Skip to main content
Log in

A Metal–Organic Framework Cu2(BDC)2(DABCO) as an Efficient and Reusable Catalyst for Ullmann-Type N-Arylation of Imidazoles

  • Published:
Catalysis Letters Aims and scope Submit manuscript

Abstract

A highly porous metal–organic framework (Cu2(BDC)2(DABCO)) was synthesized and used as an efficient and recyclable heterogeneous catalyst for the Ullmann-type N-arylation of aryl halides with imidazoles. The Cu2(BDC)2(DABCO) was characterized by several techniques, including X-ray powder diffraction, scanning electron microscopy, transmission electron microscopy, thermogravimetric analysis, Fourier transform infrared, atomic absorption spectrophotometry, and nitrogen physisorption measurements. The catalyst offered high activity under mild conditions, confirming outstanding advantages when employing the Cu2(BDC)2(DABCO) as catalyst for Ullmann-type N-arylation reaction. The catalyst could be separated from the reaction mixture by simple filtration, and could be reused without a significant degradation 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.

Fig. 1
Fig. 2
Scheme 1
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Maiti D (2011) Chem Commun 47:8340–8342

    Article  CAS  Google Scholar 

  2. Zhang R, Miao C, Shen Z, Wang S, Xia C, Sun W (2012) ChemCatChem 4:824–830

    Article  CAS  Google Scholar 

  3. Kataoka N, Shelby Q, Stambuli JP, Hartwig JF (2002) J Org Chem 67:5553–5566

    Article  CAS  Google Scholar 

  4. Anderson KW, Tundel RE, Ikawa T, Altman RA, Buchwald SL (2006) Angew Chem Int Ed 45:6523–6527

    Article  CAS  Google Scholar 

  5. Huang Z, Li F, Chen B, Xue F, Chen G, Yuan G (2011) Appl Catal A 403:104–111

    Article  CAS  Google Scholar 

  6. Panda N, Jena AK, Mohapatra S, Rout SR (2011) Tetrahedron Lett 52:1924–1927

    Article  CAS  Google Scholar 

  7. Taillefer M, Xia N, Ouali A (2007) Angew Chem Int Ed 46:934–936

    Article  CAS  Google Scholar 

  8. Zhang R, Miao C, Wang S, Xia C, Sun W (2013) ChemCatChem 5:142–145

    Article  CAS  Google Scholar 

  9. Wang Z, Cohen SM (2007) J Am Chem Soc 129:12368–12369

    Article  CAS  Google Scholar 

  10. Nguyen JG, Cohen SM (2010) J Am Chem Soc 132:4560–4561

    Article  CAS  Google Scholar 

  11. Farha OK, Hupp JT (2010) Acc Chem Res 43:1166–1175

    Article  CAS  Google Scholar 

  12. Farha OK, Malliakas CD, Kanatzidis MG, Hupp JT (2010) J Am Chem Soc 132:950–952

    Article  CAS  Google Scholar 

  13. Tanabe KK, Cohen SM (2009) Angew Chem Int Ed 48:7424–7427

    Article  CAS  Google Scholar 

  14. Bae Y-S, Spokoyny AM, Farha OK, Snurr RQ, Hupp JT, Mirkin CA (2010) Chem Commun 46:3478–3480

    Article  CAS  Google Scholar 

  15. Roberts JM, Fini BM, Sarjeant AA, Farha OK, Hupp JT, Scheidt KA (2012) J Am Chem Soc 134:3334–3337

    Article  CAS  Google Scholar 

  16. Janssens N, Wee LH, Bajpe S, Breynaert E, Kirschhock CEA, Martens JA (2012) Chem Sci 3:1847–1850

    Article  CAS  Google Scholar 

  17. Lili L, Xin Z, Jinsen G, Chunming X (2012) Green Chem 14:1710–1720

    Article  Google Scholar 

  18. Li Z-H, Xue L-P, Wang L, Zhang S-T, Zhao B-T (2012) Inorg Chem Commun 27:119–121

    Article  CAS  Google Scholar 

  19. Phan NTS, Nguyen TT, Ho P, Nguyen KD (2013) ChemCatChem 5:1822–1831

    Article  CAS  Google Scholar 

  20. Phan NTS, Nguyen TT, Nguyen VT, Nguyen KD (2013) ChemCatChem 5:2374–2381

  21. Tan K, Nijem N, Canepa P, Gong Q, Li J, Thonhauser T, Chabal YJ (2012) Chem Mater 24:3153–3167

    Article  CAS  Google Scholar 

  22. Uemura T, Ono Y, Kitagawa K, Kitagawa S (2008) Macromolecules 41:87–94

    Article  CAS  Google Scholar 

  23. Cao C, Lu Z, Cai Z, Pang G, Shi Y (2012) Synth Commun 42:279–284

    Article  CAS  Google Scholar 

  24. Zhu L, Cheng L, Zhang Y, Xie R, You J (2007) J Org Chem 72:2737–2743

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Tung T. Nguyen.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1745 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Nguyen, T.T., Phan, N.T.S. A Metal–Organic Framework Cu2(BDC)2(DABCO) as an Efficient and Reusable Catalyst for Ullmann-Type N-Arylation of Imidazoles. Catal Lett 144, 1877–1883 (2014). https://doi.org/10.1007/s10562-014-1355-9

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10562-014-1355-9

Keywords

Navigation