Citation: Liu Quanyao, Shi Lei, Liu Ning. Pyridine Bridged Organocatalyst for the Synthesis of 3-Aryl-2-oxazolidinones from Carbon Dioxide, Terminal Epoxide, and Aryl Amine[J]. Chinese Journal of Organic Chemistry, ;2019, 39(10): 2882-2891. doi: 10.6023/cjoc201903030 shu

Pyridine Bridged Organocatalyst for the Synthesis of 3-Aryl-2-oxazolidinones from Carbon Dioxide, Terminal Epoxide, and Aryl Amine

Key Laboratory for Green Processing of Chemical Engineering of Xinjiang Bingtuan, School of Chemistry and Chemical Engineering, Shihezi University, Shihezi 832003

Corresponding author: Liu Ning, ningliu@shzu.edu.cn
Received Date: 16 March 2018
Revised Date: 17 May 2019
Available Online: 3 October 2019

Figures(8)

A series of carboxyl group or hydroxyl group functionalized organocatalysts were synthesized and applied in three component reaction of carbon dioxide with epoxide, and aryl amines for the synthesis of 3-aryl-2-oxazolidinones. The method allows the reaction to proceed smoothly in the mild reaction conditions, together with excellent substrates scope of epoxides and aryl amines. The control experiments suggest that the cyclic carbonates are formed by the coupling of epoxides with carbon dioxide, which further react with the amino alcohol generated from epoxides and aryl amines, finally resulting in the desired products.
- organocatalyst,
- carbon dioxide,
- oxazolidinones,
- epoxide
1. [1]
  (a) Niemi, T.; Repo, T. Eur. J. Org. Chem. 2019, 1180.
  (b) Chellat, M. F.; Raguž, L.; Riedl, R. Angew. Chem., Int. Ed. 2016, 55, 6600.
  (c) Niemi, T.; Perea-Buceta, J. E.; Fernández, I.; Alakurtti, S.; Rantala, E.; Repo, T. Chem.-Eur. J. 2014, 20, 8867.
  (d) Dinsmore, C. J.; Mercer, S. P. Org. Lett. 2004, 6, 2885.
2. [2]
  (a) Chen, G.; Fu, C.; Ma, S. Org. Lett. 2009, 11, 2900.
  (b) Li, S.; Ye, J.; Yuan, W.; Ma, S. Tetrahedron 2013, 69, 10450.
3. [3]
  (a) Kayaki, Y.; Mori, N.; Ikariya, T. Tetrahedron Lett. 2009, 50, 6491.
  (b) Yamashita, K.; Hase, S.; Kayaki, Y.; Ikariya, T. Org. Lett. 2015, 17, 2334.
4. [4]
  (a) Wang, X.; Gao, W.-Y.; Niu, Z.; Wojtas, L.; Perman, J. A.; Chen, Y.-S.; Li, Z.; Aguila, B.; Ma, S. Chem. Commun. 2018, 54, 1170.
  (b) Dabral, S.; Schaub, T. Adv. Synth. Catal. 2019, 361, 223.
  (c) Adhikari, D.; Miller, A. W.; Baik, M.-H.; Nguyen, S. T. Chem. Sci. 2015, 6, 1293.
  (d) Liu, A.-H.; Dang, Y.-L.; Zhou, H.; Zhang, J.-J.; Lu, X.-B. ChemCatChem 2018, 10, 2686.
  (e) Seayad, J.; Seayad, A. M.; Ng, J. K. P.; Chai, C. L. L. ChemCatChem 2012, 4, 774.
  (f) Saptal, V. B.; Bhanage, B. M. ChemSusChem 2016, 9, 1980.
  (g) Liu, X.-F.; Wang, M.-Y.; He, L.-N. Curr. Org. Chem. 2017, 21, 698.
  (h) Phung, C.; Ulrich, R. M.; Ibrahim, M.; Tighe, N. T. G.; Lieberman, D. L.; Pinhas, A. R. Green Chem. 2011, 13, 3224.
  (i) Yang, Z.-Z.; Li, Y.-N.; Wei, Y.-Y.; He, L.-N. Green Chem. 2011, 13, 2351.
  (j) Chen, Y.; Luo, R.; Yang, Z.; Zhou, X.; Ji, H. Sustainable Energy Fuels 2018, 2, 125.
