Skip to main content
Log in

Cu@MTPOF as an Efficient Catalyst for the C–S Coupling of 2-Mercaptobenzimidazole with Aryl Halides and 2-Halobenzoic Acids

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

The porous organic framework has been receiving significant attention for the past few years because of its various applications, including heterogeneous catalysis. The catalytic activity of the parent porous organic framework is often increased by incorporating or doping metal ions in the framework. In this context, copper has been loaded in a melamine–terephthaldehyde based porous organic framework (MTPOF), and its catalytical activity is successfully examined for the C–S coupling reaction of 2-mercaptobenzimidazole with aryl halides and 2-halobenzoic acids. The MTPOF is synthesized by reacting melamine with terephthaldehyde, and then the copper acetate is integrated in the framework. The MTPOF and Cu@MTPOF have been characterized by FTIR, SEM, EDS, solid-state NMR, BET, TGA-DTG, and XPS analysis. It has been found that Cu@MTPOF is quite effective in catalyzing C–S coupling reaction with Cu@MTPOF, which is effortlessly recuperated and reused multiple times without much change in catalytic activity.

Graphical 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.

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

Similar content being viewed by others

References

  1. Zhang S, Yang Q, Wang C, Luo X, Kim J, Wang Z, Yamauchi Y (2018) Adv Sci 5:1801116

    Article  Google Scholar 

  2. Xu H, Gao J, Jiang D (2015) Nat Chem 7:905–912

    Article  CAS  PubMed  Google Scholar 

  3. Xu S, He J, Jin S, Tan B (2018) J Colloid Interface Sci 509:457–462

    Article  CAS  PubMed  Google Scholar 

  4. Han SS, Furukawa H, Yaghi OM, Goddard WA III (2008) J Am Chem Soc 130:11580–11581

    Article  CAS  PubMed  Google Scholar 

  5. El-Ghazawy RA, Mahmoud AG, Ferreira MJ, Gomes CS, Gomes PT, Shaffei K, Atta AM (2014) J Polym Res 21:1–10

    Google Scholar 

  6. Taskin OS, Ersoy N, Aksu A, Kiskan B, Balkis N, Yagci Y (2016) Polym Int 65:439–445

    Article  CAS  Google Scholar 

  7. Bai L, Phua SZF, Lim WQ, Jana A, Luo Z, Tham HP, Zhao L, Gao Q, Zhao Y (2016) Chem Commun 52:4128–4131

    Article  CAS  Google Scholar 

  8. Fu Q, Wang T, Sun Y, Zheng N, Xie Z, Lu D, Xu Z, Wan X, Zhang Y, Liu Y (2021) Sci China Chem 64:82–91

    Article  CAS  Google Scholar 

  9. Liu J, Wang N, Ma L (2020) Chem Asian J 15:338–351

    Article  CAS  PubMed  Google Scholar 

  10. Lin CY, Zhang D, Zhao Z, Xia Z (2018) Adv Mater 30:1703646

    Article  Google Scholar 

  11. Rohan R, Pareek K, Cai W, Zhang Y, Xu G, Chen Z, Gao Z, Dan Z, Cheng H (2015) J Mater Chem A 3:5132–5139

    Article  CAS  Google Scholar 

  12. Li J, Jing X, Li Q, Li S, Gao X, Feng X, Wang B (2020) Chem Soc Rev 49:3565–3604

    Article  CAS  PubMed  Google Scholar 

  13. Wang Z, Si Z, Cai D, Li GLS, Qin P (2020) J Membr Sci 615:118466

    Article  CAS  Google Scholar 

  14. Liu H, Li X, Ma Z, Sun M, Li M, Zhang Z, Zhang L, Tang Z, Yao Y, Huang B (2021) Nano Lett 21:10284–10291

    Article  CAS  PubMed  Google Scholar 

  15. Chakraborty D, Nandi S, Mullangi D, Haldar S, Vinod CP, Vaidhyanathan R (2019) ACS Appl Mater Interfaces 11:15670–15679

