8
of 9
LI ET AL.
Finally, the possibility of Cu leaching from Cu‐
[8] H. Naeimi, R. Shaabani, Cat. Com. 2016, 87, 6.
Cu O@RGO during the reaction was investigated
[9] J. G. Álvarez, J. Díez, J. Gimeno, F. J. Suárez, C. Vincent, Eur. J.
Inorg. Chem. 2012, 5854.
2
(Table 3). Obviously, there was only 1.7 ppm copper con-
tent after the first cycle and the amount of copper
increased during subsequent recycling. The most amount
of copper leaching was 12.8 ppm after the sixth cycle and
the catalytic activity was slightly decreased in comparison
with the fresh catalyst.
[
[
[
10] S. Q. Bai, L. Jiang, J. L. Zuo, T. S. A. Hor, Dalton Trans. 2013,
42, 11319.
11] H. X. Siyang, H. L. Liu, X. Y. Wu, P. N. Liu, RSC Adv. 2015, 5,
4693.
12] D. C. Marcano, D. V. Kosynkin, J. M. Berlin, A. Sinitskii, Z. Z.
Sun, A. Slesarev, L. B. Alemany, W. Lu, J. M. Tour, ACS Nano
2
010, 4, 4806.
4
| CONCLUSIONS
[
[
13] A. K. Geim, K. S. Novoselov, Nat. Mater. 2007, 6, 183.
14] X. Feng, P. P. Lv, W. Sun, X. Y. Han, L. F. Gao, G. X. Zheng,
Cu–Cu O nanocomposite material on RGO as a green and
efficient catalyst was prepared by a one‐pot reflux synthe-
sis method and characterized using TEM, XRD, FT‐IR,
2
Cat. Com. 2017, 99, 105.
[15] S. Diyarbakir, H. Can, O. Metin, ACS Appl. Mater. Interfaces
015, 7, 3199.
2
XPS and Raman analyses. The Cu–Cu O nanocomposite
2
material exhibited good dispersion on RGO and the aver-
age size of the copper nanoparticles was about 15 nm. The
[16] M. X. Chen, Z. Zhang, L. Z. Li, Y. Liu, W. Wang, J. P. Gao, RSC
Adv. 2014, 4, 30914.
Cu‐Cu O@RGO catalyst was applied to the tandem reac-
[17] W. Fu, Z. Zhang, P. Zhuang, J. Shen, M. Ye, J. Colloid Interface
Sci. 2017, 497, 83.
2
tion of halides and sodium azide with terminal alkynes.
The catalyst was easily recoverable and had very high sta-
bility during the catalytic reaction. Therefore, the work
presented provides a green and efficient tandem method
for the synthesis of 1,2,3‐triazole compounds.
[18] X. N. Guo, C. H. Hao, G. Q. Jin, H. Y. Zhu, X. Y. Guo, Angew.
Chem. Int. Ed. 2014, 53, 1973.
[
[
[
[
[
[
[
[
[
[
19] X. Y. Yan, X. L. Tong, Y. F. Zhang, X. D. Han, Y. Y. Wang, G. Q.
Jin, Y. Qin, X. Y. Guo, Chem. Commun. 2012, 48, 1892.
20] B. J. Jiang, S. Z. Song, J. Q. Wang, Y. Xie, W. Y. Chu, H. F. Li, H.
Xu, C. G. Tian, H. G. Fu, Nano Res. 2014, 7, 1280.
ACKNOWLEDGMENTS
21] H. Y. Zhao, G. J. Mao, H. T. Han, J. Y. Song, Y. Liu, W. Y. Chu,
This study was funded by the Natural Science Foundation
of Heilongjiang Province of China (grant nos. B201207
and B201208).
Z. Z. Sun, RSC Adv. 2016, 6, 41108.
22] H. T. Han, H. Y. Zhao, Y. Liu, Z. F. Li, J. Y. Song, W. Y. Chu, Z.
Z. Sun, RSC Adv. 2017, 7, 3790.
23] Z. F. Li, H. Y. Zhao, H. T. Han, Y. Liu, J. Y. Song, W. H. Guo, W.
Y. Chu, Z. Z. Sun, Tetrahedron Lett. 2017, 58, 3984.
ORCID
24] W. Liu, K. Tang, M. Lin, L. T. June, S. Q. Bai, D. J. Young, X. Li,
Y. Z. Yang, T. S. Hor, Nanoscale 2016, 8, 9521.
25] H. H. Huo, C. Y. Guo, G. L. Li, X. Han, C. L. Xu, RSC Adv. 2014,
4
, 20459.
REFERENCES
26] D. K. Zhang, D. Wei, Z. T. Cui, S. S. Wang, S. Yang, M. H. Cao,
[
[
[
[
[
[
[
1] P. Thirumurugan, D. Matosiuk, K. Jozwiak, Chem. Rev. 2013,
C. W. Hu, Phys. Chem. Chem. Phys. 2014, 16, 25531.
1
13, 4905.
27] J. W. Sun, Y. S. Fu, G. Y. He, X. Q. Sun, X. Wang, Cat. Sci.
Technol. 2014, 4, 1742.
2] D. C. Ebner, J. C. Culhane, T. N. Winkelman, M. D. Haustein, J.
L. Ditty, J. T. Ippoliti, Bioorg. Med. Chem. 2008, 16, 2651.
28] A. A. Dubale, W. N. Su, A. G. Tamirat, C. J. Pan, B. A. Aragaw,
3] H. Nandivada, X. W. Jiang, J. Lahann, Adv. Mater. 2007, 19,
H. M. Chen, C. H. Chen, B. J. Hwang, J. Mater. Chem. A 2014, 2,
2
197.
4] F. Wei, W. Wang, Y. Ma, C. H. Tung, Z. Xu, Chem. Commun.
016, 52, 14188.
5] C. W. Tornøe, C. Christensen, M. Meldal, J. Org. Chem. 2002,
7, 3057.
1
8383.
29] M. Dabiri, M. Kasmaei, P. Salari, S. K. Movahed, RSC Adv. 2016,
, 57019.
30] X. Q. Xiong, H. X. Chen, Z. K. Tang, Y. B. Jiang, RSC Adv. 2014,
, 9830.
[
[
2
6
6
4
6] V. V. Rostovtsev, L. G. Green, V. V. Fokin, K. B. Sharpless,
Angew. Chem. Int. Ed. 2002, 41, 2596.
[31] Z. Zhang, P. Song, J. B. Zhou, Y. Chen, B. J. Lin, Y. Q. Li, Ind.
Eng. Chem. Res. 2016, 55, 12301.
7] Z. Xu, L. L. Han, G. L. Zhuang, J. Bai, D. Sun, Inorg. Chem.
[32] M. Amini, R. Hassandoost, M. Bagherzadeh, S. Gautam, K. H.
2
015, 54, 4737.
Chae, Cat. Com. 2016, 85, 13.