SpringerLink
Log in

Co3O4 nanoparticles embedded in triple-shelled graphitic carbon nitride (Co3O4/TSCN): a new sustainable and high-performance hierarchical catalyst for the Pd/Cu-free Sonogashira–Hagihara cross-coupling reaction in solvent-free conditions

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

Abstract

Inspired by the synthesis of triple-shelled periodic mesoporous organosilica hollow spheres, a straightforward and controllable approach for the preparation of Co3O4 NPs embedded in triple-shelled graphitic carbon nitride has been established through a combinatorial route comprising the hard-templating technique and impregnation method. A series of various techniques such as FT-IR, XRD, BET, TEM, FE-SEM, EDX, EDX map**, TGA, and ICP-OES have been used for the full characterization of the catalyst. It was found that the Co3O4/TSCN has a high performance to promote Sonogashira–Hagihara cross-coupling reaction in solvent-free conditions. Interestingly, the architecture of the catalyst provides not only the high dispersion loading of the Co3O4 NPs on the support, but also facilitates the favorable mass transfer through the catalyst structure. The catalyst could be readily separated from the reaction mixture by filtration method and used again up to five times without any evident decrease in catalytic activity.

Graphical abstract

The superior catalytic performance of the Co3O4/TSCN as a new sustainable hierarchical catalyst has been presented for Pd/Cu-free Sonogashira–Hagihara cross-coupling reaction under solvent-free conditions

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

Access this article

Log in via an institution

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Institutional subscriptions

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

Similar content being viewed by others

References

  1. H.C. Shen, Selected Applications of Transition Metal-Catalyzed Carbon-Carbon Cross-Coupling Reactions in the Pharmaceutical Industry, in Applications of Transition Metal Catalysis in Drug Discovery and Development. ed. by M.L. Crawley, B.M. Trost (John Wiley & Sons Inc, Hoboken, 2012), pp. 25–95

    Chapter  Google Scholar 

  2. J.A. Marsden, M.M. Haley, Cross-coupling reactions to sp carbon atoms, in Metal-Catalyzed Cross-Coupling Reactions. 2nd edn, ed. by A.D. de Meijere (Wiley-VCH, Weinheim, 2004), pp. 317–394

    Chapter  Google Scholar 

  3. C.C.C.J. Seechurn, M.O. Kitching, T.J. Colacot, V. Snieckus, Angew. Chem. Int. Ed. 51, 5062 (2012)

    Article  CAS  Google Scholar 

  4. J. Boström, D.G. Brown, R.J. Young, G.M. Keserü, Nat. Rev. Drug Discovery 17, 709 (2018)

    Article  PubMed  CAS  Google Scholar 

  5. D.G. Brown, J. Boström, J. Med. Chem. 59, 4443 (2016)

    Article  CAS  PubMed  Google Scholar 

  6. R.W. Dugger, J.A.D. Ragan, H.B. Ripin, Org. Process Res. Dev. 9, 253 (2005)

    Article  CAS  Google Scholar 

  7. Á. Molnár, Chem. Rev. 111, 2251 (2011)