    Article  CAS  PubMed  Google Scholar 

  16. Wang J-C, Kan X, Shang J-Y, Qiao H, Dong Y-B (2020) J Am Chem Soc 142:16915–16920

    Article  CAS  PubMed  Google Scholar 

  17. Zhang W, Jiang P, Wang Y, Zhang J, Gao Y, Zhang P (2014) RSC Adv 4:51544–51547

    Article  CAS  Google Scholar 

  18. Rozhko E, Bavykina A, Osadchii D, Makkee M, Gascon J (2017) J Catal 345:270–280

    Article  CAS  Google Scholar 

  19. Chen G-J, Li X-B, Zhao C-C, Ma H-C, Kan J-L, Xin Y-B, Chen C-X, Dong Y-B (2018) Inorg Chem 57:2678–2685

    Article  CAS  PubMed  Google Scholar 

  20. Yang C, Maenosono S, Duan J, Zhang X (2019) ChemNanoMat 5:957–963

    Article  CAS  Google Scholar 

  21. Chakraborty D, Shekhar P, Singh HD, Kushwaha R, Vinod C, Vaidhyanathan R (2019) Chemistry 14:4767–4773

    CAS  Google Scholar 

  22. Zhang Y, Hu H, Ju J, Yan Q, Arumugam V, Jing X, Cai H, Gao Y (2020) Chin J Catal 41:485–493

    Article  CAS  Google Scholar 

  23. Qian Y, Li D, Han Y, Jiang H-L (2020) J Am Chem Soc 142:20763–20771

    Article  CAS  PubMed  Google Scholar 

  24. Banerjee T, Podjaski F, Kröger J, Biswal BP, Lotsch BV (2021) Nat Rev Mater 6:168–190

    Article  CAS  Google Scholar 

  25. Cheng J-Z, Tan Z-R, Xing Y-Q, Shen Z-Q, Zhang Y-J, Liu L-L, Yang K, Chen L, Liu S-Y (2021) J Mater Chem A 9:5787–5795

    Article  CAS  Google Scholar 

  26. Ghobakhloo F, Azarifar D, Mohammadi M, Keypour H, Zeynali H (2022) Inorg Chem 61(12):4825–4841

    Article  CAS  PubMed  Google Scholar 

  27. Ghorbani-Choghamarani A, Taherinia Z, Mohammadi M (2021) Environ Technol Innov 24:102050

    Article  CAS  Google Scholar 

  28. Ramish SM, Ghorbani-Choghamarani A, Mohammadi M (2022) Sci Rep 12:1–15

    Article  Google Scholar 

  29. Hussain-Khil N, Ghorbani-Choghamarani A, Mohammadi M (2021) Sci Rep 11:1–15

    Article  Google Scholar 

  30. Koolivand M, Nikoorazm M, Ghorbani-Choghamaran A, Mohammadi M (2022) Appl Organomet Chem 48(6):2641–2663

    Google Scholar 

  31. He H, Zhu Q-Q, Yan Y, Zhang H-W, Han Z-Y, Sun H, Chen J, Li C-P, Zhang Z, Du M (2022) Appl Catal B 302:120840

    Article  CAS  Google Scholar 

  32. Zhang Z, Lou Y, Guo C, Jia Q, Song Y, Tian J-Y, Zhang S, Wang M, He L, Du M (2021) Trends Food Sci Technol 118:569–588

    Article  CAS  Google Scholar 

  33. Zhu L, Liang G, Guo C, Xu M, Wang M, Wang C, Zhang Z, Du M (2022) Food Chem 366:130575

    Article  CAS  PubMed  Google Scholar 

  34. Wang Z, Lei Q, Wang Z, Yuan H, Cao L, Qin N, Lu Z, Xiao J, Liu J (2020) Chem Eng J 395:125180

    Article  CAS  Google Scholar 

  35. Yan H, Zhao M, Feng X, Zhao S, Zhou X, Li S, Zha M, Meng F, Chen X, Liu Y (2022) Angew Chem

  36. You J, Liu C, Feng X, Lu B, Xia L, Zhuang X (2022) Carbohydr Polym 288:119332

    Article  CAS  PubMed  Google Scholar 

  37. Wang H, Cui J, Zhao Y, Li Z, Wang J (2021) Green Chem 23:405–411

    Article  CAS  Google Scholar 

  38. Li L, Lu F, Xue R, Ma B, Li Q, Wu N, Liu H, Yao W, Guo H, Yang W (2019) ACS Appl Mater Interfaces 11:26355–26363

    Article  CAS  PubMed  Google Scholar 

  39. Shunmughanathan M, Puthiaraj P, Pitchumani K (2015) ChemCatChem 7:666–673

    Article  CAS  Google Scholar 

  40. Orooji Y, Pakzad K, Nasrollahzadeh M, Tajbakhsh M (2021) Int J Biol Macromol 182:564–573

    Article  CAS  PubMed  Google Scholar 

  41. Yang Y, Niu H, Zhao W, Xu L, Zhang H, Cai Y (2020) RSC Adv 10:29402–29407

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  42. Mullangi D, Nandi S, Shalini S, Sreedhala S, Vinod CP, Vaidhyanathan R (2015) Sci Rep 5:1–12

    Article  Google Scholar 

  43. Gonçalves RS, de Oliveira AB, Sindra HC, Archanjo BS, Mendoza ME, Carneiro LS, Buarque CD, Esteves PM (2016) ChemCatChem 8:743–750

