ZnO/离子液体体系催化常压二氧化碳合成β-羰基氨基甲酸酯
收稿日期: 2022-01-11
修回日期: 2022-04-02
网络出版日期: 2022-04-29
基金资助
国家自然科学基金(22102127); 国家自然科学基金(21950410754); 齐鲁工业大学(山东省科学院)生物基材料与绿色造纸国家重点实验室开放基金(GZKF202023); 催化转化与能源材料化学教育部重点实验室暨催化材料科学湖北省重点实验室开放基金(CHCL19002)
Synthesis of β-Oxopropylcarbamates Catalyzed by ZnO/Ionic Liquids under Atmospheric CO2
Received date: 2022-01-11
Revised date: 2022-04-02
Online published: 2022-04-29
Supported by
National Natural Science Foundation of China(22102127); National Natural Science Foundation of China(21950410754); State Key Laboratory of Biobased Material and Green Papermaking, Qilu University of Technology, Shandong Academy of Sciences(GZKF202023); Key Laboratory of Catalysis and Energy Materials Chemistry of Ministry of Education ;Hubei Key Laboratory of Catalysis and Materials Science(CHCL19002)
徐勇 , 张永兴 , 胡佳 , 陈宬 , 原晔 , Francis Verpoort . ZnO/离子液体体系催化常压二氧化碳合成β-羰基氨基甲酸酯[J]. 有机化学, 2022 , 42(8) : 2542 -2550 . DOI: 10.6023/cjoc202201015
Carbamate compounds exhibit a broad applicable scope in medicine, pesticide, resin modification, fabric finishing and organic synthesis. A methodology using ZnO/ionic liquids as the catalyst for the three-component coupling reactions of carbon dioxide (CO2), secondary amines and propargylic alcohols to produce various β-oxopropylcarbamates was developed. This catalytic system exhibited robust recyclability and broad substrate scope. Moreover, it showed considerable catalytic activity under atmospheric CO2, indicating its potential in carbon capture and utilization processes.
| [1] | Mikkelsen, M.; Jørgensen, M.; Krebs, F. C. Energy Environ. Sci. 2010, 3, 43. |
| [2] | Kumar, A.; Singh, P.; Raizada, P.; Hussain, C. M. Sci. Total Environ. 2022, 806, 150349. |
| [3] | Kondratenko, E. V.; Mul, G.; Baltrusaitis, J.; Larrazábal, G. O.; Pérez-Ramírez, J. Energy Environ. Sci. 2013, 6, 3112. |
| [4] | Arshadi, S.; Vessally, E.; Hosseinian, A.; Soleimani-amiri, S.; Edjlali, L. J. CO2 Util. 2017, 21, 108. |
| [5] | Chaturvedi, D.; Chaturvedi, A. K.; Mishra, V. Curr. Org. Chem. 2012, 16, 1609. |
| [6] | Chen, K.; Li, H.; He, L. Chin. J. Org. Chem. 2020, 40, 2195. (in Chinese) |
| [6] | (陈凯宏, 李红茹, 何良年, 有机化学, 2020, 40, 2195.) |
| [7] | Chaturvedi, D. Curr. Org. Chem. 2011, 15, 1593. |
| [8] | Chuqiang, Q.; Ning, C.; Jiaxi, X. Prog. Chem. 2018, 30, 139. (in Chinese) |
| [8] | (阙楚强, 陈宁, 许家喜, 化学进展, 2018, 30, 139.) |
| [9] | Matosevic, A.; Bosak, A. Arh. Hig. Rada Toksikol. 2020, 71, 285. |
| [10] | Loscher, W.; Sills, G. J.; White, H. S. Epilepsia 2021, 62, 596. |
| [11] | Chaturvedi, D.; Ray, S. Mon. Chem. 2006, 137, 127. |
| [12] | Schilling, W.; Das, S. ChemSusChem 2020, 13, 6246. |
| [13] | Niemi, T.; Repo, T. Eur. J. Inorg. Chem. 2019, 1180. |
| [14] | Hosseinian, A.; Ahmadi, S.; Mohammadi, R.; Monfared, A.; Rahmani, Z. J. CO2 Util. 2018, 27, 381. |
| [15] | Bruneau, C.; Dixncuf, P. H. Tetrahedron Lett. 1987, 28, 2005. |
| [16] | Sasaki, Y.; Dixneuf, P. H. J. Org. Chem. 1987, 52, 4389. |