    Article  PubMed  CAS  Google Scholar 

  8. L.X. Yin, J. Liebscher, Chem. Rev. 107, 133 (2007)

    Article  CAS  PubMed  Google Scholar 

  9. S. Sisodiya, L.R. Wallenberg, E. Lewin, O.F. Wendt, Appl. Catal. A 503, 69 (2015)

    Article  CAS  Google Scholar 

  10. Q. Chen, F. Gao, H. Tang, M. Yao, Q. Zhao, Y. Shi, Y. Dang, Ch. Cao, ACS Catal. 9, 3730 (2019)

    Article  CAS  Google Scholar 

  11. A. Elhage, A.E. Lanterna, J.C. Scaiano, ACS Sustain. Chem. Eng. 6, 1717 (2018)

    Article  CAS  Google Scholar 

  12. B. Wang, Y. Wang, J. Li, X. Guo, G. Bai, X. Tong, G. **, X. Guo, Catal. Sci. Technol. 8, 3357 (2018)

    Article  CAS  Google Scholar 

  13. A.A. Liori, I.K. Stamatopoulos, Eur. J. Chem. 2018, 6134 (2018)

    CAS  Google Scholar 

  14. G.M. Roberts, W. Lu, L.K. Woo, RSC Adv. 5, 18960 (2015)

    Article  CAS  Google Scholar 

  15. A. Dewan, M. Sarmah, U. Bora, A.J. Thakur, Tetrahedron Lett. 57, 3760 (2016)

    Article  CAS  Google Scholar 

  16. B. **, F. Gallou, J. Reilly, B.H. Lipshutz, Chem. Sci. 10, 3481 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  17. K.C. Dissanayake, P.O. Ebukuyo, Y.J. Dhahir, K. Wheeler, H. He, Chem. Commun. 55, 4973 (2019)

    Article  CAS  Google Scholar 

  18. D.A. Alonso, A. Baeza, R. Chinchilla, C. Gómez, G. Guillena, I.M. Pastor, D.J. Ramón, Catalysts 8, 202 (2018)

    Article  CAS  Google Scholar 

  19. J. Kou, A. Saha, Ch. Bennett-Stamper, R.S. Varma, Chem. Commun. 48, 5862 (2012)

    Article  CAS  Google Scholar 

  20. A.R. Hajipour, F. Rezaei, Z. Khorsandi, Green Chem. 19, 1353 (2017)

    Article  CAS  Google Scholar 

  21. O. Vechorkin, D. Barmaz, V. Proust, X. Hu, J. Am. Chem. Soc. 131, 12078 (2009)

    Article  CAS  PubMed  Google Scholar 

  22. V.K. Kanuru, G. Kyriakou, S.K. Beaumont, A.C. Papageorgiou, D.J. Watson, R.M. Lambert, J. Am. Chem. Soc. 132, 8081 (2010)

    Article  CAS  PubMed  Google Scholar 

  23. M. Bakherad, A. Keivanloo, S. Mihanparast, Synth. Commun. 40, 179 (2009)

    Article  CAS  Google Scholar 

  24. G. Evano, N. Blanchard, M. Toumi, Chem. Rev. 108, 3054 (2008)

    Article  CAS  PubMed  Google Scholar 

  25. H. Plenio, Angew. Chem. Int. Ed. 47, 6954 (2008)

    Article  CAS  Google Scholar 

  26. M.B. Thathagar, J. Beckers, G. Green Chem. 6, 215 (2004)

    Article  CAS  Google Scholar 

  27. K. Okuro, M. Furuune, M. Enna, M. Miura, M. Nomura, J. Org. Chem. 58, 4716 (1993)

    Article  CAS  Google Scholar 

  28. J.-H. Li, D.-P. Wang, S.-F. Pi, Y.-X. **e, M.-B. Zhang, C. Hu, J. Org. Chem. 72, 2053 (2007)

    Article  CAS  PubMed  Google Scholar 

  29. F. Monnier, F.O. Turtaut, L. Duroure, M. Taillefer, Org. Lett. 10, 3203 (2008)

    Article  CAS  PubMed  Google Scholar 

  30. G. Bates, D. Venkataraman, Synthesis 10, 1706 (2005)

    Google Scholar 

  31. M. Carril, A. Correa, C. Bolm, Angew. Chem. Int. Ed. 47, 4862 (2008)

    Article  CAS  Google Scholar 

  32. E. Zuidema, C. Bolm, Chem. Eur. J. 16, 4181 (2010)

    Article  CAS  PubMed  Google Scholar 

  33. C. Sanchez, B. Julián, P. Belleville, M. Popall, J. Mater. Chem. 15, 3559 (2005)

    Article  CAS  Google Scholar 

  34. E.-Y. Jeong, S.-E. Park, Res. Chem. Intermed. 38, 1237 (2012)

    Article  CAS  Google Scholar 

  35. A. Yaghoubi, M.G. Dekamin, ChemistrySelect 2, 9236 (2017)

    Article  CAS  Google Scholar 

  36. A. Yaghoubi, M.G. Dekamin, E. Arefi, B. Karimi, J. Colloid Interface Sci. 505, 956 (2017)

    Article  CAS  PubMed  Google Scholar 

  37. S.S. Park, S. Moorthy, C.-S. Ha, NPG Asia Mater. 6, e96 (2014)

    Article  CAS  Google Scholar 

  38. Z.G. Teng, X.D. Su, Y.Y. Zheng, J.J. Zhang, Y. Liu, S.J. Wang, J. Wu, G.T. Chen, J.D. Wang, D.Y. Zhao, J. Am. Chem. Soc. 137, 7935 (2015)