  (k) Kathalikkattil, A. C.; Tharun, J.; Roshan, R.; Soek, H.-G.; Park, D.-W. Appl. Catal., A 2012, 447-448, 107.
  (l) Zhao, Y.-N.; Yang, Z.-Z.; Luo, S.-H.; He, L.-N. Catal. Today 2013, 200, 2.
5. [5]
  (a) Ye, J.-H.; Song, L.; Zhou, W.-J.; Ju, T.; Yin, Z.-B.; Yan, S.-S.; Zhang, Z.; Li, J.; Yu, D.-G. Angew. Chem., Int. Ed. 2016, 55, 10022.
  (b) Wang, M.-Y.; Cao, Y.; Liu, X.; Wang, N.; He, L.-N.; Li, S.-H. Green Chem. 2017, 19, 1240.
  (c) Yin, Z.-B.; Ye, J.-H.; Zhou, W.-J.; Zhang, Y.-H.; Ding, L.; Gui, Y.-Y.; Yan, S.-S.; Li, J.; Yu, D.-G. Org. Lett. 2018, 20, 190.
  (d) Sun, L.; Ye, J.-H.; Zhou, W.-J.; Zeng, X.; Yu, D.-G. Org. Lett. 2018, 20, 3049.
  (e) Takeda, Y.; Okumura, S.; Tone, S.; Sasaki, I.; Minakata, S. Org. Lett. 2012, 14, 4874.
6. [6]
  (a) Peshkov, V. A.; Pereshivko, O. P.; Nechaev, A. A.; Peshkov, A. A.; Van der Eycken, E. V. Chem. Soc. Rev. 2018, 47, 3861.
  (b) Brunel, P.; Monot, J.; Kefalidis, C. E.; Maron, L.; Martin-Vaca, B.; Bourissou, D. ACS Catal. 2017, 7, 2652.
  (c) Chang, Z.; Jing, X.; He, C.; Liu, X.; Duan, C. ACS Catal. 2018, 8, 1384.
  (d) Zhao, Y.; Qiu, J.; Tian, L.; Li, Z.; Fan, M.; Wang, J. ACS Sustainable Chem. Eng. 2016, 4, 5553.
  (e) Hu, J.; Ma, J.; Zhu, Q.; Zhang, Z.; Wu, C.; Han, B. Angew. Chem., Int. Ed. 2015, 54, 5399.
  (f) García-Domínguez, P.; Fehr, L.; Rusconi, G.; Nevado, C. Chem. Sci. 2016, 7, 3914.
  (g) Liu, X.; Wang, M.-Y.; Wang, S.-Y.; Wang, Q.; He, L.-N. ChemSusChem 2017, 10, 1210.
  (h) Hu, J.; Ma, J.; Zhang, Z.; Zhu, Q.; Zhou, H.; Lu, W.; Han, B. Green Chem. 2015, 17, 1219.
  (i) Zhao, D.; Liu, X.-H.; Zhu, C.; Kang, Y.-S.; Wang, P.; Shi, Z.; Lu, Y.; Sun, W.-Y. ChemCatChem 2017, 9, 4598.
  (j) Yang, H.; Zhang, X.; Zhang, G.; Fei, H. Chem. Commun. 2018, 54, 4469.
7. [7]
  (a) Rintjema, J.; Epping, R.; Fiorani, G.; Martín, E.; Escudero-Adán, E. C.; Kleij, A. W. Angew. Chem., Int. Ed. 2016, 55, 3972.
  (b) Rintjema, J.; Guo, W.; Martin, E.; Escudero-Adán, E. C.; Kleij, A. W. Chem.-Eur. J. 2015, 21, 10754.
  (c) Lee, Y.; Choi, J.; Kim, H. Org. Lett. 2018, 20, 5036.
8. [8]
9. [9]
  (a) Niemi, T.; Perea-Buceta, J. E.; Fernández, I.; Hiltunen, O.-M.; Salo, V.; Rautiainen, S.; Räisänen, M. T.; Repo, T. Chem.-Eur. J. 2016, 22, 10355.
  (b) Mei, C.; Zhao, Y.; Chen, Q.; Cao, C.; Pang, G.; Shi, Y. ChemCatChem 2018, 10, 3057-3068.
10. [10]
  (a) Wang, B.; Yang, S.; Min, L.; Gu, Y.; Zhang, Y.; Wu, X.; Zhang, L.; Elageed, E. H. M.; Wu, S.; Gao, G. Adv. Synth. Catal. 2014, 356, 3125.
  (b) Zhang, L.; Fu, X.; Gao, G. ChemCatChem 2011, 3, 1359.
  (c) Selva, M.; Fabris, M.; Lucchini, V.; Perosa, A.; Noè, M. Org. Biomol. Chem. 2010, 8, 5187.
  (d) Lang, X.-D.; Li, Z.-M.; He, L.-N. Catal. Today 2019, 324, 167.
  (e) Hang, G.; Nian-Fa, Y.; Guo-Jun, D.; Guang-Yi, X. Chem. Lett. 2009, 38, 584.
  (f) Zhang, Y.; Wang, B.; Elageed, E. H. M.; Qin, L.; Ni, B.; Liu, X.; Gao, G. ACS Macro Lett. 2016, 5, 435.
11. [11]
  Wang, B.; Elageed, E. H. M.; Zhang, D.; Yang, S.; Wu, S.; Zhang, G.; Gao, G. ChemCatChem 2014, 6, 278. doi: 10.1002/cctc.201300801
