Skip to main content

Advertisement

SpringerLink
Log in

Efficient synthesis of symmetrical anhydrides by cross dehydrogenative coupling of aryl aldehydes over CuFe2O4 nanoparticles

  • Original Paper
  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Abstract

Nano copper ferrite catalyst is prepared and characterized by scanning electron microscopy, energy dispersive X-ray, X-ray diffraction, vibrational sample magnetometry, and Fourier transform infrared. The catalytic activity is probed for cross-dehydrogenative coupling of aromatic aldehydes in the presence of tert-butyl hydroperoxide as the oxidant. This catalytic protocol appears as a simple, rather cheap, clean, and efficient practical strategy for the synthesis of symmetrical anhydrides, with proper efficiency (66%). The catalyst can be easily separated from the reaction mixture by an external magnet and reused several times in subsequent reactions, without any measurable loss of its efficiency.

Graphic abstract

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

Access this article

Log in via an institution

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

Instant access to the full article PDF.

Institutional subscriptions

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

Similar content being viewed by others

References

  1. Muralidharan S, Saraswathy V, Berchmans LJ, Thangavel K, Ann KY (2010) Sens Actuators B 145:225

    Article  CAS  Google Scholar 

  2. Yan S, Dong L, Chen Z, Wang X, Feng Z (2014) J Magn Magn Mater 353:47

    Article  CAS  Google Scholar 

  3. Polshettiwar V, Varma RS (2010) Tetrahedron 66:1091

    Article  CAS  Google Scholar 

  4. Patzke GR, Zhou Y, Kontic R, Conrad F (2011) Angew Chem Int Ed 50:826

    Article  CAS  Google Scholar 

  5. Eidi E, Kassaee MZ, Nasresfahani Z (2016) Appl Organomet Chem 30:561

    Article  CAS  Google Scholar 

  6. Eidi E, Kassaee MZ, Cummings PT (2018) Res Chem Intermed 44:5787

    Article  CAS  Google Scholar 

  7. Moghaddam FM, Tavakoli G, Rezvani HR (2015) Catal Commun 60:82

    Article  CAS  Google Scholar 

  8. Monnier F, Taillefer M (2009) Angew Chem Int Ed 48:6954

    Article  CAS  Google Scholar 

  9. Liu C, Zhang H, Shi W, Lei A (2011) Chem Rev 111:1780

    Article  CAS  PubMed  Google Scholar 

  10. Stefani HA, Guarezemini AS, Cella R (2010) Tetrahedron 66:7871

    Article  CAS  Google Scholar 

  11. Li C-J (2008) Acc Chem Res 42:335

    Article  Google Scholar 

  12. Singh S, Yadav BC, Gupta VD, Dwivedi PK (2012) Mater Res Bull 47:3538

    Article  CAS  Google Scholar 

  13. Haija MA, Ayesh AI, Ahmed S, Katsiotis MS (2016) Appl Surf Sci 369:443

    Article  CAS  Google Scholar 

  14. Haija MA, Abu-Hani AFS, Hamdan N, Stephen S, Ayesh AI (2017) J Alloys Compd 690:461

    Article  Google Scholar 

  15. Maaz K, Karim S, Mumtaz A, Hasanain SK, Liu J, Duan JL (2009) J Magn Magn Mater 321:1838

    Article  CAS  Google Scholar 

  16. Manova E, Kunev B, Paneva D, Mitov I, Petrov L, Estournès C, D’Orléan C, Rehspringer J, Kurmoo M (2004) Chem Mater 16:5689