    Article  CAS  PubMed  Google Scholar 

  39. J. Zhu, P. **ao, H. Li, S.A.C. Carabineiro, ACS Appl. Mater. Interfaces 6, 16449 (2014)

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  41. Q. Han, B. Wang, Y. Zhao, C.G. Hu, L.T. Qu, Angew. Chem. Int. Ed. 54, 11433 (2015)

    Article  CAS  Google Scholar 

  42. Y. Zheng, J. Liu, J. Liang, M. Jaronietc, S.Z. Qiao, Energy Environ. Sci. 5, 6717 (2015)

    Article  CAS  Google Scholar 

  43. Y. Wang, X.C. Wang, M. Antonietti, Angew. Chem. Int. Ed. 51, 68 (2012)

    Article  CAS  Google Scholar 

  44. Q.F. Deng, L. Liu, X.Z. Lin, G.H. Du, Y.P. Liu, Z.Y. Yuan, Chem. Eng. J. 203, 63 (2012)

    Article  CAS  Google Scholar 

  45. D. Yang, T. Jiang, T. Wu, P. Zhang, H. Han, B. Han, Catal. Sci. Technol. 6, 193 (2016)

    Article  Google Scholar 

  46. C. Guo, M. Chu, Q. Liu, Y. Liu, D. Guo, X. Liu, Appl. Catal. A. 246, 303 (2003)

    Article  CAS  Google Scholar 

  47. Zh. Tong, D. Yang, Zh. Li, Y. Nan, F. Ding, Y. Shen, Zh. Jiang, ACS Nano 11, 1103 (2017)

    Article  CAS  PubMed  Google Scholar 

  48. S.S.E. Ghodsinia, B. Akhlaghinia, Green Chem. 21, 3029 (2019)

    Article  CAS  Google Scholar 

  49. A. Mohammadinezhad, B. Akhlaghinia, New J. Chem. 43, 15525 (2019)

    Article  CAS  Google Scholar 

  50. A. Mohammadinezhad, B. Akhlaghinia, Green Chem. 23, 5625 (2017)

    Article  Google Scholar 

  51. Z. Zarei, B. Akhlaghinia, RSC Adv. 6, 106473 (2016)

    Article  CAS  Google Scholar 

  52. M. Ghasemzadeh, B. Akhlaghinia, New J. Chem. 43, 5341 (2019)

    Article  CAS  Google Scholar 

  53. M. Ghasemzadeh, B. Akhlaghinia, ChemistrySelect 3, 3161 (2018)

    Article  CAS  Google Scholar 

  54. N. Razavi, B. Akhlaghinia, R. Jahanshahi, Catal. Lett. 147, 360 (2017)

    Article  CAS  Google Scholar 

  55. R. Jahanshahi, B. Akhlaghinia, Catal. Lett. 147, 2640 (2017)

    Article  CAS  Google Scholar 

  56. M. Zarghania, B. Akhlaghinia, RSC Adv. 6, 38592 (2016)

    Article  Google Scholar 

  57. F. Azimov, I. Markova, V. Stefanova, Kh. Sharipov, J. Univ. Chem. Technol. Metall. 47, 333 (2012)

    CAS  Google Scholar 

  58. F. Berube, S. Kaliaguine, Microporous Mesoporous Mater. 115, 469 (2008)

    Article  CAS  Google Scholar 

  59. R.C.S. Azevedo, R.G. Sousa, W.A.A. Macedo, E.M.B. Sousa, J. Solgel Sci. Technol. 72, 208 (2014)

    Article  CAS  Google Scholar 

  60. H. Chaudhuri, S. Dash, S. Ghorai, S. Pal, A. Sarkar, Environ. Chem. Eng. 4, 157 (2016)

    Article  CAS  Google Scholar 

  61. P. Qiu, H. Chen, F. Jiang, RSC Adv. 4, 39969 (2014)

    Article  CAS  Google Scholar 

  62. H.-L. Zhu, Y.-Q. Zheng, Electrochim. Acta. 8, 372 (2017)

    Google Scholar 

  63. L. Estepa, M. Daudon, Biospectroscopy 3, 347 (1997)

    Article  CAS  Google Scholar 

  64. S.H. Wu, D.H. Chen, Interface Sci. 259, 282 (2003)

    Article  CAS  Google Scholar 

  65. Q. Yao, Z.H. Lu, K. Yang, X. Chen, M. Zhu, Sci. Rep. 5, 15186 (2015)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  66. S.J. Choi, W.H. Ryu, S.J. Kim, H.J. Cho, I.D. Kim, J. Mater. Chem. B 2, 7160 (2014)

    Article  CAS  PubMed  Google Scholar 

  67. J. Li, S.B. Tang, L. Lu, H.C. Zeng, J. Am. Chem. Soc. 129, 9401 (2007)

    Article  CAS  PubMed  Google Scholar 

  68. S.G. Chatterjee, S. Chatterjee, A.K. Ray, A.K. Chakraborty, Sens. Actuators B 221, 1170 (2015)

    Article  CAS  Google Scholar 

  69. Y.Y. Liang, Y.G. Li, H.L. Wang, J.G. Zhou, J. Wang, T. Regier, H. Dai, J. Nat. Mater. 10, 780 (2011)

    Article  CAS  Google Scholar 

  70. H.J. Kim, J.H. Lee, Sens. Actuator B-Chem. 192, 607 (2014)

    Article  CAS  Google Scholar 

  71. C. Wang, J.W. Zhu, S.M. Liang, H.P. Bi, Q.F. Han, X.H. Liu, X. Wang, J. Mater. Chem. A 2, 18635 (2014)

    Article  CAS  Google Scholar 

  72. J. Liua, Y. Songb, H. Xua, X. Zhu, J. Lian, Y. Xua, Y. Zhao, L. Huang, H. Ji, H. Li, J. Colloid Interface Sci. 494, 38 (2017)

