Chinese Journal of Organic Chemistry >
Palladium Nanoparticles Supported on MIL-101 as an Efficient Heterogeneous Catalyst for Selective C2 Arylation of Benzofuran
Received date: 2017-10-10
Revised date: 2017-12-05
Online published: 2017-12-15
Supported by
Project supported by the National Natural Science Foundation of China (No. 21362047), the Social Development Project of Guizhou Province (No. QKHSYZ-2013-3061) and the Science and Technology Foundation of Guizhou Province (No. QKHJZ-2014-2175).
MIL-101 was synthesized by hydrothermal method, and Pd/MIL-101 catalyst was prepared by supporting palladium nanoparticles on metal-organic frameworks MIL-101. The microstructure and features of the catalyst were characterized by X-ray diffraction (XRD), X-ray photoelectron spectroscopy (XPS), scanning electron microscope (SEM), inductive coupled plasma (ICP), high resolution transmission electron microscopy (HRTEM) and N2 adsorption, respectively. The experimental results reveal that the Pd nanoparticles on Pd/MIL-101 range from 1.5 nm to 2.5 nm, and the content of Pd nanoparticles is 1.5%. The catalytic experiments show that Pd/MIL-101 has a high catalytic activity for the C2 arylation of benzofuran. For less active aryl bromides, the reaction gave moderate yields. Moreover, the catalyst could be recycled many times. After 5 runs of catalysis, the catalyst can still maintain high reactivity. This strategy provides a simple, effective method for the synthesis of benzofuran derivatives.
Xu Huan , Zhang Maoyuan , Huang Xiang , Shi Dabin . Palladium Nanoparticles Supported on MIL-101 as an Efficient Heterogeneous Catalyst for Selective C2 Arylation of Benzofuran[J]. Chinese Journal of Organic Chemistry, 2018 , 38(4) : 832 -839 . DOI: 10.6023/cjoc201710012
[1] (a) Schoedel, A.; Li, M.; Li, D.; O'Keeffe, M.; Yaghi, O. M. Chem. Rev. 2016, 116, 12466.
(b) Li, L.; Cao, X.; Huang, R. Chin. J. Chem. 2016, 34, 143.
[2] Kitagawa, S. Chem. Soc. Rev. 2014, 43, 5415.
[3] Zhou, H. C.; Long, J. R.; Yaghi, O. M. Chem. Rev. 2012, 112, 673.
[4] (a) Mlinar, A. N.; Keitz, B. K.; Gygi, D.; Bloch, E. D.; Long, J. R.; Bell, A. T. ACS Catal. 2014, 4, 717.
(b) Li, Y.; Zou, B.; Xiao, A.; Zhang, H. Chin. J. Chem. 2017, 35, 1501.
[5] Wei, Z.; Gu, Z. Y.; Arvapally, R. K.; Chen, Y. P.; Jr, R. N. M.; Ivy, J. F.; Yakovenko, A. A.; Feng, D.; Omary, M. A.; Zhou, H. C. J. Am. Chem. Soc. 2014, 136, 8269.
[6] Ramsahye, N. A.; Balas, F.; Vallet-Regl, M.; Sebban, M.; Taulelle, F.; Ferey, G. J. Am. Chem. Soc. 2008, 130, 6774.
[7] Zhang, X.; Hu, Q.; Xia, T.; Zhang, J.; Yang, Y.; Cui, Y.; Chen, B.; Qian, G. ACS Appl. Mater. Interfaces 2016, 8, 32259.
[8] (a) Zhu, L.; Liu, X. Q.; Jiang, H. L.; Sun, L. B. Chem. Rev. 2017, 117, 8129.
(b) Zhao, R.; Hu, M.; Li, S.; Zhai, Q.; Jiang, Y. Acta Chim. Sinica 2017, 75, 293(in Chinese). (赵睿南, 胡满成, 李淑妮, 翟全国, 蒋育澄, 化学学报, 2017, 75, 293.)
