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could be confined in the zeolite Cu-ZSM-5-M during the crystal-
lization process, and strongly interacted with the negatively charged
framework, resulting in highly active Cu (d o 2) species.
The reusable ability of Cu-ZSM-5-M and Cu-ZSM-5-MI catalysts
in the cross-coupling reaction was also investigated. The yield of the
product decreased from 100 and 77% (Run 1) to 84 and 45% (Run
Q. Shen and J. F. Hartwig, J. Am. Chem. Soc., 2006, 128, 2180;
(
2
c) S. R. Guo, W. M. He, J. N. Xiang and Y. Q. Yuan, Chem. Commun.,
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d+
4
5
(a) O. Baldovino-Pantale ´o n, S. Hern ´a ndez-Ortega and D. Morales-
Morales, Inorg. Chem. Commun., 2005, 8, 955; (b) O. Baldovino-
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8, Table S2, ESI†) for Cu-ZSM-5-M and Cu-ZSM-5-MI catalysts,
(
c) S. Fukuzawa, E. Shimizu, Y. Atsuumi, M. Haga and K. Ogata,
respectively. Importantly, when the deactivated catalysts were
calcined at 500 8C in air for 4 h, the activity was recovered to 93
and 50% (Run 9) for Cu-ZSM-5-M and Cu-ZSM-5-MI catalysts,
respectively. These results demonstrate that the Cu-ZSM-5-M
catalyst has good reusability, which is one of the key features
of the practical application in industry. The ICP analysis shows
that the Cu content in the reused Cu-ZSM-5-M and Cu-ZSM-5-MI
catalysts is 1.2 and 0.8 wt%, while in the as synthesized Cu-ZSM-
Tetrahedron Lett., 2009, 50, 2374; (d) H. F. Wang, L. L. Jiang, T. Chen
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7
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8 H. Sharghi, S. Ebrahimpourmoghaddam and M. M. Doroodmand,
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5-M and Cu-ZSM-5-MI is 1.3 and 1.8 wt%. Clearly, the metal
leaching has not occurred for the Cu-ZSM-5-M catalyst during
the reaction process. Furthermore, the Si/Al ratio for reused and
fresh Cu-ZSM-5-M is 33 and 32, respectively. Obviously, Cu-ZSM-
1
1
5-M possesses good chemical stability, which is very important
for industrial applications in the future. Additionally, the inten-
sity of the XRD diffraction peaks for the reused Cu-ZSM-5-M is 12 (a) B. J. Melde, B. T. Holland, C. F. Blandford and A. Stein, Chem.
Mater., 1999, 11, 3302; (b) C.-K. Chen, Y.-W. Chen, C.-H. Lin, H.-P.
Lin and C.-F. Lee, Chem. Commun., 2010, 46, 282; (c) J. Mondal,
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3 (a) D. W. Breck, Zeolite Molecular Sieves, Structure, Chemistry
and Use, John Wiley & Sons, New York, Londong, Sydney, Toronto,
similar to the fresh catalyst (Fig. 1a), and the textual structure of
the reused Cu-ZSM-5-M has no change (Fig. S7 and Table S1,
ESI†), which demonstrates that the Cu-ZSM-5-M catalyst has
good mechanical stability.
1
1
In summary, Cu-ZSM-5-M with a micro-meso-macroporous
structure was synthesized by using a mesoscale surfactant as a
template, which was investigated for catalyzing the synthesis of
diaryl thioethers through cross-coupling of aryl halides with
disulfides. A variety of functional groups on both the aryl halide and
disulphide substrates are well tolerated. Compared with micro-
porous Cu-ZSM-5 and Cu-ZSM-5-MI catalysts, the Cu-ZSM-5-M
catalyst shows high activity and excellent reusability in the cross-
coupling reaction. This is attributed to the fact that the highly
1974; (b) A. Corma, Chem. Rev., 1997, 97, 2373; (c) C. Jo, K. Cho,
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1
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d+
dispersed Cu (d o 2) confined in the framework present high
activity, and the meso-macroporosity in the Cu-ZSM-5-M catalyst
facilitates mass transfer thereby improving its catalytic performance.
We are grateful to the support of this work from the National
Natural Science Foundation of China (U1463203 and 21476030),
the Natural Science Foundation of Zhejiang Province of China
1
6 (a) X. X. Zhou, H. R. Chen, X. Z. Cui, Z. L. Hua, Y. Chen, Y. Zhu,
Y. D. Song, Y. Gong and J. L. Shi, Appl. Catal., A, 2013, 451, 112;
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b) F. Bin, C. L. Song, G. Lv, J. N. Song, S. H. Wu and X. D. Li, Appl.
(Z14B060012). The authors thank the anonymous reviewers for
Catal., B, 2014, 150–151, 532; (c) F. Bin, X. L. Wei, B. Li and K. S. Hui,
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their invaluable advice.
1
7 C. G. Bates, R. K. Gujadhur and D. Venkataraman, Org. Lett., 2002,
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