    Article  CAS  Google Scholar 

  73. R.M. Rojas, E. Vila, O. García, J.L.M. de Vidales, J. Mater. Chem. 4, 1635 (1994)

    Article  CAS  Google Scholar 

  74. R. Garavaglia, C.M. Mari, S. Trasatti, C. de Asmundis, Surf. Technol. 19, 197 (1983)

    Article  CAS  Google Scholar 

  75. T. Kavitha, S. Haider, T. Kamal, J. Alloys Compd. 704, 296 (2017)

    Article  CAS  Google Scholar 

  76. P. Suyana, P. Ganguly, B.N. Nair, A.P. Mohamed, K.G.K. Warrier, U.S. Hareesh, Environ. Sci NANO 4, 212 (2017)

    Article  CAS  Google Scholar 

  77. H. Shao, X. Zhao, Y. Wang, R. Mao, Y. Wang, M. Qiao, S. Zhao, Y. Zhu, Appl. Catal. 218, 810 (2017)

    Article  CAS  Google Scholar 

  78. J. Xu, K.-Z. Long, T. Chen, B. Xue, Y.-X. Li, Y. Cao, Catal. Sci. Technol. 3, 3192 (2013)

    Article  CAS  Google Scholar 

  79. G.W.V. Cave, C.L. Raston, J.L. Scott, Chem. Commun. 2011, 2159 (2001)

    Article  CAS  Google Scholar 

  80. A.F. Littke, G.C. Fu, Angew. Chem. Int. Ed. 41, 4176 (2002)

    Article  CAS  Google Scholar 

  81. F. Durap, M. Rakap, M. Aydemir, S. Özkar, Appl. Catal. A 382, 339 (2010)

    Article  CAS  Google Scholar 

  82. M. Kataria, S. Pramanik, N. Kaur, M. Kumar, V. Bhalla, Green Chem. 18, 1495 (2016)

    Article  CAS  Google Scholar 

  83. M. Ghasemzadeh, B. Akhlaghinia, ChemistrySelect 4, 1542 (2019)

    Article  CAS  Google Scholar 

  84. M. Rajabzadeh, R. Khalifeh, H. Eshghi, M. Bakavoli, J. Catal. 360, 261 (2018)

    Article  CAS  Google Scholar 

  85. A. Mohammadinezhad, B. Akhlaghinia, ChemistrySelect 4, 12455 (2019)

    Article  CAS  Google Scholar 

  86. X. Kong, Sh. Li, M. Strømme, Xu. Ch, Nanomaterials 9, 1020 (2019)

    Article  CAS  PubMed Central  Google Scholar 

  87. D. Chisholm, R. Lamb, T. Pallett, A. Whiting, Chem. Sci. 10, 4673 (2019)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  88. R. Chinchilla, C. ́ Najera, Chem. Rev. 107, 874 (2007).

  89. H. Veisi, A. Sedrpoushan, B. Maleki, M. Hekmati, M. Heidari, S. Hemmati, Appl. Organometal. Chem. 29, 834 (2015)

    Article  CAS  Google Scholar 

  90. M. Gholinejad, J. ChemPlusChem 80, 973 (2015)

    Article  CAS  Google Scholar 

  91. E. Fernández, M.A.R. Crespo, I. Domínguez, P.R. Marqués, J.O. Meseguer, L. Liu, M.C. Antonino, R. Gavara, J.C.H. Garrido, M. Boronat, A.L. Corma, J. Am. Chem. Soc. 141, 1928 (2019)

    Article  PubMed  CAS  Google Scholar 

