Citation: Feng Cuilan, Hei Liying, Li Zhen, Liu Lantao. Magnetic Microporous Organic Polymer of 1, 1'-Bi-2-naphtholSupported Palladium for Suzuki Coupling Reactions[J]. Chinese Journal of Organic Chemistry, ;2015, 36(1): 179-184. doi: 10.6023/cjoc201507028 shu

Magnetic Microporous Organic Polymer of 1, 1'-Bi-2-naphtholSupported Palladium for Suzuki Coupling Reactions

1.
College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000

Corresponding author: Feng Cuilan, Liu Lantao, liult05@iccas.ac.cn
Received Date: 23 July 2015
Revised Date: 22 August 2015

Fund Project: the National Natural Science Foundation of China 21102087the National Natural Science Foundation of China 21202095

Figures(5)

A recyclable palladium catalyst supported on magnetic microporous organic polymer (MOP) of 1, 1'-bi-2-naphthol (Fe₃O₄@MOPB-Pd) was synthesized by two steps. After being charactered by transmission electron microscope (TEM), X-ray photoelectron spectroscopy (XPS), thermogravimetric analysis (TG) and vibrating sample magnetometer (VSM), the palladium catalyst was applied in Suzuki coupling reaction in air atmosphere. With 0.01 g of Fe₃O₄@MOPB-Pd (0.12 mol% Pd based on bromobenzene) as catalyst, 1.0 mmol of bromobenzene reacted with 1.1 equiv. phenylboronic acid at 60 ℃ for 3 h can give the product with 98% yield. In addition, Fe₃O₄@MOPB-Pd can be easily separated from reaction system in the presence of magnetic field and the 92% yield was achieved even being used at 7th time for the Suzuki coupling reaction of iodobenzene and phenylboronic acid.
- magnetic nanoparticles,
- supported Pd catalyst,
- suzuki coupling reaction,
- BINOL,
- MOPs
1. [1]
2. [2]
3. [3]
  Jiang, J. X.; Wang, C.; Laybourn, A.; Hasell, T.; Clowes, R.; Khimyak, Y. Z.; Xiao, J.; Higgins, S. J.; . Adams, D. J.; Cooper, A. I. Angew. Chem., Int. Ed. 2011, 50, 1072.
  (b) Du, X.; Sun, Y.; Tan, B.; Teng, Q.; Yao, X.; Su, C.; Wang, W. Chem. Commun. 2010, 46, 970.
  (c) Totten, R. K.; Weston, M. H.; Park, J. K.; Farha, O. K.; Hupp, J. T.; Nguyen. S. T. ACS Catal. 2013, 3, 1454.
  (d) Wang, J. L.; Wang, C.; de Krafft K. E.; Lin, W. B. ACS Catal. 2012, 2, 417.
  (e) Totten, R. K.; Kim, Y. S.; Weston, M. H.; Farha, O. K.; Hupp J. T.; Nguyen, S. T. J. Am. Chem. Soc. 2013, 135, 11720.
  f) Wang, W.; Zheng, A.; Zhao, P.; Xia C.; Li, F. ACS Catal. 2014, 4, 321
  (g) Kraft, S. J.; Zhang, G.; Childers, D.; Dogan, F.; Miller, J. T.; Nguyen S. T.; Hock, A. S. Organometallics 2014, 33, 2517
4. [4]
  Rangel Rangel, E.; Maya, E. M.; Sánchez, F.; de la Campaa J. G.; Iglesias, M. Green Chem. 2015, 17, 466.
  (b) Pachfule, P.; Panda, M. K.; Kandambeth, S.; Shivaprasad, S. M.; Díaz Díaz, D.; Banerjee, R. J. Mater. Chem. A 2014, 2, 7944.
  (c) Ding, S.; Gao, J.; Wang, Q.; Zhang, Y.; Song, W.; Su, C.; Wang, W. J. Am. Chem. Soc. 2011, 133, 19816.
  (d) Li, B.; Guan, Z.; Yang, X.; Wang, W. D.; Wang, W.; Hussain, I.; Song, K.; Tan, B.; Li, T. J. Mater. Chem. A 2014, 2, 11930.