12. [12]
  Hosseinian, A.; Ahmadi, S.; Mohammadi, R.; Monfared, A.; Rahmani, Z. J. CO2 Util. 2018, 27, 381. doi: 10.1016/j.jcou.2018.08.013
13. [13]
  Wang, B.; Luo, Z.; Elageed, E. H. M.; Wu, S.; Zhang, Y.; Wu, X.; Xia, F.; Zhang, G.; Gao, G. ChemCatChem 2016, 8, 830. doi: 10.1002/cctc.201500928
14. [14]
  Lv, M.; Wang, P.; Yuan, D.; Yao, Y. ChemCatChem 2017, 9, 4451. doi: 10.1002/cctc.201700594
15. [15]
  Seo, U. R.; Chung, Y. K. Green Chem. 2017, 19, 803. doi: 10.1039/C6GC02934E
16. [16]
  Sadeghzadeh, S. M.; Zhiani, R.; Emrani, S. Catal. Lett. 2018, 148, 119. doi: 10.1007/s10562-017-2217-z
17. [17]
  Xu, B.; Wang, P.; Lv, M.; Yuan, D.; Yao, Y. ChemCatChem 2016, 8, 2466. doi: 10.1002/cctc.201600534
18. [18]
  Chen, F.; Li, M.; Wang, J.; Dai, B.; Liu, N. J. CO₂ Util. 2018, 28, 181. doi: 10.1016/j.jcou.2018.09.025
19. [19]
  (a) Wang, L.; Liu, N.; Dai, B.; Hu, H. Eur. J. Org. Chem. 2014, 2014, 6493.
  (b) Liu, Q.-Y.; Shi, L.; Liu, N. J. Chem. Res. 2019, 43, 248.
20. [20]
  Wang, P.; Qin, J.; Yuan, D.; Wang, Y.; Yao, Y. ChemCatChem 2015, 7, 1145. doi: 10.1002/cctc.201403015
1. [1]
  Jiayi Yang , Jianxiu Hao , Huacong Zhou , Quansheng Liu . “Gorgeous Transformation” of Carbon Dioxide into Cyclic Carbonates: Catalyst Types and Roles. University Chemistry, 2026, 41(2): 178-189. doi: 10.12461/PKU.DXHX202502105
2. [2]
  Hailian Cheng , Shuaiqiang Jia , Chunjun Chen , Haihong Wu , Buxing Han . Electrocatalytic CO₂ Conversion: A Key to Unlocking a Low-Carbon Future. University Chemistry, 2026, 41(2): 1-13. doi: 10.12461/PKU.DXHX202502023
3. [3]
  Xiaolong Li , Shiqi Zhong , Xiangfeng Wei , Zhiqiang Liu , Pan Zhan , Jiehua Liu . Carbon Dioxide: From the Past to the Future. University Chemistry, 2026, 41(2): 242-247. doi: 10.12461/PKU.DXHX202503013
4. [4]
  Yanhui Guo , Li Wei , Zhonglin Wen , Chaorong Qi , Huanfeng Jiang . Recent Progress on Conversion of Carbon Dioxide into Carbamates. Acta Physico-Chimica Sinica, 2024, 40(4): 2307004-0. doi: 10.3866/PKU.WHXB202307004
5. [5]
  Xiaofei Liu , He Wang , Li Tao , Weimin Ren , Xiaobing Lu , Wenzhen Zhang . Electrocarboxylation of Benzylic Phosphates and Phosphinates with Carbon Dioxide. Acta Physico-Chimica Sinica, 2024, 40(9): 2307008-0. doi: 10.3866/PKU.WHXB202307008
6. [6]
  Jiayin Hu , Yafei Guo , Long Li , Tianlong Deng . Teaching Innovation of Salt-Water System Phase Diagrams under the “Dual Carbon” Background: Introducing the Pressurized CO₂ Carbonization Phase Equilibria. University Chemistry, 2025, 40(11): 31-36. doi: 10.12461/PKU.DXHX202412031
7. [7]
  Wenliang Wang , Weina Wang , Tian Sheng , Nan Wei , Sufan Wang , Tao Zhou . 过渡金属/氧化物催化CO₂加H₂还原生成甲醇的甲酸盐与甲酰基路径的前线轨道对称性分析. University Chemistry, 2026, 41(9): 405-411. doi: 10.12461/PKU.DXHX202508059
8. [8]
  Xiaomin Kang , Chuanbao Jiao . Application of Metal-Organic Frameworks in CO₂ Catalytic Conversion: Promoting “Double Carbon” Actions for a Beautiful China. University Chemistry, 2026, 41(2): 208-217. doi: 10.12461/PKU.DXHX202503011