(c) Xu, G.; Gang, F.; Dong, T.; Fu, Y.; Du, Z. Chin. J. Org. Chem. 2016, 36, 1513(in Chinese). (徐光利, 刚芳莉, 董涛生, 傅颖, 杜正银, 有机化学, 2016, 36, 1513.)
[9] Jiang, H. L.; Akita, T.; Ishida, T.; Haruta, M.; Xu, Q. J. Am. Chem. Soc. 2011, 133,1304.
[10] Huang, Y. B.; Liang, J.; Wang, X. S.; Cao, R. Chem. Soc. Rev. 2017, 46, 126.
[11] Liu, H.; Liu, Y.; Li, Y.; Tang, Z.; Jiang, H. J. Phys. Chem. C 2010, 114, 13362.
[12] Dang, T. T.; Zhu, Y.; Ngiam, J. S. Y.; Ghosh, S. C.; Chen, A.; Seayad, A. M. ACS Catal. 2013, 3, 1406.
[13] Othman, N.; Pan, L.; Mejin, M.; Voong, J. C. L.; Chai, H. B.; Pannell, C. M.; Kinghorn, A. D.; Yeo, T. C. J. Nat. Prod. 2016, 79, 784.
[14] Clair, J. J. L.; Rheingold, A. L.; Burkart, M. D. J. Nat. Prod. 2011, 74, 2045.
[15] Boschelli, D. H.; Kramer, J. B.; Khatana, S. S.; Sorenson, R. J.; Connor, D. T.; Ferin, M. A.; Wright, C. D.; Lesch, M. E.; Imre, K. J. Med. Chem. 1995, 38, 4597.
[16] Mei, R. Q.; Wang, Y. H.; Du, G. H.; Liu, G. M.; Zhang, L.; Cheng, Y. X. J. Nat. Prod. 2009, 72, 621.
[17] Chen, C. C.; Chen, Y.; His, Y. T.; Chang, C. S.; Huang, L. F.; Ho, C. T.; Way, T. D.; Kao, J. Y. J. Agric. Food Chem. 2013, 61, 11418.
[18] Ramos, F. A.; Takaishi,Y.; Shirotori, M.; Kawaguchi, Y.; Tsuchiya, K.; Shibata, H.; Higuti, T.; Tadokoro, T.; Takeuchi, M. J. Agric. Food Chem. 2006, 54, 3551.
[19] Yin, S.-C.; Zhou, Q.; Zhao, X.-Y.; Shao, L.-X. J. Org. Chem. 2015, 80, 8916.
[20] Ortega, N.; Urban, S.; Beiring, B.; Glorius, F. Angew. Chem., Int. Ed. 2012, 51, 1710.
[21] Rao, M. L. N.; Awasthi, D. K.; Talode, J. B. Tetrahedron Lett. 2012, 53, 2662.
[22] Salemi, H.; Kaboudin, B.; Kazemia, F.; Yokomatsub, T. RSC Adv. 2016, 6, 52656.
[23] Wang, L.; Yi, W.; Cai, C. Chem. Commun. 2011, 47, 806.
[24] Ferey, G.; Mellot-Draznieks, C.; Serre, C.; Millange, F.; Dutour, J.; Surble, S.; Margiolaki, I. Science 2005, 309, 2040.
[25] Hamon, L.; Serre, C.; Devic, T.; Loiseau, T.; Millange, F.; Ferey, G.; Weireld, G. D. J. Am. Chem. Soc. 2009, 131, 8775.
[26] Lammert, M.; Bernt, S.; Vermoortele, F.; Vos, D. E. D.; Stock, N. Inorg. Chem. 2013, 52, 8521.
[27] Pan, Y.; Yuan, B.; Li, Y.; H, D. Chem. Commun. 2010, 46, 2280.
[28] Bosiak, M. J. ACS Catal. 2016, 6, 2429.
/
| 〈 |
|
〉 |