  (e) Li, L.; Zhao, H.; Wang, R. ACS Catal. 2015, 5, 948.
  (f) Shunmughanathan, M.; Puthiaraj, P.; Pitchumani, K. ChemCatChem 2015, 7, 666.
5. [5]
  Nasir Baig, R. B.; Varma, R. S. Chem. Commun. 2013, 49, 752.
  (b) Wang, D.; Astruc, D. Chem. Rev. 2014, 114, 6949.
  (c) Gawande, M. B.; Brancoa, P. S.; Varma, R. S. Chem. Soc. Rev. 2013, 42, 3371.
  (d) Shylesh, S.; Schünemann, V.; Thiel, W. R. Angew. Chem., Int. Ed. 2010, 49, 3428.
  (e) Polshettiwar, V.; Luque, R.; Fihri, A.; Zhu, H.; Bouhrara M.; Basset, J. M. Chem. Rev. 2011, 111, 3036.
6. [6]
  Kainz, Q. M.; Reiser, O. Acc. Chem. Res. 2014, 47: 667. doi: 10.1021/ar400236y
7. [7]
  Yang, X.; Li, B.; Majeed, I.; Liang, L.; Long, X.; Tan, B. Polym. Chem. 2013, 4, 1425.
  (b) Yoo, J.; Park, N.; Park, J. H.; Park, J. H.; Kang, S.; Lee, S. M.; Kim, H. J.; Jo, H.; Park, J. G.; Son, S. U. ACS Catal. 2015, 5, 350.
  (c) Yang, J.; Wang, D.; Liu, W.; Zhang, X.; Bian, F.; Yu, W. Green Chem. 2013, 15, 3429.
8. [8]
  Li, B.; Gong, R.; Wang, W.; Huang, X.; Zhang, W.; Li, H.; Hu, C.; Tan, B. Macromolecules 2011, 44, 2410. doi: 10.1021/ma200630s
9. [9]
  Li, B.; Guan, Z.; Wang, W.; Yang, X.; Hu, J.; Tan, B.; Li, T. Adv. Mater. 2012, 24, 3390. doi: 10.1002/adma.v24.25
10. [10]
  Luo, Y.; Li, B.; Wang, W.; Wu, K.; Tan, B. Adv. Mater. 2012, 24, 5703. doi: 10.1002/adma.v24.42
11. [11]
  Dawson, R.; Stevens, L. A.; Drage, T. C.; Snape, C. E.; Smith, M. W.; Adams, D. J.; Cooper, A. I. J. Am. Chem. Soc. 2012, 134, 10741. doi: 10.1021/ja301926h
12. [12]
  Hei, L.; Feng C.; Li, Z.; Liu, L.; Gui, J. Chin. J. Org. Chem. 2015, 35, 1673 (in Chinese). doi: 10.6023/cjoc201503014
13. [13]
  Soomro, S. S.; Ansari, F. L.; Chatziapostolou, K.; Köhler, K. J. Catal. 2010, 273, 138. doi: 10.1016/j.jcat.2010.05.007
14. [14]
  Ouyang, K.; Xi, Z. Acta Chim. Sinica 2013, 71, 13 (in Chinese). doi: 10.6023/A12110984
15. [15]
  Jadsada, R.; Thanawat, C.; Songyos, P.; Sirilata, Y.; Preeyanuch, S.; Pailin, S.; Palangpon, K.; Supavadee K. J. Organomet. Chem. 2014, 752, 161. doi: 10.1016/j.jorganchem.2013.12.015
16. [16]
  Wan, L.; Cai, C. Catal. Commun. 2012, 24, 105. doi: 10.1016/j.catcom.2012.03.032
17. [17]
  Freundlich, J. S.; Landis, H. E. Tetrahedron Lett. 2006, 47, 4275. doi: 10.1016/j.tetlet.2006.04.027
18. [18]
  Mandali, P. K, ; Chand, D. K. Catal. Commun. 2013, 31, 16. doi: 10.1016/j.catcom.2012.10.020
19. [19]
  Chua, Y. Y.; Duong, H. A. Chem. Commun. 2014, 50, 8424. doi: 10.1039/c4cc02930e
20. [20]
  Liu, C.; Ni, Q. J.; Hu, P. P.; Qiu, J. S. Org. Biomol. Chem. 2011, 9, 1054. doi: 10.1039/C0OB00524J
21. [21]
  Feng, G. F.; Liu, F. J.; Lin, C.; Li, W. T.; Wang, S. N.; Qi, C. Z. Catal. Commun. 2013, 37, 27. doi: 10.1016/j.catcom.2013.03.006
22. [22]
  Haga, N.; Takayanagi, H. J. Org. Chem. 1996, 61, 735. doi: 10.1021/jo9517196
23. [23]
  ] Cella, R.; Cunha, R. L. O. R.; Reis, A. E. S.; Pimenta, D. C.; Klitzke, C. F.; Stefani, H. A. J. Org. Chem. 2006, 71, 244. doi: 10.1021/jo052061r
