Skip to main content

Porous nitrogen-doped carbon supported MoO2/Mo2C hybrid catalyst for efficient oxidative coupling of primary amines to imines

Journal of Porous Materials (2022)Cite this article

Abstract

A MoO2/Mo2C hybrid catalyst supported on N-doped carbon (Mo2C/MoO2@NC) was successfully prepared, which is featured with moderate mesoporosity, uniform metallic nanoparticles, and rich oxygen-vacancies. It showed excellent efficiency (99% imine yield) and good reusability for oxidative self-coupling of benzylamine to N-benzylbenzaldimine under mild conditions (85 °C, 3 h, 1 bar O2). In addition, the catalyst Mo2C/MoO2@NC also exhibited a universal applicability for oxidative coupling of other primary amines to imines with impressive conversion and satisfying target product selectivity. This method provides an efficient and environment friendly strategy for catalytic synthesis of complex imines from primary amines.

This is a preview of subscription content, access via your institution.

Access options

Buy single article

Instant access to the full article PDF.

USD 39.95

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

References

  1. J.G. Chen, Chem. Rev. 96(4), 1477–1498 (1996)

    Article  CAS  PubMed  Google Scholar 

  2. N. Ji, T. Zhang, M. Zheng, A. Wang, H. Wang, X. Wang, J.G. Chen, Angew. Chem. Int. Ed. 47(44), 8510–8513 (2008)

    Article  CAS  Google Scholar 

  3. Q. Gao, W. Zhang, Z. Shi, L. Yang, Y. Tang, Adv. Mater. 31(2), 1802880 (2019)

    Article  Google Scholar 

  4. Z. Li, C. Chen, E. Zhan, N. Ta, Y. Li, W. Shen, Chem. Commun. 50(34), 4469–4471 (2014)

    Article  CAS  Google Scholar 

  5. E. Gomez, B. Yan, S. Kattel, J.G. Chen, Nat. Rev. Chem. 3(11), 638–649 (2019)

    Article  CAS  Google Scholar 

  6. H. Sun, G. Li, J. Luo, M. Rao, Z. Peng, T. Jiang, Mater. Des. 193, 108803 (2020)

    Article  CAS  Google Scholar 

  7. F.E. Kühn, A.M. Santos, M. Abrantes, Chem. Rev. 106(6), 2455–2475 (2006)

    Article  PubMed  Google Scholar 

  8. Y. Zhou, Y. Chai, X. Li, Z. Wu, J. Lin, Y. Han, L. Li, H. Qi, Y. Gu, L. Kang, X. Wang, ACS Catal. 11(24), 15223–15233 (2021)

    Article  CAS  Google Scholar 

  9. R. Jana, C. Chowdhury, S. Malik, A. Datta, ACS Appl. Energy Mater. 2(8), 5613–5621 (2019)

    Article  CAS  Google Scholar 

  10. X. Huang, G. Lu, K. Zhang, J. Liu, H. Zhang, Z. Guo, J. Tao, Appl. Surf. Sci. 514, 145948 (2020)

    Article  CAS  Google Scholar 

  11. J. Xu, C. Zhang, H. Liu, J. Sun, R. Xie, Y. Qiu, F. Lü, Y. Liu, L. Zhuo, X. Liu, J. Luo, Nano Energy 70, 104529 (2020)

    Article  CAS  Google Scholar 

  12. X. Li, J. Yu, J. Jia, A. Wang, L. Zhao, T. Xiong, H. Liu, W. Zhou, Nano Energy 62, 127–135 (2019)

    Article  Google Scholar 

  13. B. Govinda Rao, P. Sudarsanam, A. Rangaswamy, B.M. Reddy, Catal. Lett. 145(7), 1436–1445 (2015)

    Article  CAS  Google Scholar 

  14. H. Tian, X. Cui, L. Zeng, L. Su, Y. Song, J. Shi, J. Mater. Chem. A 7(11), 6285–6293 (2019)

    Article  CAS  Google Scholar 

  15. C.P. Dong, Y. Higashiura, K. Marui, S. Kumazawa, A. Nomoto, M. Ueshima, A. Ogawa, ACS Omega 1(5), 799–807 (2016)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  16. L. Peng, H.G. Baldovi, A. Dhakshinamoorthy, A. Primo, H. Garcia, ACS Omega 7(13), 11092–11100 (2022)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. J.C. Espinosa, M. Álvaro, A. Dhakshinamoorthy, S. Navalón, H. García, ACS Sustain. Chem. Eng. 7(19), 15948–15956 (2019)

    Article  CAS  Google Scholar 

  18. H. Ji, T. Fei, L. Zhang, J. Yan, Y. Fan, J. Huang, Y. Song, Y. Man, H. Tang, H. Xu, H. Li, Appl. Surf. Sci. 457, 1142–1150 (2018)

    Article  CAS  Google Scholar 

  19. X. Liu, Y. Zhou, C.L. Wang, Y. Liu, D.J. Tao, Chem. Eng. J. 427, 130878 (2022)

    Article  CAS  Google Scholar 

  20. H. Yan, Y. Xie, Y. Jiao, A. Wu, C. Tian, X. Zhang, L. Wang, H. Fu, Adv. Mater. 30(2), 1704156 (2018)

    Article  Google Scholar 

  21. P. Phalswal, P.K. Khanna, Mater. Lett. 302, 130445 (2021)

    Article  CAS  Google Scholar 

  22. J. Jia, T. Xiong, L. Zhao, F. Wang, H. Liu, R. Hu, J. Zhou, W. Zhou, S. Chen, ACS Nano 11(12), 12509–12518 (2017)

    Article  CAS  PubMed  Google Scholar 

  23. X. Zhao, Y. Zhou, K. Huang, C. Li, D.J. Tao, ACS Sustainable Chem. Eng. 7(2), 1901–1908 (2018)

    Article  Google Scholar 

  24. X. Tang, B. Zhang, Y. Li, Y. Xu, Q. Xin, W. Shen, Catal. Lett. 97(3), 163–169 (2004)

    Article  CAS  Google Scholar 

  25. W. Cui, N. Cheng, Q. Liu, C. Ge, A.M. Asiri, X. Sun, ACS Catal. 4(8), 2658–2661 (2014)

    Article  CAS  Google Scholar 

  26. L. Ma, P. Chen, G. Zhang, L. Wang, F. Tang, X. Zhao, J. Wang, J. Huang, Y.-N. Liu, ChemCatChem 13(14), 3283–3289 (2021)