9. [9]
  Yingying Yu , Hang Xu . 基于X-射线单晶衍射精准构筑簇基金属有机框架及其CO₂催化转化. University Chemistry, 2026, 41(10): 132-142. doi: 10.12461/PKU.DXHX202511033
10. [10]
  Honghong Zhang , Zhen Wei , Derek Hao , Lin Jing , Yuxi Liu , Hongxing Dai , Weiqin Wei , Jiguang Deng . 非均相催化CO₂与烃类协同催化转化的最新进展. Acta Physico-Chimica Sinica, 2025, 41(7): 100073-0. doi: 10.1016/j.actphy.2025.100073
11. [11]
  Yucai Zhang , Jun Jiang . Electrochemical Carbon Dioxide Reduction to Ethylene. University Chemistry, 2026, 41(2): 190-196. doi: 10.12461/PKU.DXHX202503006
12. [12]
  Zhiquan Zhang , Baker Rhimi , Zheyang Liu , Min Zhou , Guowei Deng , Wei Wei , Liang Mao , Huaming Li , Zhifeng Jiang . Insights into the Development of Copper-Based Photocatalysts for CO₂ Conversion. Acta Physico-Chimica Sinica, 2024, 40(12): 2406029-0. doi: 10.3866/PKU.WHXB202406029
13. [13]
  Tianhao GE , Sirong LU , Zhiyin XIAO , Wei ZHONG . Synthesis of porphyrin-based ionic polymeric materials for catalytic application in CO₂ conversion. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 722-736. doi: 10.11862/CJIC.20250312
14. [14]
  Yan Kong , Wei Wei , Lekai Xu , Chen Chen . Electrochemical Synthesis of Organonitrogen Compounds from N-integrated CO₂ Reduction Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2307049-0. doi: 10.3866/PKU.WHXB202307049
15. [15]
  Bizhu Shao , Huijun Dong , Yunnan Gong , Jianhua Mei , Fengshi Cai , Jinbiao Liu , Dichang Zhong , Tongbu Lu . Metal-Organic Framework-Derived Nickel Nanoparticles for Efficient CO₂ Electroreduction in Wide Potential Windows. Acta Physico-Chimica Sinica, 2024, 40(4): 2305026-0. doi: 10.3866/PKU.WHXB202305026
16. [16]
  Qiang Zhang , Yuanbiao Huang , Rong Cao . Imidazolium-Based Materials for CO₂ Electroreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306040-0. doi: 10.3866/PKU.WHXB202306040
17. [17]
  Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201
18. [18]
  Jianan Hong , Chenyu Xu , Yan Liu , Changqi Li , Menglin Wang , Yanwei Zhang . Decoding the interfacial competition between hydrogen evolution and CO₂ reduction via edge-active-site modulation in photothermal catalysis. Acta Physico-Chimica Sinica, 2025, 41(9): 100099-0. doi: 10.1016/j.actphy.2025.100099
19. [19]
  Hui-Ying Chen , Hao-Lin Zhu , Pei-Qin Liao , Xiao-Ming Chen . Integration of Ru(Ⅱ)-Bipyridyl and Zinc(Ⅱ)-Porphyrin Moieties in a Metal-Organic Framework for Efficient Overall CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(4): 2306046-0. doi: 10.3866/PKU.WHXB202306046
20. [20]
  Jie ZHAO , Huili ZHANG , Xiaoqing LU , Zhaojie WANG . Theoretical calculations of CO₂ capture and separation by functional groups modified 2D covalent organic framework. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 275-283. doi: 10.11862/CJIC.20240213

Get Citation

PDF

XML

Metrics

PDF Downloads(16)
Abstract views(2742)
HTML views(288)

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