Skip to main content
Log in

Synthesis and characterization of Cu-modified ox-g-C3N4 nanosheets as an electrode for green synthesis of phenyl Benzofuran derivatives via C–H functionalization to C–O and C–C bond formation with an electrochemical oxidation system

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

In this study, our primary objective was to synthesize and characterize a copper nanoparticle-modified oxidized graphite carbon nitride (ox-g-C3N4). This modified ox-g-C3N4 material was utilized as a reusable catalyst for the environmentally friendly production of benzofuran 4(a-j) derivatives through C–H activation using an electrochemical oxidation system. The desired derivatives were obtained by reacting 2-bromophenol 1(a-c) with ethynylbenzene 2(a-g) yielding high yields ranging from 89 to 94%. The modified Cu/ox-g-C3N4 nanocomposite was thoroughly examined. using different analytical techniques, including thermogravimetric analysis (TGA), energy-dispersive X-ray spectroscopy (EDS), scanning electron microscopy (SEM), IR Fourier-transform infrared spectroscopy (FT-IR), Brunauer–Emmett–Teller (BET) analysis, cyclic voltammetry (CV), and X-ray diffraction (XRD) spectroscopy, and ultraviolet (UV) spectroscopy. The comprehensive identification was conducted in a comparative manner, allowing for a thorough understanding of the nanocomposite's properties. By employing this nanocatalyst, we implement a greener synthesis approach that reduces the need for dangerous and toxic substances, while reducing waste generation by promoting reuse. The synthesized products in this research were subjected to characterization utilizing techniques such as melting point analysis, CHN analysis and 1HNMR spectroscopy. These analytical methods were utilized to confirm the identification and assess the purity of the benzofuran compounds synthesized 4(a-j).

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.

Fig. 1
Scheme 1
Scheme 2
Scheme 3
Scheme 4
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Fig. 10
Scheme 5
Fig. 11
Fig. 12

Similar content being viewed by others

References

  1. H. Khanam, Eur. J. Med. Chem. 97, 483 (2015)

    Article  CAS  PubMed  Google Scholar 

  2. Z. Xu, S. Zhao, Z. Lv, L. Feng, Y. Wang, F. Zhang, L. Bai, J. Deng, Eur. J. Med. Chem. 162, 266 (2019)

    Article  CAS  PubMed  Google Scholar 

  3. A. Skerjanec, Clin. Pharmacokinet. 45, 325 (2006)

    Article  CAS  PubMed  Google Scholar 

  4. D. Kozlowski, S. Budrejko, G.Y.H. Lip, D.P. Mikhailidis, J. Rysz, G. Raczak, M. Banach, Ann. Med. 44, 60 (2012)

    Article  CAS  PubMed  Google Scholar 

  5. K. Bezchlibnyk-Butler, I. Aleksic, S.H. Kennedy, J. Psychiatry Neurosci. 25, 241 (2000)

    CAS  PubMed  PubMed Central  Google Scholar 

  6. R.H. Howland, J. Psychosoc. Nurs. Ment. Health Serv. 49, 19 (2011)

    Article  PubMed  Google Scholar 

  7. F.A. de Wolff, T.V. Thomas, Clin. Pharmacokinet. 11, 62 (1986)

    Article  PubMed  Google Scholar 

  8. V.F. Azevedo, I.A. Kos, A.B. Vargas-Santos, G.R.C. da Pinheiro, E.S. dos Paiva, Adv. Rheumatol. 59, 37 (2019)

    Article  PubMed  Google Scholar 

  9. L. van Erven, M.J. Schalij, Heart 96, 1593 (2010)

    Article  PubMed  Google Scholar 

  10. N.L. Borja, K.L. Daniel, Clin. Ther. 28, 1540 (2006)

    Article  CAS  PubMed  Google Scholar 

  11. C.L. Linares, X. Decleves, J.M. Oppert, A. Basdevant, K. Clement, C. Bardin, J.M. Scherrmann, J.P. Lepine, J.F. Bergmann, S. Mouly, Clin. Pharmacokinet. 48, 635 (2009)

