Skip to main content
Log in

Nitrogen Doped Carbon–Silica Based Cu(0) Nanometal Catalyst Enriched with Well-Defined N-moieties: Synthesis and Application in One-Pot Synthesis of 1,4-Disubstituted-1,2,3-triazoles

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

A novel, air stable, water dispersible and efficient catalyst based on copper nanoparticles immobilized on nitrogen doped carbons derived from inorganic–organic composite [Cu(0)@NDC-Sil] has been prepared. Doping of carbons i.e. inorganic–organic (silica–starch) composite using 5-phenyl-1,2,3,4-tetrazole, a nitrogen-rich precursor imparts a variety of nitrogen functionalities even at moderate temperature and enables the generation of active sites for the immobilization of Cu(0) nanoparticles. The novel catalyst system has been well characterized by various techniques like SEM, HRTEM, STEM, TGA, CHN, EDX, ICP-AES, XRD and XPS and was found to be highly efficient for the one-pot synthesis of 1,4-disubstituted-1,2,3-triazoles via click chemistry approach with a wide range of substrate scope such as benzyl/allyl halides and alkyl bromides. Moreover, it could be easily recovered by filtration and reused without significant loss in its activity.

Graphic Abstract

This is a preview of subscription content, log in via an institution to check access.

Access this article

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

Instant access to the full article PDF.