  92. S. Elavarasan, B. Baskar, C. Senthil, A. Bhanja, P. Selvam, RSC Adv. 6, 49376 (2016)

    Article  CAS  Google Scholar 

  93. F.D. Firuzabadi, Z. Asadi, F. Panahi, RSC Adv. 6, 101061 (2016)

    Article  CAS  Google Scholar 

  94. S. Roy, K.K. Senapati, P. Phukan, Res. Chem. Intermed. 41, 5753 (2015)

    Article  CAS  Google Scholar 

  95. M. Shaker, S. Adam, J. Organomet. Chem. 903, e120985 (2019)

    Article  CAS  Google Scholar 

  96. A.R. Hajipour, S. Jajarmi, Appl. Organomet. Chem. 32, e399 (2018)

    Article  CAS  Google Scholar 

  97. Y. Liu, V. Blanchard, G. Danoun, Z. Zhang, A. Tlili, W. Zhang, F. Monnier, A. Van Der Lee, J. Mao, M. Taillefer, ChemistrySelect 2, 11599 (2017)

    Article  CAS  Google Scholar 

  98. A.A. Liori, I.K. Stamatopoulos, A.T. Papastavrou, A. Pinaka, G.C. Vougioukalakis, Eur. J. Org. Chem. 2018, 6134 (2018)

    Article  CAS  Google Scholar 

  99. Ch. H. Lin, Y. J. Wang, Ch. F. Lee, Eur. J. Org. Chem. 2010, 4368 (2010).

    Google Scholar 

  100. J.Y. Song, X. Zhou, H. Song, Y. Liu, H.Y. Zhao, Z.Z. Sun, W.Y. Chu, ChemCatChem 10, 758 (2018)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge the partial support of this study by Ferdowsi University of Mashhad Research Council (Grant no. p/3/39491).

Author information

Authors and Affiliations

  1. Department of Chemistry, Faculty of Science, Ferdowsi University of Mashhad, 9177948974, Mashhad, Iran

    Sara S. E. Ghodsinia, Batool Akhlaghinia & Roya Jahanshahi

Authors
  1. Sara S. E. Ghodsinia
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Batool Akhlaghinia
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Roya Jahanshahi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Batool Akhlaghinia.

Ethics declarations

Conflict of interest

There is no conflict of interest for each contributing author.

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 2271 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ghodsinia, S.S.E., Akhlaghinia, B. & Jahanshahi, R. Co3O4 nanoparticles embedded in triple-shelled graphitic carbon nitride (Co3O4/TSCN): a new sustainable and high-performance hierarchical catalyst for the Pd/Cu-free Sonogashira–Hagihara cross-coupling reaction in solvent-free conditions. Res Chem Intermed 47, 3217–3244 (2021). https://doi.org/10.1007/s11164-021-04466-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-021-04466-y

Keywords

Search

Navigation