    Article  CAS  Google Scholar 

  12. R. Patil, M. Mohan, V. Kasture, S. Kasture, Adv. Tradit. Med. 9, 1 (2009)

    Google Scholar 

  13. J. Tack, Expert Rev. Gastroenterol. Hepatol. 3, 337 (2009)

    Article  CAS  PubMed  Google Scholar 

  14. J. Kaur, I. Melkani, A.P. Singh, A.P. Singh, K. Bala, J. Drug Deliv. Ther. 12, 167 (2022)

    Article  CAS  Google Scholar 

  15. A. Firdaws, Al-Kitab J. Pure Sci. 7, 42 (2023)

    Article  Google Scholar 

  16. J. Liu, X. Xiao, Y. Lai, Z. Zhang, Org. Chem. Front. 9, 2256 (2022)

    Article  CAS  Google Scholar 

  17. S. Meng, W. Li, Z. Li, H. Song, Fuel 353, 129169 (2023)

    Article  CAS  Google Scholar 

  18. Y. Wen, J. Yan, B. Yang, Z. Zhuang, Y. Yu, J. Mater. Chem. A 10, 19184 (2022)

    Article  CAS  Google Scholar 

  19. H. Yang, Y. Dang, X. Cui, X. Bu, J. Li, S. Li, Y. Sun, P. Gao, Appl. Catal. B Environ. 321, 122050 (2023)

    Article  CAS  Google Scholar 

  20. B. Lou, N. Shakoor, M. Adeel, P. Zhang, L. Huang, Y. Zhao, W. Zhao, Y. Jiang, Y. Rui, J. Clean. Prod. 363, 132523 (2022)

    Article  CAS  Google Scholar 

  21. M. Tricoire, D. Wang, T. Rajeshkumar, L. Maron, G. Danoun, G. Nocton, JACS Au 2, 1881 (2022)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  22. Z.B. Shifrina, V.G. Matveeva, L.M. Bronstein, Chem. Rev. 120, 1350 (2019)

    Article  PubMed  Google Scholar 

  23. C.C. James, B. de Bruin, J.N.H. Reek, Angew. Chem. Int. Ed. 62, e202306645 (2023)

    Article  CAS  Google Scholar 

  24. L. Piccirilli, D.L.J. Pinheiro, M. Nielsen, Catalysts 10, 773 (2020)

    Article  CAS  Google Scholar 

  25. M. Sajid, Curr. Opin. Environ. Sci. Heal. 25, 100319 (2022)

    Article  Google Scholar 

  26. C.A. Malapit, M.B. Prater, J.R. Cabrera-Pardo, M. Li, T.D. Pham, T.P. McFadden, S. Blank, S.D. Minteer, Chem. Rev. 122, 3180 (2021)

    Article  PubMed  PubMed Central  Google Scholar 

  27. T. Kropp, M. Mavrikakis, ACS Catal. 9, 6864 (2019)

    Article  CAS  Google Scholar 

  28. J. Rakhtshah, Coord. Chem. Rev. 467, 214614 (2022)

    Article  CAS  Google Scholar 

  29. A.F. Baye, R. Appiah-Ntiamoah, H. Kim, Sci. Total. Environ. 712, 135492 (2020)

    Article  CAS  PubMed  Google Scholar 

  30. I.N. Reddy, L.V. Reddy, N. Jayashree, C.V. Reddy, M. Cho, D. Kim, J. Shim, Chemosphere 264, 128593 (2021)

    Article  CAS  PubMed  Google Scholar 

  31. W. Yu, L. Sisi, Y. Haiyan, L. Jie, RSC Adv. 10, 15328 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  32. M.D. Nguyen, H.-V. Tran, S. Xu, T.R. Lee, Appl. Sci. 11, 11301 (2021)

    Article  CAS  PubMed  Google Scholar 

  33. N. Rono, J.K. Kibet, B.S. Martincigh, V.O. Nyamori, Crit. Rev. Solid State Mater. Sci. 46, 189 (2021)

    Article  CAS  Google Scholar 

  34. A.A. Yadav, S.-W. Kang, Y.M. Hunge, J. Mater. Sci. Mater. Electron. 32, 15577 (2021)

    Article  CAS  Google Scholar 

  35. L. Liu, L. Min, W. Zhang, Y. Wang, J. Mater. Chem. A 9, 27518 (2021)

    Article  CAS  Google Scholar 

  36. M. Golestanzadeh, H. Naeimi, RSC Adv. 9, 27560 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  37. O. Mohammadi, M. Golestanzadeh, M. Abdouss, New J. Chem. 41, 11471 (2017)