| [17] | Kim, T.-J.; Kwon, K.-H.; Kwon, S.-C.; Baeg, J.-O.; Shim, S.-C.; Lee, D.-H. J. Organomet. Chem. 1990, 389, 205. |
| [18] | Asadi Zeydabadi, H.; Mehrzad, J.; Motavalizadehkakhky, A.; Zhiani, R. Catal. Lett. 2020, 151, 582. |
| [19] | Song, Q.-W.; Yu, B.; Li, X.-D.; Ma, R.; Diao, Z.-F.; Li, R.-G.; Li, W.; He, L.-N. Green Chem. 2014, 16, 1633. |
| [20] | Song, Q. W.; Chen, W. Q.; Ma, R.; Yu, A.; Li, Q. Y.; Chang, Y.; He, L. N. ChemSusChem 2015, 8, 821. |
| [21] | Wang, Q.; Xiong, W.; Deng, X.; Zhou, X.; Qi, C.; Hu, J. Asian J. Org. Chem. 2018, 8, 179. |
| [22] | Zhao, Q.-N.; Song, Q.-W.; Liu, P.; Zhang, K.; Hao, J. ChemistrySelect 2018, 3, 6897. |
| [23] | Song, Q.-W.; Liu, P.; Han, L.-H.; Zhang, K.; He, L.-N. Chin. J. Chem. 2018, 36, 147. |
| [24] | Li, X.; Lang, X.; Song, Q.; Guo, Y.; He, L. Chin. J. Org. Chem. 2016, 36, 744. (in Chinese) |
| [24] | (李雪冬, 郎咸东, 宋清文, 郭亚坤, 何良年, 有机化学, 2016, 36, 744.) |
| [25] | Li, D.; Du, M. C.; Bu, C.; Chen, C.; Hu, J.; Zhang, Y. X.; Yuan, Y.; Verpoort, F. J. Mol. Catal. Chin. 2019, 33, 542. (in Chinese) |
| [25] | (李迪, 杜旻辰, 卜超, 陈宬, 胡佳, 张永兴, 原晔, 弗朗西斯, 分子催化, 2019, 33, 542.) |
| [26] | Ca, N. D.; Gabriele, B.; Ruffolo, G.; Veltri, L.; Zanetta, T.; Costa, M. Adv. Synth. Catal. 2011, 353, 133. |
| [27] | Chang, L.; Zhiani, R.; Sadeghzadeh, S. M. RSC Adv. 2019, 9, 16955. |
| [28] | Fan, L.; Wang, J.; Zhang, X.; Sadeghzadeh, S. M.; Zhiani, R.; Shahroudi, M.; Amarloo, F. Catal. Lett. 2019, 149, 3465. |
| [29] | Zhang, X.; Chen, K. H.; Zhou, Z. H.; He, L. N. ChemCatChem 2020, 12, 4825. |
| [30] | Shi, G.; Zhai, R.; Li, H.; Wang, C. Green Chem. 2021, 23, 592. |
| [31] | Zhou, H.; Chen, W.; Liu, J.-H.; Zhang, W.-Z.; Lu, X.-B. Green Chem. 2020, 22, 7832. |
| [32] | Bates, E. D.; Mayton, R. D.; Ntai, I.; Davis, J. H. J. Am. Chem. Soc. 2002, 124, 926. |
| [33] | Yang, Z.-Z.; Zhao, Y.-N.; He, L.-N. RSC Adv. 2011, 1, 545. |
| [34] | Fan, H.-H.; Wang, A.; Yang, S.-R.; Jiang, H.-F. Chin. J. Org. Chem. 2008, 28, 768. (in Chinese) |
| [34] | (范晖华, 王阿忠, 杨少容, 江焕峰, 有机化学, 2008, 28, 768.) |
| [35] | Song, D.; Li, D.; Xiao, X.; Cheng, C.; Chaemchuen, S.; Yuan, Y.; Verpoort, F.. J. CO2 Util. 2018, 27, 217. |
| [36] | Hu, J.; Ma, J.; Zhu, Q.; Qian, Q.; Han, H.; Mei, Q.; Han, B. Green Chem. 2016, 18, 382. |
| [37] | Prasad, D.; Patil, K. N.; Chaudhari, N. K.; Kim, H.; Nagaraja, B. M.; Jadhav, A. H. Catal. Rev. 2020, 22,1. |
| [38] | Liu, P.; Song, Q.-W.; Zhao, Q.-N.; Li, J.-Y.; Zhang, K. Synthesis 2018, 51, 739. |
| [39] | Min, Z.; Li, Z.; Wang, H.; Xuan, X.; Zhao, Y.; Wang, J. ACS Sustainable Chem. Eng. 2021, 9, 853. |
| [40] | Gurau, G.; Rodriguez, H.; Kelley, S. P.; Janiczek, P.; Kalb, R. S.; Rogers, R. D. Angew. Chem., Int. Ed. 2011, 50, 12024. |
| [41] | Song, Q. W.; Zhou, Z. H.; Yin, H.; He, L. N. ChemSusChem 2015, 8, 3967. |
| [42] | Cao, C. S.; Xia, S. M.; Song, Z. J.; Xu, H.; Shi, Y.; He, L. N.; Cheng, P.; Zhao, B. Angew. Chem., Int. Ed. 2020, 59, 8586. |
| [43] | Sugiishi, T.; Nakamura, H. J. Am. Chem. Soc. 2012, 134, 2504. |
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