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Synthesis, characterization, and application of zinc supported on ionic liquid‐based periodic mesoporous organosilica (Zn@PMO-IL) in A3-coupling reaction for the synthesis of propargylamines

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Abstract

The present paper shows the preparation of a highly porous periodic mesoporous organosilica (PMO) including the ionic liquid pore walls that supported with zinc ions onto PMO-IL (Zn@PMO-IL). Moreover, the material was characterized using field emission‐scanning electron microscopy, transmission electron microscopy, inductively coupled plasma, and N2 adsorption–desorption. Likewise, the catalytic activity of the Zn@PMO-IL, illustrating a highly efficient nanocatalyst for the synthesis of propargylamines through three-component A3-coupling reaction of various aldehydes, amines, and arylacetylene. The results demonstrate an eco-friendly and appealing method with high efficiency and facile work-up procedure. Furthermore, the nanocatalyst can be revived by a simple filtration process and reuse at least five successive runs without considerable reducing in its activity.

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References

  1. Singh MS, Chowdhury S (2012) RSC Adv 2:4547

    Article  CAS  Google Scholar 

  2. Das D (2016) Chem Select 1:1959

    CAS  Google Scholar 

  3. Cioc RC, Ruijter E, Orru RV (2014) Green Chem 16:2958

    Article  CAS  Google Scholar 

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

    Article  CAS  PubMed  Google Scholar 

  5. Karimi B, Mansouri F, Mirzaei HM (2015) ChemCatChem 7:1736

    Article  CAS  Google Scholar 

  6. Sakaguchi S, Kubo T, Ishii Y (2001) Angew Chem Int Ed 40:2534

    Article  CAS  Google Scholar 

  7. Albaladejo MJ, Alonso F, Moglie Y, Yus M (2012) Eur J Org Chem 2012:3093

    Article  CAS  Google Scholar 

  8. Dang GH, Dang TT, Le DT, Truong T, Phan NT (2014) J Catal 319:258

    Article  CAS  Google Scholar 

  9. Bobadilla LF, Blasco T, Odriozola JA (2013) Phys Chem Chem Phys 15:16927

    Article  CAS  PubMed  Google Scholar 

  10. Soengas R, Navarro Y, Iglesias MJ, López-Ortiz F (2018) Molecules 23:2975

    Article  PubMed Central  CAS  Google Scholar 

  11. Peshkov VA, Pereshivko OP, Van der Eycken EV (2012) Chem Soc Rev 41:3790

    Article  CAS  PubMed  Google Scholar 

  12. Mo JN, Su J, Zhao J (2019) Molecules 24:1216

    Article  PubMed Central  CAS  Google Scholar 

  13. Kochman A, Skolimowski J, Gêbicka L, Metodiewa D (2003) Pol J Pharmacol 55:389

    CAS  PubMed  Google Scholar 

  14. Fleming JJ, Du Bois J (2006) J Am Chem Soc 128:3926

    Article  CAS  PubMed  Google Scholar 

  15. Sayyahi S, Saghanezhad SJ (2019) Mini-Rev Org Chem 16:361

    Article  CAS  Google Scholar 

  16. Lauder K, Toscani A, Scalacci N, Castagnolo D (2017) Chem Rev 117:14091

    Article  CAS  PubMed  Google Scholar 

  17. Saha TK, Das R (2018) ChemistrySelect 3:147

    Article  CAS  Google Scholar 

  18. Nakamura S, Ohara M, Nakamura Y, Shibata N, Toru T (2010) Chem Eur J 16:2360

    Article  CAS  PubMed  Google Scholar 

  19. Wei C, Li CJ (2002) J Am Chem Soc 124:5638

    Article  CAS  PubMed  Google Scholar 

  20. Rokade BV, Barker J, Guiry PJ (2019) Chem Soc Rev 48:4766

    Article  CAS  PubMed  Google Scholar 

  21. Jesin I, Nandi GC (2019) Eur J Org Chem 2019:2704

    Article  CAS  Google Scholar 

  22. Li P, Zhang Y, Wang L (2009) Chem Eur J 15:2045