    Article  CAS  Google Scholar 

  38. L. Kong, J. Wang, F. Ma, M. Sun, J. Quan, Appl. Mater. Today 16, 388 (2019)

    Article  Google Scholar 

  39. R. Tang, K. Sun, F. Liu, S. Lu, H. Chen, J. Chen, Res. Chem. Intermed. 50, 973 (2024)

    Article  CAS  Google Scholar 

  40. X. Huang, W. Gu, Y. Ma, D. Liu, N. Ding, L. Zhou, J. Lei, L. Wang, J. Zhang, Res. Chem. Intermed. 46, 5133 (2020)

    Article  CAS  Google Scholar 

  41. Y. Li, X. Li, H. Zhang, Q. Xiang, Nanoscale Horiz. 5, 765 (2020)

    Article  CAS  PubMed  Google Scholar 

  42. Y. Luo, Y. Yan, S. Zheng, H. Xue, H. Pang, J. Mater. Chem. A 7, 901 (2019)

    Article  CAS  Google Scholar 

  43. Q. Zhang, X. Liu, M. Chaker, D. Ma, ACS Mater. Lett. 3, 663 (2021)

    Article  CAS  Google Scholar 

  44. B. Dam, B. Das, B.K. Patel, Green Chem. 25, 3374 (2023)

    Article  CAS  Google Scholar 

  45. M. Ismael, J. Alloys Compd. 846, 156446 (2020)

    Article  CAS  Google Scholar 

  46. P. Anastas, N. Eghbali, Chem. Soc. Rev. 39, 301 (2010)

    Article  CAS  PubMed  Google Scholar 

  47. J. Song, B. Han, Natl. Sci. Rev. 2, 255 (2015)

    Article  Google Scholar 

  48. J.C. Siu, N. Fu, S. Lin, Acc. Chem. Res. 53, 547 (2020)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  49. N. Sbei, T. Hardwick, N. Ahmed, A.C.S. Sustain, Chem. Eng. 9, 6148 (2021)

    CAS  Google Scholar 

  50. W. Zhou, L. Xie, J. Gao, R. Nazari, H. Zhao, X. Meng, F. Sun, G. Zhao, J. Ma, Chem. Eng. J. 410, 128368 (2021)

    Article  CAS  Google Scholar 

  51. E.O. Bortnikov, S.N. Semenov, Curr. Opin. Electrochem. 35, 101050 (2022)

    Article  CAS  Google Scholar 

  52. S. Imeni, A. Makarem, R. Javahershenas, Asian J. Org. Chem. 12, e202300303 (2023)

    Article  CAS  Google Scholar 

  53. C. Ma, P. Fang, T.-S. Mei, ACS Catal. 8, 7179 (2018)

    Article  CAS  Google Scholar 

  54. S. Zhang, R.C. Samanta, N. Sauermann, L. Ackermann, Chem. Eur. J. 24, 19166 (2018)

    Article  CAS  PubMed  Google Scholar 

  55. N. Sauermann, T.H. Meyer, C. Tian, L. Ackermann, J. Am. Chem. Soc. 139, 18452 (2017)

    Article  CAS  PubMed  Google Scholar 

  56. F. Xu, Y.-J. Li, C. Huang, H.-C. Xu, ACS Catal. 8, 3820 (2018)

    Article  CAS  Google Scholar 

  57. Y. Qiu, W. Kong, J. Struwe, N. Sauermann, T. Rogge, A. Scheremetjew, L. Ackermann, Angew. Chem. Int. Ed. 57, 5828 (2018)