    Article  Google Scholar 

  44. Mohammadian R, Amini MM, Shaabani A (2020) Catal Commun 136:105905

    Article  CAS  Google Scholar 

  45. Heravi MM, Hosseini M, Oskooie HA, Baghernejad B, Farzaneh F (2010) Chin J Chem 28:2045–2048

    Article  CAS  Google Scholar 

  46. Fakhri P, Nasrollahzadeh M, Jaleh B (2014) RSC Adv 4:48691–48697

    Article  CAS  Google Scholar 

  47. Mohazzab BF, Jaleh B, Issaabadi Z, Nasrollahzadeh M, Varma RS (2019) Green Chem 21:3319–3327

    Article  Google Scholar 

  48. Nasrollahzadeh M, Issaabadi Z, Tohidi MM, Mohammad Sajadi S (2018) Chem Rec 18:165–229

    Article  CAS  PubMed  Google Scholar 

  49. Puthiaraj P, Pitchumani K (2014) Chem Eur J 20:8761–8770

    Article  CAS  PubMed  Google Scholar 

  50. Chen M, Zhang J, Liu C, Li H, Yang H, Feng Y, Zhang B (2021) Org Lett 23:1748–1752

    Article  CAS  PubMed  Google Scholar 

  51. Lu G, Huang X, Wu Z, Li Y, Xing L, Gao H, Dong W, Wang G (2019) Appl Surf Sci 493:551–560

    Article  CAS  Google Scholar 

  52. Puthiaraj P, Lee Y-R, Zhang S, Ahn W-S (2016) J Mater Chem A 4:16288–16311

    Article  CAS  Google Scholar 

  53. Nasrollahzadeh M, Sajjadi M, Ghorbannezhad F, Sajadi SM (2018) Chem Rec 18:1409–1473

    Article  CAS  PubMed  Google Scholar 

  54. Zhao X, Yan N (2015) RSC Adv 5:69955–69961

    Article  CAS  Google Scholar 

  55. Shen C, Zhang P, Sun Q, Bai S, Hor TA, Liu X (2015) Chem Soc Rev 44:291–314

    Article  CAS  PubMed  Google Scholar 

  56. Thomas AM, Sherin D, Asha S, Manojkumar T, Anilkumar G (2020) Polyhedron 176:114269

    Article  CAS  Google Scholar 

  57. Molaei S, Tamoradi T, Ghadermazi M, Ghorbani-Choghamarani A (2018) Polyhedron 156:35–47

    Article  CAS  Google Scholar 

  58. Schwab MG, Crespy D, Feng X, Landfester K, Müllen K (2011) Macromol Rapid Commun 32:1798–1803

    Article  CAS  PubMed  Google Scholar 

  59. Schwab MG, Fassbender B, Spiess HW, Thomas A, Feng X, Müllen K (2009) J Am Chem Soc 131:7216–7217

    Article  CAS  PubMed  Google Scholar 

  60. Du J, Zhao Y, Chen J, Zhang P, Gao L, Wang M, Cao C, Wen W, Zhu C (2017) RSC Adv 7:33929–33936

    Article  CAS  Google Scholar 

  61. Singh G, Kumar M, Bhalla V (2018) Green Chem 20:5346–5357

    Article  CAS  Google Scholar 

  62. Horton DA, Bourne GT, Smythe ML (2003) Chem Rev 103:893–930

    Article  CAS  PubMed  Google Scholar 

  63. Ge X, Chen X, Qian C, Zhou S (2016) RSC Adv 6:58898–58906

    Article  CAS  Google Scholar 

  64. Gammon W, Kraft O, Reilly A, Holloway B (2003) Carbon 41:1917–1923

    Article  CAS  Google Scholar 

  65. Yang G, Han H, Du C, Luo Z, Wang Y (2010) Polymer 51:6193–6202

    Article  CAS  Google Scholar 

  66. Sadhasivam V, Sankar B, Elamathi G, Mariyappan M, Siva A (2020) Rev Chem Intermed 46:681–700

    Article  CAS  Google Scholar 

  67. Sengupta D, Basu B (2014) Org Med Chem Lett 4:1–10

    Article  Google Scholar 

  68. Sekar R, Srinivasan M, Marcelis AT, Sambandam A (2011) Tetrahedron Lett 52:3347–3352

    Article  CAS  Google Scholar 

  69. Pulakhandam SK, Katari NK, Manda RPR (2017) J Chem Sci 129:203–210

    Article  CAS  Google Scholar 

  70. Ge X, Song W, Chen X, Qian C, Zhou S, Liu X (2021) Colloids Surf A 616:126263

    Article  CAS  Google Scholar 

  71. Huang L, Yang J, Xu L, Wu X, Yu L, Bao W, Chen D (2015) Heteroat Chem 26:361–366

    Article  CAS  Google Scholar 

  72. Guozhen H, Yuan HT, Jie Z, Dan Z, Shuangli Z, Shiqing H (2013) Tetrahedron Lett 54:5318–5321

    Article  Google Scholar 

Download references

Acknowledgements

The authors would like to thank the Director, VNIT, Nagpur, India, for the financial assistance and facilities provided. The authors also thankful to DST, India for providing an instrumental facility under FIST programme and we are also grateful to STIC Cochin for material characterization facility.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Umesh R. Pratap.

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 1028 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Dani, S.H., Pratap, U.R. Cu@MTPOF as an Efficient Catalyst for the C–S Coupling of 2-Mercaptobenzimidazole with Aryl Halides and 2-Halobenzoic Acids. Catal Lett 153, 1708–1718 (2023). https://doi.org/10.1007/s10562-022-04092-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-022-04092-2

Keywords

Navigation