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.
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Maiti D (2011) Chem Commun 47:8340–8342
Zhang R, Miao C, Shen Z, Wang S, Xia C, Sun W (2012) ChemCatChem 4:824–830
Kataoka N, Shelby Q, Stambuli JP, Hartwig JF (2002) J Org Chem 67:5553–5566
Anderson KW, Tundel RE, Ikawa T, Altman RA, Buchwald SL (2006) Angew Chem Int Ed 45:6523–6527
Huang Z, Li F, Chen B, Xue F, Chen G, Yuan G (2011) Appl Catal A 403:104–111
Panda N, Jena AK, Mohapatra S, Rout SR (2011) Tetrahedron Lett 52:1924–1927
Taillefer M, Xia N, Ouali A (2007) Angew Chem Int Ed 46:934–936
Zhang R, Miao C, Wang S, Xia C, Sun W (2013) ChemCatChem 5:142–145
Wang Z, Cohen SM (2007) J Am Chem Soc 129:12368–12369
Nguyen JG, Cohen SM (2010) J Am Chem Soc 132:4560–4561
Farha OK, Hupp JT (2010) Acc Chem Res 43:1166–1175
Farha OK, Malliakas CD, Kanatzidis MG, Hupp JT (2010) J Am Chem Soc 132:950–952
Tanabe KK, Cohen SM (2009) Angew Chem Int Ed 48:7424–7427
Bae Y-S, Spokoyny AM, Farha OK, Snurr RQ, Hupp JT, Mirkin CA (2010) Chem Commun 46:3478–3480
Roberts JM, Fini BM, Sarjeant AA, Farha OK, Hupp JT, Scheidt KA (2012) J Am Chem Soc 134:3334–3337
Janssens N, Wee LH, Bajpe S, Breynaert E, Kirschhock CEA, Martens JA (2012) Chem Sci 3:1847–1850
Lili L, Xin Z, Jinsen G, Chunming X (2012) Green Chem 14:1710–1720
Li Z-H, Xue L-P, Wang L, Zhang S-T, Zhao B-T (2012) Inorg Chem Commun 27:119–121
Phan NTS, Nguyen TT, Ho P, Nguyen KD (2013) ChemCatChem 5:1822–1831
Phan NTS, Nguyen TT, Nguyen VT, Nguyen KD (2013) ChemCatChem 5:2374–2381
Tan K, Nijem N, Canepa P, Gong Q, Li J, Thonhauser T, Chabal YJ (2012) Chem Mater 24:3153–3167
Uemura T, Ono Y, Kitagawa K, Kitagawa S (2008) Macromolecules 41:87–94
Cao C, Lu Z, Cai Z, Pang G, Shi Y (2012) Synth Commun 42:279–284
Zhu L, Cheng L, Zhang Y, Xie R, You J (2007) J Org Chem 72:2737–2743
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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
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DOI: https://doi.org/10.1007/s10562-014-1355-9