24. [24]
  Kabalka, G. W.; Al-Masum, M. Tetrahedron Lett. 2005, 46, 6329. doi: 10.1016/j.tetlet.2005.07.036
25. [25]
  Le, X. D.; Dong, Z. P.; Jin, Z. C.; Wang, Q. Q.; Ma, J. T. Catal. Commun. 2014, 53, 47. doi: 10.1016/j.catcom.2014.04.025
1. [1]
  Senqiang Zhu , Ruohan Li , Yujia Yang , Jinzhi Liao , Rui Liu . 聚光成辉——Suzuki偶联反应高效制备聚集诱导发射荧光分子及其潜指纹识别应用. University Chemistry, 2026, 41(5): 109-119. doi: 10.12461/PKU.DXHX202511066
2. [2]
  Wen WANG , Ying XU , Gang XIONG , Lixin YOU , Yaguang SUN . Pd-NHC-functionalized La-metal-organic framework for efficient Suzuki-Miyaura cross-coupling reaction. Chinese Journal of Inorganic Chemistry, 2026, 42(7): 1475-1484. doi: 10.11862/CJIC.20260025
3. [3]
  Gaopeng Liu , Lina Li , Bin Wang , Ningjie Shan , Jintao Dong , Mengxia Ji , Wenshuai Zhu , Paul K. Chu , Jiexiang Xia , Huaming Li . Construction of Bi Nanoparticles Loaded BiOCl Nanosheets Ohmic Junction for Photocatalytic CO₂ Reduction. Acta Physico-Chimica Sinica, 2024, 40(7): 2306041-0. doi: 10.3866/PKU.WHXB202306041
4. [4]
  Qiangqiang SUN , Pengcheng ZHAO , Ruoyu WU , Baoyue CAO . Multistage microporous bifunctional catalyst constructed by P-doped nickel-based sulfide ultra-thin nanosheets for energy-efficient hydrogen production from water electrolysis. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1151-1161. doi: 10.11862/CJIC.20230454
5. [5]
  Tianhao GE , Sirong LU , Zhiyin XIAO , Wei ZHONG . Synthesis of porphyrin-based ionic polymeric materials for catalytic application in CO₂ conversion. Chinese Journal of Inorganic Chemistry, 2026, 42(4): 722-736. doi: 10.11862/CJIC.20250312
6. [6]
  Fanpeng Meng , Fei Zhao , Jingkai Lin , Jinsheng Zhao , Huayang Zhang , Shaobin Wang . Optimizing interfacial electric fields in carbon nitride nanosheet/spherical conjugated polymer S-scheme heterojunction for hydrogen evolution. Acta Physico-Chimica Sinica, 2025, 41(8): 100095-0. doi: 10.1016/j.actphy.2025.100095
7. [7]
  Haoyu Sun , Dun Li , Yuanyuan Min , Yingying Wang , Yanyun Ma , Yiqun Zheng , Hongwen Huang . Hierarchical Palladium-Copper-Silver Porous Nanoflowers as Efficient Electrocatalysts for CO₂ Reduction to C₂₊ Products. Acta Physico-Chimica Sinica, 2024, 40(6): 2307007-0. doi: 10.3866/PKU.WHXB202307007
8. [8]
  Kezhen Qi , Bei Cheng , Kaiqiang Xu . Ultrafast interfacial charge transfer promoted by the LSPR of Au nanoparticles for photocatalytic H₂ evolution. Acta Physico-Chimica Sinica, 2026, 42(3): 100205-0. doi: 10.1016/j.actphy.2025.100205
9. [9]
  Haiqiang Lin , Weizheng Weng , Jingdong Lin , Mingshu Chen , Xueming Fang , Lefu Yang . Diverse Variables-Driven Catalytic Optimization: Experimental Enhancement and Instructional Design for Selective Methane Oxidation on Supported Nickel-based Catalysts. University Chemistry, 2025, 40(11): 327-336. doi: 10.12461/PKU.DXHX202505106
10. [10]