    Article  CAS  Google Scholar 

  17. Liu C, Zou B, Rondinone AJ, Zhang ZJ (2000) J Phys Chem B 104:1141

    Article  CAS  Google Scholar 

  18. Chen D, Chen D, Jiao X, Zhao Y, He M (2003) Powder Technol 133:247

    Article  CAS  Google Scholar 

  19. Rajput JK, Arora P, Kaur G, Kaur M (2015) Ultrason Sonochem 26:229

    Article  CAS  PubMed  Google Scholar 

  20. Kumar AS, Thulasiram B, Laxmi SB, Rawat VS, Sreedhar B (2014) Tetrahedron 70:6059

    Article  Google Scholar 

  21. Dandia A, Jain AK, Sharma S (2013) RSC Adv 3:2924

    Article  CAS  Google Scholar 

  22. Miyashita M, Shiina I, Miyoshi S, Mukaiyama T (1993) Bull Chem Soc Jpn 66:1516

    Article  CAS  Google Scholar 

  23. Shiina I, Nakata K, Ono K, Onda YS, Itagaki M (2010) J Am Chem Soc 132:11629

    Article  CAS  PubMed  Google Scholar 

  24. Mukaiyama T, Shiina I, Miyashita M (1992) Chem Lett 21:625

    Article  Google Scholar 

  25. Mukaiyama T, Izumi J, Miyashita M, Shiina I (1993) Chem Lett 22:907

    Article  Google Scholar 

  26. Kazemi F, Kiasat AR, Mombaini B (2007) Synth Commun 37:3219

    Article  CAS  Google Scholar 

  27. Kocz R, Roestamadji J, Mobashery S (1994) J Org Chem 59:2913

    Article  CAS  Google Scholar 

  28. Keshavamurthy KS, Vankar YD, Dhar DN (1982) Synthesis 1982:506

    Article  Google Scholar 

  29. Stadler A, Kappe CO (2001) Tetrahedron 57:3915

    Article  CAS  Google Scholar 

  30. Mestres R, Palomo C (1981) Synthesis 1981:218

    Article  Google Scholar 

  31. Kaminski ZJ, Kolesinska B, Małgorzata M (2004) Synth Commun 34:3349

    Article  CAS  Google Scholar 

  32. Zhang C, Zong X, Zhang L, Jiao N (2012) Org Lett 14:3280

    Article  CAS  PubMed  Google Scholar 

  33. Wang T, Chen S, Shao A, Gao M, Huang Y, Lei A (2014) Org Lett 17:118

    Article  CAS  PubMed  Google Scholar 

  34. Allen CL, Williams JMJ (2011) Chem Soc Rev 40:3405

    Article  CAS  PubMed  Google Scholar 

  35. Biju AT, Kuhl N, Glorius F (2011) Acc Chem Res 44:1182

    Article  CAS  PubMed  Google Scholar 

  36. Liu X, Jensen KF (2012) Green Chem 14:1471

    Article  CAS  Google Scholar 

  37. Ke Q, Zhang B, Hu B, Jin Y, Lu G (2015) Chem Commun 51:1012

    Article  CAS  Google Scholar 

  38. Zeng J-W, Liu Y-C, Hsieh P-A, Huang Y-T, Yi C-L, Badsara SS, Lee C-F (2014) Green Chem 16:2644

    Article  CAS  Google Scholar 

  39. Saberi D, Shojaeyan F, Niknam K (2016) Tetrahedron Lett 57:566

    Article  CAS  Google Scholar 

  40. Nuree Y, Singha R, Ghosh M, Roy P, Ray JK (2016) Tetrahedron Lett 57:1479

    Article  CAS  Google Scholar 

  41. Khatun N, Santra SK, Banerjee A, Patel BK (2015) Eur J Org Chem 2015:1309

    Article  CAS  Google Scholar 

  42. Yadav RS, Havlica J, Kuřitka I, Kozakova Z, Palou M, Bartoníčková E, Boháč M, Frajkorová F, Masilko J, Hajdúchová M (2015) J Supercond Nov Magn 28:1417

    Article  CAS  Google Scholar 

  43. Alijani HQ, Pourseyedi S, Torkzadeh-Mahani M, Seifalian A, Khatami M (2020) Artif Cells Nanomed Biotechnol 48:242

    Article  CAS  PubMed  Google Scholar 

  44. Gaspa S, Amura I, Porcheddu A, De Luca L (2017) New J Chem 41:931

    Article  CAS  Google Scholar 

  45. Kader SS, Paul DP, Hoque SM (2014) Int J Mater Mech Manuf 2:5

    CAS  Google Scholar 

  46. Zhu Z, Li X, Zhao Q, Li Y, Sun C, Cao Y (2013) Mater Res Bull 48:2927

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Tarbiat Modares University, Tehran, Iran

    Esmaiel Eidi, Mohamad Z. Kassaee & Zahra Nasresfahani

Authors
  1. Esmaiel Eidi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Mohamad Z. Kassaee
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Zahra Nasresfahani
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mohamad Z. Kassaee.

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 6229 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Eidi, E., Kassaee, M.Z. & Nasresfahani, Z. Efficient synthesis of symmetrical anhydrides by cross dehydrogenative coupling of aryl aldehydes over CuFe2O4 nanoparticles. Monatsh Chem 152, 461–468 (2021). https://doi.org/10.1007/s00706-021-02741-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-021-02741-7

Keywords

Search

Navigation