Institutional subscriptions

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

Similar content being viewed by others

References

  1. Deng Y, Xie Y, Zou K, Ji X (2016) J Mater Chem A 4:1144

    CAS  Google Scholar 

  2. Li XL, Wang HL, Robinson JT, Sanchez H, Diankov G, Dai HJ (2009) J Am Chem Soc 131:15939

    CAS  PubMed  Google Scholar 

  3. Lin ZY, Waller G, Liu Y, Liu ML, Wong CP (2012) Adv Energy Mater 2:884

    CAS  Google Scholar 

  4. Sheng ZH, Shao L, Chen JJ, Bao WJ, Wang FB, Xia XH (2011) ACS Nano 5:4350

    CAS  PubMed  Google Scholar 

  5. Hou SC, Cai X, Wu HW, Yu X, Peng M, Yan K, Zou DC (2013) Energy Environ Sci 6:3356

    CAS  Google Scholar 

  6. Choi CH, Chung MW, Park SH, Woo SI (2013) RSC Adv 3:4246

    CAS  Google Scholar 

  7. Mao Y, Duan H, Xu B, Zhang L, Hu Y, Zhao C, Wang Z, Chen L, Yang Y (2012) Energy Environ Sci 5:7950

    CAS  Google Scholar 

  8. Li R, Cao A, Zhang Y, Li G, Jiang F, Li S, Chen D, Wang C, Ge J, Shu C (2014) ACS Appl Mater Interfaces 6:20574

    CAS  PubMed  Google Scholar 

  9. Liu D, Chen X, Xu G, Guan J, Cao Q, Dong B, Qi Y, Li C, Mu X (2016) Sci Rep 6:21365

    PubMed  PubMed Central  Google Scholar 

  10. Agalave SG, Maujan SR, Pore VS (2011) Chem Asian J 6:2696

    CAS  PubMed  Google Scholar 

  11. Amini M, Hassandoost R, Bagherzadeh M, Gautam S, Chae KH (2016) Catal Commun 85:13

    CAS  Google Scholar 

  12. Haldon E, Nicasio MC, Perez PJ (2015) Org Biomol Chem 13:9528

    CAS  PubMed  Google Scholar 

  13. Chanda K, Rej S, Huang MH (2013) Chem Eur J 19:16036

    CAS  PubMed  Google Scholar 

  14. Tsai Y-H, Chanda K, Chu Y-T, Chiu C-Y, Huang MH (2014) Nanoscale 6:8704

    CAS  PubMed  Google Scholar 

  15. Rej S, Chanda K, Chiu C-Y, Huang MH (2014) Chem Eur J 20:15991

    CAS  PubMed  Google Scholar 

  16. Madasu M, Hsia C-F, Huang MH (2017) Nanoscale 9:6970

    CAS  PubMed  Google Scholar 

  17. Beneteau V, Olmos A, Boningari T, Sommer J, Pale P (2010) Tetrahedron Lett 51:3673

    CAS  Google Scholar 

  18. El-bendary MM, Saleh TS, Al-Bogami AS (2018) Catal Lett 148:3797

    CAS  Google Scholar 

  19. Nasrollahzadeh M, Jaleh B, Fakhri P, Zahraei A, Ghadery E (2015) RSC Adv 5:2785

    CAS  Google Scholar 

  20. Mishra A, Rai P, Srivastava M, Tripathi BP, Yadav S, Singh J, Singh J (2017) Catal Lett 147:2600

    CAS  Google Scholar 

  21. Bihani M, Pasupuleti BG, Bora PP, Bez G, Lal RA (2018) Catal Lett 148:1315

    CAS  Google Scholar 

  22. Yu WB, Jiang LX, Shen C, Xu WM, Zhang PF (2016) Catal Commun 79:11

    CAS  Google Scholar 

  23. Wan L, Cai C (2012) Catal Lett 142:1134

    CAS  Google Scholar 

  24. Salamatmanesh A, Miraki MK, Yazdani E, Heydari A (2018) Catal Lett 148:3257

    CAS  Google Scholar 

  25. Jahanshahia R, Akhlaghinia B (2016) RSC Adv 6:29210

    Google Scholar 

  26. Sharma H, Mahajan H, Jamwal B, Paul S (2018) Catal Commun 107:68

    CAS  Google Scholar 

  27. Bhardwaj M, Kour M, Paul S (2016) RSC Adv 6:99604

    CAS  Google Scholar 

  28. Demko PZ, Sharpless KB (2001) J Org Chem 66:7945

    CAS  PubMed  Google Scholar 

  29. Han X, He X, Sun L, Han X, Zhan W, Xu J, Wang X, Chen J (2018) ACS Catal 8:3348

    Google Scholar 

  30. Qian Y, Du P, Wu P, Cai C, Gervasio DF (2016) J Phys Chem C 120:9884

    CAS  Google Scholar 

  31. Blonski P, Tucek J, Sofer Z, Mazanek V, Petr M, Pumera M, Otyepka M, Zboril R (2017) J Am Chem Soc 139:3171

    CAS  PubMed  PubMed Central  Google Scholar 

  32. Eisenberg D, Slot TK, Rothenberg G (2018) ACS Catal 8:8618

    CAS  Google Scholar 

  33. Fiorio JL, Gonçalves RV, Teixeira-Neto E, Ortuno MA, Lopez N, Rossi LM (2018) ACS Catal 8:3516

    CAS  Google Scholar 

  34. Zhang R, Sun Z, Feng R, Lin Z, Liu H, Li M, Yang Y, Shi R, Zhang W, Chen Q (2017) ACS Appl Mater Interfaces 9:38419

    CAS  PubMed  Google Scholar 

  35. Sahraie NR, Paraknowitsch JP, Gobel G, Thomas A, Strasser P (2014) J Am Chem Soc 136:14486

    Google Scholar 

  36. Zheng L, Zheng S, Wei H, Du L, Zhu Z, Chen J, Yang D (2019) ACS Appl Mater Interfaces 11:6248

    CAS  PubMed  Google Scholar 

  37. Zhou W, Xiong T, Shi C, Zhou J, Zhou K, Zhu N, Li L, Tang Z, Chen S (2016) Angew Chemie Int Ed 128:8556

    Google Scholar 

  38. Hu Y, Zhang H, Wu P, Zhang H, Zhou B, Cai C (2011) Phys Chem Chem Phys 13:4083

    CAS  PubMed  Google Scholar 

  39. Kumar BSPA, Reddy KHV, Madhav B, Ramesh K, Nageswar YVD (2012) Tetrahedron Lett 53:4595

    Google Scholar 

  40. Vantikommu J, Palle S, Reddy PS, Ramanatham V, Khagga M, Pallapothula VR (2010) Eur J Med Chem 45:5044

    CAS  PubMed  Google Scholar 

  41. Albadi J, Keshavarz M, Shirini F, Vafaie-nezhad M (2012) Catal Commun 27:17

    CAS  Google Scholar 

Download references

Acknowledgements

We thank the Head, ACMS, IIT Kanpur for XPS study; Head, SAIF, IIT Bombay for ICP-AES, HR-TEM, STEM and CHN studies; AMRC, IIT Mandi for SEM, EDX and PXRD studies. Financial assistance to authors [CS (JRF, UGC) and MK (JRF, CSIR)] is gratefully acknowledged.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Satya Paul.

Additional information

Publisher's Note

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

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOC 2506 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sharma, C., Kaur, M., Choudhary, A. et al. Nitrogen Doped Carbon–Silica Based Cu(0) Nanometal Catalyst Enriched with Well-Defined N-moieties: Synthesis and Application in One-Pot Synthesis of 1,4-Disubstituted-1,2,3-triazoles. Catal Lett 150, 82–94 (2020). https://doi.org/10.1007/s10562-019-02936-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-019-02936-y

Keywords

Navigation