  Xinyi MA , Yuhang XIAO , Qian LI , Zihuan YAN , Chengyan LIU , Xiguang GAO , Hongju YIN , Feixiang CHENG . Thienyl metal coordination polymers: Preparation and photocatalytic degradation performance of phenol. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 969-979. doi: 10.11862/CJIC.20250317
11. [11]
  Hailang JIA , Hongcheng LI , Pengcheng JI , Yang TENG , Mingyun GUAN . Preparation and performance of N-doped carbon nanotubes composite Co₃O₄ as oxygen reduction reaction electrocatalysts. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 693-700. doi: 10.11862/CJIC.20230402
12. [12]
  Yan LI , Gongxuan LÜ . Au and Pt-loaded nickel-iron layered hydroxide dual-site catalyst for efficient hydrogen production from water electrolysis. Chinese Journal of Inorganic Chemistry, 2026, 42(7): 1463-1474. doi: 10.11862/CJIC.20260032
13. [13]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
14. [14]
  Bing WEI , Jianfan ZHANG , Zhe CHEN . Research progress in fine tuning of bimetallic nanocatalysts for electrocatalytic carbon dioxide reduction. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 425-439. doi: 10.11862/CJIC.20240201
15. [15]
  Junjie Zhang , Yue Wang , Qiuhan Wu , Ruquan Shen , Han Liu , Xinhua Duan . Preparation and Selective Separation of Lightweight Magnetic Molecularly Imprinted Polymers for Trace Tetracycline Detection in Milk. University Chemistry, 2024, 39(5): 251-257. doi: 10.3866/PKU.DXHX202311084
16. [16]
  Botao QU , Qian WANG , Qian WANG , Ruiping ZHANG . Synthesis, crystal structures, and luminescence properties of zinc coordination polymers based on 2,5-dibromoterephthalate. Chinese Journal of Inorganic Chemistry, 2026, 42(5): 917-924. doi: 10.11862/CJIC.20260357
17. [17]
  Wei Sun , Yongjing Wang , Kun Xiang , Saishuai Bai , Haitao Wang , Jing Zou , Arramel , Jizhou Jiang . CoP Decorated on Ti₃C₂T_x MXene Nanocomposites as Robust Electrocatalyst for Hydrogen Evolution Reaction. Acta Physico-Chimica Sinica, 2024, 40(8): 2308015-0. doi: 10.3866/PKU.WHXB202308015
18. [18]
  Tong TAO , Shufeng ZHANG , Feifan LANG , Chunyan NI , Bing WU , Jianping LANG . Synthesis, structures, and daylight-induced [2+2] cycloaddition reactivity of two Cd(Ⅱ)-based pillared-layer coordination polymers. Chinese Journal of Inorganic Chemistry, 2026, 42(6): 1121-1130. doi: 10.11862/CJIC.20260115
19. [19]
  Yuanpei ZHANG , Jiahong WANG , Jinming HUANG , Zhi HU . Preparation of magnetic mesoporous carbon loaded nano zero-valent iron for removal of Cr(Ⅲ) organic complexes from high-salt wastewater. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1731-1742. doi: 10.11862/CJIC.20240077
20. [20]
  Hanmei Lü , Xin Chen , Qifu Sun , Ning Zhao , Xiangxin Guo . Uniform Garnet Nanoparticle Dispersion in Composite Polymer Electrolytes. Acta Physico-Chimica Sinica, 2024, 40(3): 2305016-0. doi: 10.3866/PKU.WHXB202305016

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(1887)
HTML views(232)

通讯作者: 陈斌, bchen63@163.com

1.
沈阳化工大学材料科学与工程学院沈阳 110142