in Transition Metal Catalyzed Asymmetric (Transfer) Hydrogenation [J]. Chinese Journal of Organic Chemistry, 2023, 43(6): 1934-1951.
[2]	Chenguang Liu, Qiang Liu. Earth-Abundant Metal-Catalyzed Asymmetric Hydrogenation of Carbon-Nitrogen Unsaturated Bonds [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3213-3220.
[3]	Yuxuan Zhang, Limin Xu, Yan Lu, Zhaoguo Zhang. Progress in Asymmetric Catalytic Reduction of Diketones [J]. Chinese Journal of Organic Chemistry, 2022, 42(10): 3221-3239.
[4]	Fang Zhao, Wenjing Ye, Kai Wang. Advancement of Chiral Monodentate Phosphite Ligands in Asymmetric Hydrogenation [J]. Chinese Journal of Organic Chemistry, 2021, 41(7): 2650-2665.
[5]	Li Sheng, Haoling Gao, Xufeng Wu, Gang Fan, Pengcheng Liu. Rhodium/(2S,2'S,3S,3'S)-3,3'-Di-tert-butyl-4,4'-dimethoxy-2,2',3,3'-tetrahydro-2,2'-bibenzo[d][1,3]oxaphosphole (MeO-BIBOP) Catalyzed Synthesis of (R)-3-tert-Butoxy-carbonylamino-4-(2,4,5-trifluorophenyl)butyric Acid by Asymmetric Reduction of Enamines [J]. Chinese Journal of Organic Chemistry, 2021, 41(5): 2105-2111.
[6]	Huaiyu Bin, Li Cheng, Xiaohui Yang, Jianhua Xie, Qilin Zhou. Enantioselective Construction of the Pyridine-Fused Chiral Bicyclo- [3.3.1]nonane Skeleton of Huperzine A and Its Analogues [J]. Chinese Journal of Organic Chemistry, 2021, 41(10): 4021-4027.
[7]	Liu Yuanhua, Dong Xiu-Qin, Zhang Xumu. Recent Advances of Nickel-Catalyzed Homogeneous Asymmetric Hydrogenation [J]. Chinese Journal of Organic Chemistry, 2020, 40(5): 1096-1104.
[8]	Gu Guoxian, Hu Yang, Liu Shaodong, Dong Xiu-Qin, Zhang Xumu. Indan-f-amphox: An Efficient PNN Ligand for Iridium-Catalyzed Asymmetric Hydrogenation of β-Aryl β-Ketoesters [J]. Chinese Journal of Organic Chemistry, 2020, 40(4): 997-1002.
[9]	Yang Xiaohui, Gu Xuesong, Bin Huaiyu, Xie Jianhua, Zhou Qilin. Asymmetric Synthesis of (-)-Indolizidine167B and (+)-Coniine [J]. Chinese Journal of Organic Chemistry, 2020, 40(11): 3963-3968.
[10]	Hong Mei, Min Jie, Wang Shifa. Research Progress of the Synthesis, Immobilization Bis(perfluoro-alkylsulfonyl)imide-Based Complexes and Application in Heterogeneous Catalysis [J]. Chin. J. Org. Chem., 2018, 38(8): 1907-1916.
[11]	Kong Shengnan, Malik Abaid Ullah, Qian Xuefeng, Shu Mouhai, Xiao Wende. Asymmetric Hydrogenation of β-Keto Esters Catalyzed by Ruthenium Species Supported on Porous Organic Polymer [J]. Chin. J. Org. Chem., 2018, 38(3): 656-664.
[12]	Chen Shuqi, Yang Wen, Yao Yongqi, Yang Xin, Deng Yingying, Yang Dingqiao. Progress in Ruthenium-Catalyzed Asymmetric Hydrogenation of β-Keto Esters [J]. Chin. J. Org. Chem., 2018, 38(10): 2534-2552.
[13]	Wang Zhihui, Zhang Zhenfeng, Liu Yangang, Zhang Wanbin. Development of the Asymmetric Hydrogenation of Enol Esters [J]. Chin. J. Org. Chem., 2016, 36(3): 447-459.
[14]	Han Yeqiang, Zhou Wenjie, Shen Haimin, Liu Qiuping, Yu Wenyan, Ji Hongbing, She Yuanbin. Progress in the Immobilization of β-Cyclodextrin and Their Application in Adsorption of Environmental Pollutants [J]. Chin. J. Org. Chem., 2016, 36(2): 248-257.
[15]	Yuan Qianjia, Zhang Wanbin. Applications of Phosphoramidite Ligands in Ir-Catalyzed Asymmetric Hydrogenation Reactions [J]. Chin. J. Org. Chem., 2016, 36(2): 274-282.