Cu2O/SiC as efficient catalyst for Ullmann coupling of phenols with aryl halides

doi:10.1016/S1872-2067(17)62785-2

Abstract

Abstract:

ACu₂O/SiC heterogeneous catalyst was prepared via a two-step liquid-phase method using diethylene glycol as both the solvent and the reducing agent. The catalyst was characterized using X-ray diffraction, X-ray photoelectron spectroscopy, scanning electron microscopy (SEM), transmission electron microscopy (TEM), and H₂ temperature-programmed reduction. All the results indicate that Cu is present on the SiC support primarily as Cu₂O. The SEM and TEM results show that cubic Cu₂O nanoparticles are uniformly dispersed on the β-SiC surface. The reaction conditions, namely the temperature, reaction time, and amounts of base and catalyst used, for the Ullmann-type C-O cross-coupling reaction were optimized. A model reaction was performed using iodobenzene (14.0 mmol) and phenol (14.0 mmol) with Cu₂O/SiC (5 wt% Cu) as the catalyst, Cs₂CO₃ (1.0 equiv.) as the base, and tetrahydrofuran as the solvent at 150℃ for 3 h; a yield of 97% was obtained and the turnover frequency (TOF) was 1136 h^-1. The Cu₂O/SiC catalyst has a broad substrate scope and can be used in Ullmann-type C-O cross-coupling reactions of aryl halides and phenols bearing a variety of different substituents. The catalyst also showed high activity in the Ullmann-type C-S cross-coupling of thiophenol with iodobenzene and substituted iodobenzenes; a TOF of 1186 h^-1 was achieved. The recyclability of the Cu₂O/SiC catalyst in the O-arylation of phenol with iodobenzene was investigated under the optimum conditions. The yield decreased from 97% to 64% after five cycles. The main reason for the decrease in the catalyst activity is loss of the active component, i.e., Cu₂O.

Key words: Cuprous oxide, Silica carbide, Ullmann coupling, O-arylation, Phenols, Aryl halide

Yibing Wang, Xiaoning Guo, Manqian Lü, Zhaoyang Zhai, Yingyong Wang, Xiangyun Guo. Cu₂O/SiC as efficient catalyst for Ullmann coupling of phenols with aryl halides[J]. Chinese Journal of Catalysis, 2017, 38(4): 658-664.

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References

[1] F. Theil, Angew. Chem. Int. Ed., 1999, 38, 2345-2347.
[2] F. Ullmann, Ber. Dtsch. Chem. Ges., 1904, 37, 853-854.
[3] M. Palucki, J. P. Wolfe, S. L. Buchwald, J. Am. Chem. Soc., 1997, 119, 3395-3396.
[4] J. F. Marcoux, S. Doye, S. L. Buchwald, J. Am. Chem. Soc., 1997, 119, 10539-10540.
[5] G. Mann, C. Incarvito, A. L. Rheingold, J. F. Hartwig, J. Am. Chem. Soc., 1999, 121, 3224-3225.
[6] R. Hosseinzadeh, M. Tajbakhsh, M. Mohadjerani, M. Alikarami, Synlett, 2005, 1101-1104.
[7] N. Xia, M. Taillefer, Chem. Eur. J., 2008, 14, 6037-6039.
[8] F. Monnier, M. Taillefer, Angew. Chem. Int. Ed., 2009, 48, 6954- 6971.
[9] M. Kidwai, N. K. Mishra, V. Bansal, A. Kumar, S. Mozumdar, Tetrahedron Lett., 2007, 48, 8883-8887.
[10] H. Q. Li, C. P. Li, J. Bai, C. L. Zhang, W. Y. Sun, RSC Adv., 2014, 4, 48362-48367.
[11] P. Puthiaraj, W. S. Ahn, Catal. Sci. Technol., 2016, 6, 1701-1709.
[12] J. T. Zhang, Z. H. Zhang, Y. Wang, X. Q. Zheng, Z. Y. Wang, Eur. J. Org. Chem., 2008, 5112-5116.
[13] D. Saberi, M. Sheykhan, K. Niknam, A. Heydari, Catal. Sci. Technol., 2013, 3, 2025-2031.
[14] J. Y. Kim, J. C. Park, A. Kim, A. Y. Kim, H. J. Lee, H. Song, K. H. Park, Eur. J. Inorg. Chem., 2009, 4219-4223.
[15] 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, 1892-1894.
[16] Z. Y. Zhai, X. N. Guo, Z. F. Jiao, G. Q. Jin, X. Y. Guo, Catal. Sci. Technol., 2014, 4, 4196-4199.
[17] M. J. Ledoux, C. Pham-Huu, CATTECH, 2001, 5, 226-246.
[18] Y. F. Liu, O. Ersen. C. Meny, F. Luck, C. Pham-Huu, ChemSusChem, 2014, 7, 1218-1239.
[19] Z. F. Jiao, Z. Y. Zhai, X. N. Guo, X. Y. Guo, J. Phys. Chem. C, 2015, 119, 3238-3243.
[20] Y. L. Cui, X. N. Guo, Y. Y. Wang, X. Y. Guo, Chin. J. Catal., 2015, 36, 322-327.
[21] C. H. Hao, X. N. Guo, Y. T. Pan, S. Chen, Z. F. Jiao, H. Yang, X. Y. Guo, J. Am. Chem. Soc., 2016, 138, 9361-9364.
[22] H. L. Li, Y. G. Lei, Y. Huang, Y. P. Fang, Y. H. Xu, L. Zhu, X. Li, J. Nat. Gas Chem., 2011, 20, 145-150.
[23] G. Q. Jin, X. Y. Guo, Microporous Mesoporous Mater., 2003, 60, 207-212.
[24] J. Y. Hao, Y. Y. Wang, X. L. Tong, G. Q. Jin, X. Y. Guo, Int. J. Hydrogen Energy, 2012, 37, 15038-15044.
[25] M. A. Bhosale, B. M. Bhanage, Adv. Powder Technol., 2016, 27, 238-244.
[26] H. Zhu, M. L. Du, D. L. Yu, Y. Wang, L. N. Wang, M. L. Zou, M. Zhang, Y. Q. Fu, J. Mater. Chem. A, 2013, 1, 919-929.
[27] H. Azimi, S. Kuhri, A. Osvet, G. Matt, L. S. Khanzada, M. Lemmer, N. A. Luechinger, M. I. Larsson, E. Zeira, D. M. Guldi, C. J. Brabec, J. Am. Chem. Soc., 2014, 136, 7233-7236.
[28] X. W. Liu, F. Y. Wang, F. Zhen, J. R. Huang, RSC Adv., 2012, 2, 7647-7651.
[29] J. Pal, M. Ganguly, S. Dutta, C. Mondal, Y. Negishi, T. Pal, CrystEngComm, 2014, 16, 883-893.
[30] C. S. Polster, H. Nair, C. D. Baertsch, J. Catal., 2009, 266, 308-319.
[31] J. D. Hong, X. Y. Xia, Y. S. Wang, R. Xu, J. Mater. Chem., 2012, 22, 15006-15012.
[32] C. Liu, B. Q. Wang, T. Liu, P. Sun, Y. Gao, F. M. Liu, G. Y. Lu, Sens. Actuator B, 2016, 235, 294-301.

Cu₂O/SiC as efficient catalyst for Ullmann coupling of phenols with aryl halides

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