    Article  CAS  Google Scholar 

  27. X. Zhao, Y. Zhou, A.L. Jin, K. Huang, F. Liu, D.J. Tao, New J. Chem. 42(19), 15871–15878 (2018)

    Article  CAS  Google Scholar 

  28. T. Li, J. He, B. Peña, C.P. Berlinguette, Angew. Chem. Int. Ed. 55(5), 1769–1772 (2016)

    Article  CAS  Google Scholar 

  29. Q. Zhang, X. Zhao, L. Duan, H. Shen, R. Liu, T. Hou, CrystEngComm 22(31), 5245–5254 (2020)

    Article  CAS  Google Scholar 

  30. X.H. Li, M. Antonietti, Angew. Chem. Int. Ed. Engl. 52(17), 4572–4576 (2013)

    Article  CAS  PubMed  Google Scholar 

  31. C. Wu, J. Bu, W. Wang, H. Shen, Y. Cao, H. Zhang, Ind. Eng. Chem. Res. 61(16), 5442–5452 (2022)

    Article  CAS  Google Scholar 

  32. Q. Xu, B. Feng, C. Ye, Y. Fu, D.-L. Chen, F. Zhang, J. Zhang, W. Zhu, A.C.S. Appl, Mater. Interfaces 13(13), 15168–15177 (2021)

    Article  CAS  Google Scholar 

  33. S. Shubhashish, H.S. Khanna, L.A. Achola, A.S. Amin, W.S. Willis, S.L. Suib, A.C.S. Appl, Nano Mater. 4(2), 2086–2097 (2021)

    CAS  Google Scholar 

  34. C.K.P. Neeli, S. Ganji, V.S.P. Ganjala, S.R.R. Kamaraju, D.R. Burri, RSC Adv. 4(27), 14128–14135 (2014)

    Article  CAS  Google Scholar 

  35. M. Gopiraman, I.M. Chung, J. Taiwan. Inst. Chem. E. 81, 455–464 (2017)

    Article  CAS  Google Scholar 

  36. J. Xu, J. Li, K. Yang, H. Li, J. Inorg. Organomet. 30(4), 1384–1392 (2020)

    Article  CAS  Google Scholar 

Download references

Funding

This work was supported by the National Natural Science Foundations of China (22068013), the Key Research and Development Program of Jiangxi Province (20202BBGL73118), and the Key Lab of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education, Jiangxi Normal University (KFSEMC-202209). W.T.C. was supported by the Scientific Research Foundation of graduate innovation of Jiangxi Province Education Department (YC2021-B064).

Author information

Authors and Affiliations

  1. National Engineering Research Center for Carbohydrate Synthesis, Key Laboratory of Fluorine and Silicon for Energy Materials and Chemistry of Ministry of Education, College of Chemistry and Chemical Engineering, Jiangxi Normal University, Nanchang, 330022, China

    Wen-Ting Chen, Song Han, Zhi-Hong Dai, Yu-Xuan Fu, Ming-Shuai Sun, Zhang-Min Li, Yan Zhou & Duan-Jian Tao

  2. School of Chemical Engineering, Guizhou Institute of Technology, Guiyang, 550003, China

    Wen-Ting Chen

Authors
  1. Wen-Ting Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Song Han
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zhi-Hong Dai
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yu-Xuan Fu
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Ming-Shuai Sun
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Zhang-Min Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yan Zhou
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Duan-Jian Tao
    View author publications

    You can also search for this author in PubMed Google Scholar

Contributions

W-TC: Investigation, Writing-original draft, Data curation. SH: Methodology, Investigation. Z-HD: Methodology, Investigation. Y-XF: Methodology, Investigation. M-SS: Methodology, Investigation, Writing-review & editing. Z-ML: Funding acquisition, Methodology, Writing-review & editing. YZ: Supervision, Conceptualization, Resources, Writing-review & editing. D-JT: Supervision, Conceptualization, Funding acquisition, Resources, Writing-review & editing.

Corresponding authors

Correspondence to Yan Zhou or Duan-Jian Tao.

Ethics declarations

Competing interests

The authors declare no Competing interests.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 2220 KB)

Rights and permissions

Springer Nature or its licensor (e.g. a society or other partner) holds exclusive rights to this article under a publishing agreement with the author(s) or other rightsholder(s); author self-archiving of the accepted manuscript version of this article is solely governed by the terms of such publishing agreement and applicable law.

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Chen, WT., Han, S., Dai, ZH. et al. Porous nitrogen-doped carbon supported MoO2/Mo2C hybrid catalyst for efficient oxidative coupling of primary amines to imines. J Porous Mater (2022). https://doi.org/10.1007/s10934-022-01375-2

Download citation

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s10934-022-01375-2

Keywords

  • Amines
  • Imines
  • Oxidative self-coupling
  • Molybdenum carbide
  • Oxygen vacancy