    Article  CAS  Google Scholar 

  58. C. Tian, U. Dhawa, A. Scheremetjew, L. Ackermann, ACS Catal. 9, 7690 (2019)

    Article  CAS  Google Scholar 

  59. Z. Zhang, L. Zhang, Y. Cao, F. Li, G. Bai, G. Liu, Y. Yang, F. Mo, Org. Lett. 21, 762 (2019)

    Article  CAS  PubMed  Google Scholar 

  60. B. Huang, Z. Sun, G. Sun, eScience 2, 243 (2022)

    Article  Google Scholar 

  61. T. Hyodo, W. Sakata, T. Ueda, Y. Shimizu, ECS Sens. Plus 1, 13602 (2022)

    Article  CAS  Google Scholar 

  62. G. Sikri, R.S. Sawhney, J. Mol. Model. 29, 115 (2023)

    Article  CAS  PubMed  Google Scholar 

  63. H. Lu, Z. Ke, L. Feng, B. Liu, Chemosphere 329, 138710 (2023)

    Article  CAS  PubMed  Google Scholar 

  64. M. Safaei, M.M. Foroughi, N. Ebrahimpoor, S. Jahani, A. Omidi, M. Khatami, TrAC Trends Anal. Chem. 118, 401 (2019)

    Article  CAS  Google Scholar 

  65. P. Poizot, J. Gaubicher, S. Renault, L. Dubois, Y. Liang, Y. Yao, Chem. Rev. 120, 6490 (2020)

    Article  CAS  PubMed  Google Scholar 

  66. W. Liu, M. Li, G. Jiang, G. Li, J. Zhu, M. Xiao, Y. Zhu, R. Gao, A. Yu, M. Feng, Adv. Energy Mater. 10, 2001275 (2020)

    Article  CAS  Google Scholar 

  67. Z. Zhao, Y. Sun, F. Dong, Nanoscale 7, 15 (2015)

    Article  CAS  PubMed  Google Scholar 

  68. P. Choudhary, A. Bahuguna, A. Kumar, S.S. Dhankhar, C.M. Nagaraja, V. Krishnan, Green Chem. 22, 5084 (2020)

    Article  CAS  Google Scholar 

  69. J. Liu, T. Zhang, Z. Wang, G. Dawson, W. Chen, J. Mater. Chem. 21, 14398 (2011)

    Article  CAS  Google Scholar 

  70. X. Wang, K. Maeda, A. Thomas, K. Takanabe, G. Xin, J.M. Carlsson, K. Domen, M. Antonietti, Nat. Mater. 8, 76 (2009)

    Article  CAS  PubMed  Google Scholar 

  71. P.K. Mandali, D.K. Chand, Synthesis (Stuttg). 47, 1661 (2015)

    Article  CAS  Google Scholar 

  72. J. Cao, Z. Chen, S. Li, G. Zhu, Y. Yang, C. Wang, W. Chen, J. Wang, J. Zhang, L. Tang, European. J. Org. Chem. 2018, 2774 (2018)

    CAS  Google Scholar 

  73. J. Liu, W. Chen, Y. Ji, L. Wang, Adv. Synth. Catal. 354, 1585 (2012)

    Article  CAS  Google Scholar 

  74. C. Wen, C. Wu, R. Luo, Q. Li, F. Chen, Synthesis (Stuttg). 53, 3847 (2021)

    Article  CAS  Google Scholar 

  75. T. Dao-Huy, M. Haider, F. Glatz, M. Schnürch, M.D. Mihovilovic, Eur. J. Org. Chem. 2014, 8119 (2014)

    Article  CAS  Google Scholar 

  76. M.A. Ranjbari, H. Tavakol, J. Org. Chem. 86, 4756 (2021)

    Article  CAS  PubMed  Google Scholar 

  77. I. Chakrabarty, M.O. Akram, S. Biswas, N.T. Patil, Chem. Commun. 54, 7223 (2018)

    Article  CAS  Google Scholar 

  78. M. Begala, P. Caboni, M.J. Matos, G.L. Delogu, Tetrahedron Lett. 59, 1711 (2018)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors extend their appreciation to the Researchers Supporting Project (RSPD2024R758), King Saud University, Riyadh, Saudi Arabia.

Author information

Authors and Affiliations

Authors

Contributions

A.B. and C.D. E. F. wrote the main manuscript text and G.H. I prepared figures 1-3, J.K. L. M prepared tables. All authors reviewed the manuscript.

Corresponding author

Correspondence to Durgesh Singh.

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.

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

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Alaridhee, Z.A.I., Jasim, D.J., Mamadoliyev, I. et al. Synthesis and characterization of Cu-modified ox-g-C3N4 nanosheets as an electrode for green synthesis of phenyl Benzofuran derivatives via C–H functionalization to C–O and C–C bond formation with an electrochemical oxidation system. Res Chem Intermed (2024). https://doi.org/10.1007/s11164-024-05295-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • DOI: https://doi.org/10.1007/s11164-024-05295-5

Keywords

Navigation