    Article  CAS  PubMed  Google Scholar 

  23. Ryaná Bonfield E (2007) Org Biomol Chem 5:435

    Article  Google Scholar 

  24. Namitharan K, Pitchumani K (2010) Eur J Org Chem 2010:411

    Article  CAS  Google Scholar 

  25. Sakaguchi S, Mizuta T, Furuwan M, Kubo T, Ishii Y (2004) Chem Commun 2004:1638

    Article  CAS  Google Scholar 

  26. Li Z, Wei C, Chen L, Varma RS, Li CJ (2004) Tetrahedron Lett 45:2443

    Article  CAS  Google Scholar 

  27. Wei C, Li CJ (2003) J Am Chem Soc 125:9584

    Article  CAS  PubMed  Google Scholar 

  28. Pal N, Bhaumik A (2015) RSC Adv 5:24363

    Article  CAS  Google Scholar 

  29. Zhang Y, Riduan SN (2012) Chem Soc Rev 41:2083

    Article  CAS  PubMed  Google Scholar 

  30. Kuang Y, Islam NM, Nabae Y, Hayakawa T, Kakimoto MA (2010) Angew Chem Int Ed 49:436

    Article  CAS  Google Scholar 

  31. Aghajani M, Safaei E, Karimi B (2017) Synth Met 233:63

    Article  CAS  Google Scholar 

  32. Abdollahi-Alibeik M, Moaddeli A (2014) RSC Adv 4:39759

    Article  CAS  Google Scholar 

  33. Kumar Dutta D, Jyoti Borah B, Pollov Sarmah P (2015) Catal Rev 57:257

    Article  CAS  Google Scholar 

  34. Aghajani M, Monadi N (2018) Appl Organomet Chem 32:e4433

    Article  CAS  Google Scholar 

  35. Park SS, Moorthy MS, Ha CS (2014) Korean J Chem Eng 31:1707

    Article  CAS  Google Scholar 

  36. Ha CS, Park SS (2019) PMOs for catalytic applications. In: Periodic mesoporous organosilicas. Springer, Singapore

  37. Van Der Voort P, Esquivel D, De Canck E, Goethals F, Van Driessche I, Romero-Salguero FJ (2013) Chem Soc Rev 42:3913

    Article  PubMed  Google Scholar 

  38. Karimi B, Tavakolian M, Akbari M, Mansouri F (2018) ChemCatChem 10:3173

    Article  CAS  Google Scholar 

  39. Giacalone F, Gruttadauria M (2016) ChemCatChem 8:664

    Article  CAS  Google Scholar 

  40. Karimi B, Naderi Z, Khorasani M, Mirzaei HM, Vali H (2016) ChemCatChem 8:906

    Article  CAS  Google Scholar 

  41. Rostamnia S, Doustkhah E, Bulgar R, Zeynizadeh B (2016) Microporous Mesoporous Mater 225:272

    Article  CAS  Google Scholar 

  42. Karimi B, Khorasani M, Bakhshandeh Rostami F, Elhamifar D, Vali H (2015) ChemPlusChem 80:990

    Article  CAS  PubMed  Google Scholar 

  43. Nasr-Esfahani M, Elhamifar D, Amadeh T, Karimi B (2015) RSC Adv 5:13087

    Article  CAS  Google Scholar 

  44. Elhamifar D, Kazempoor S (2016) J Mol Catal Chem 415:74

    Article  CAS  Google Scholar 

  45. Karimi B, Gholinejad M, Khorasani M (2012) Chem Commun 48:8961

    Article  CAS  Google Scholar 

  46. Gholinejad M, Karimi B, Aminianfar A, Khorasani M (2015) ChemPlusChem 80:1573

    Article  CAS  PubMed  Google Scholar 

  47. Baharfar R, Zareyee D, Allahgholipour SL (2019) Appl Organomet Chem 33:e4805

    Article  CAS  Google Scholar 

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Acknowledgements

The authors acknowledge the Research Council of Mazandaran University for financial support of this research project.

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Correspondence to Robabeh Baharfar.

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Allahgholipour, S.L., Baharfar, R. Synthesis, characterization, and application of zinc supported on ionic liquid‐based periodic mesoporous organosilica (Zn@PMO-IL) in A3-coupling reaction for the synthesis of propargylamines. Monatsh Chem 151, 991–997 (2020). https://doi.org/10.1007/s00706-020-02628-z

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