ARTICLES

Synthesis of β-Oxopropylcarbamates Catalyzed by ZnO/Ionic Liquids under Atmospheric CO2

  • Yong Xu ,
  • Yongxing Zhang ,
  • Jia Hu ,
  • Cheng Chen ,
  • Ye Yuan ,
  • Francis Verpoort
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  • a State Key Laboratory of Advanced Technology for Materials Synthesis and Processing, Wuhan University of Technology, Wuhan 430070
    b School of Material Science and Engineering, Wuhan University of Technology, Wuhan 430070
These authors contributed equally to this work.

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)

Abstract

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.

Cite this article

Yong Xu , Yongxing Zhang , Jia Hu , Cheng Chen , Ye Yuan , Francis Verpoort . Synthesis of β-Oxopropylcarbamates Catalyzed by ZnO/Ionic Liquids under Atmospheric CO2[J]. Chinese Journal of Organic Chemistry, 2022 , 42(8) : 2542 -2550 . DOI: 10.6023/cjoc202201015

References

[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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