Citation: Li Zhang, Wen-Huan Dong, Ning-Zhao Shang, Cheng Feng, Shu-Tao Gao, Chun Wang. N-Doped porous carbon supported palladium nanoparticles as a highly efficient and recyclable catalyst for the Suzuki coupling reaction[J]. Chinese Chemical Letters, ;2016, 27(01): 149-154. doi: 10.1016/j.cclet.2015.08.007 shu

N-Doped porous carbon supported palladium nanoparticles as a highly efficient and recyclable catalyst for the Suzuki coupling reaction

1.
College of Science, Agricultural University of Hebei, Baoding 071001, China

Corresponding author: Shu-Tao Gao, Chun Wang,
Received Date: 25 May 2015
Available Online: 16 July 2015
Fund Project: This work was financially supported by the National Natural Science Foundation of China(Nos. 31171698, 31471643) (Nos. 31171698, 31471643) the Innovation Research Program of Department of Education of Hebei for Hebei Provincial Universities(No. LJRC009) (No. LJRC009) Natural Science Foundation of Hebei Province(No. B2015204003) (No. B2015204003)the Natural Science Foundation of Agricultural University of Hebei(Nos. LG201404, ZD201506). (Nos. LG201404, ZD201506)

A new catalyst, Pd particles supported on the N-doped porous carbon(PC) derived from Zn-based metal-organic frameworks(zeolitic imidazolate framework:ZIF-8), was successfully prepared for the first time. The as-prepared catalyst was designated as N-doped PC-Pd, and characterized by X-ray diffraction, X-ray photoelectron spectroscopy, transmission electron microscopy, scanning electron microscope, N2 adsorption and inductively coupled plasma atomic emission spectroscopy. The N-doped PC-Pd composite exhibited high catalytic activity toward the Suzuki-Miyaura cross-coupling reactions. The yields of the products were in the range of 90%-99%. The catalyst could be readily recycled and reused at least 6 consecutive cycles without a significant loss of its catalytic activity.
- Suzuki-Miyaura coupling reaction,
- Pd catalyst,
- N-Doped nanoporous carbon,
- Metal-organic frameworks
1. [1]
  [1] M.B. Thathagar, J. Beckers, G. Rothenberg, Copper-catalyzed suzuki cross-coupling using mixed nanocluster catalysts, J. Am. Chem. Soc. 124(2002) 11858-11859.
2. [2]
  [2] N.Z. Shang, C. Feng, H.Y. Zhang, et al., Suzuki-Miyaura reaction catalyzed by graphene oxide supported palladium nanoparticles, Catal. Commun. 40(2013) 111-115.
3. [3]
  [3] Y.Y. Ma, X.B. Ma, Q. Wang, J.Q. Zhou, Homogenization of inorganic materialsupported palladium catalysts in Suzuki coupling reaction at room temperature, Catal. Sci. Technol. 2(2012) 1879.
4. [4]
  [4] A.R. Siamaki, A.E.R.S. Khder, V. Abdelsayed, M.S. El-Shall, B.F. Gupton, Microwaveassisted synthesis of palladium nanoparticles supported on graphene:a highly active and recyclable catalyst for carbon-carbon cross-coupling reactions, J. Catal. 279(2011) 1-11.
5. [5]
  [5] M. Amini, A. Tarassoli, S. Yousefi, et al., Suzuki-Miyaura cross-coupling reactions in water using in situ generated palladium(Ⅱ)-phosphazane complexes, Chin. Chem. Lett. 25(2014) 166-168.
6. [6]
  [6] H. Cheng, Q.Y. Wu, F. Han, G.F. Yang, Efficient synthesis of 4-substituted pyrazole via microwave-promoted Suzuki cross-coupling reaction, Chin. Chem. Lett. 25(2014) 705-709.
7. [7]
  [7] C.M. Chen, L.Y. Wei, X.H. Guo, S.X. Guo, G. Yan, Investigation of heavy oil refinery wastewater treatment by integrated ozone and activated carbon-supported manganese oxides, Fuel Process. Technol. 124(2014) 165-173.
8. [8]
  [8] L.J. Wang, Q. Han, D.C. Li, et al., Comparisons of Pt catalysts supported on active carbon, carbon molecular sieve, carbon nanotubes and graphite for HI decomposition at different temperature, J. Hydrogen Energy 38(2013) 109-116.
9. [9]
  [9] H. Veisi, R. Masti, D. Kordestani, M. Safaei, O. Sahin, Functionalization of fullerene(C₆₀) with metformine to immobilized palladium as a novel heterogeneous and reusable nanocatalyst in the Suzuki-Miyaura coupling reaction at room temperature, J. Mol. Catal. A:Chem. 385(2014) 61-67.
10. [10]
  [10] H. Veisi, A. Khazaei, M. Safaei, D. Kordestani, Synthesis of biguanide-functionalized single-walled carbon nanotubes(SWCNTs) hybrid materials to immobilized palladium as new recyclable heterogeneous nanocatalyst for Suzuki-Miyaura coupling reaction, J. Mol. Catal. A:Chem. 382(2014) 106-113.
11. [11]
  [11] J.F. Hu, Y.P. Wang, M. Han, et al., A facile preparation of palladium nanoparticles supported on magnetite/s-graphene and their catalytic application in Suzuki-Miyaura reaction, Catal. Sci. Technol. 2(2012) 2332-2340.
12. [12]
  [12] Q. Xu, J.K. Sun, Functional materials derived from open framework templates/precursors:synthesis and applications, Energy Environ. 7(2014) 2071-2100.
13. [13]
  [13] M. Bakherad, S. Jajarmi, A dithizone-functionalized polystyrene resin-supported Pd(Ⅱ) complex as an effective catalyst for Suzuki, Heck, and copper-free Sonogashira reactions under aerobic conditions in water, J. Mol. Catal. A:Chem. 370(2013) 152-159.
14. [14]
  [14] X. Xu, Y. Li, Y.T. Gong, et al., Synthesis of palladium nanoparticles supported on mesoporous N-doped carbon and their catalytic ability for biofuel upgrade, J. Am. Chem. Soc. 134(2012) 16987-16990.
15. [15]
  [15] M. Li, X. Xu, Y. Gong, et al., Ultrafinely dispersed Pd nanoparticles on a CN@MgO hybrid as a bifunctional catalyst for upgrading bioderived compounds, Green Chem. 16(2014) 4371.
16. [16]
  [16] Y. Wang, J. Yao, H.R. Li, D.S. Su, M. Antonietti, Highly selective hydrogenation of phenol and derivatives over a Pd@carbon nitride catalyst in aqueous media, J. Am. Chem. Soc. 133(2011) 2362-2365.
17. [17]
  [17] M. Hu, J. Reboul, S. Furukawa, et al., Direct carbonization of Al-based porous coordination polymer for synthesis of nanoporous carbon, J. Am. Chem. Soc. 134(2012) 2864-2867.
18. [18]
  [18] L. Zhang, Z. Su, F. Jiang, et al., Highly graphitized nitrogen-doped porous carbon nanopolyhedra derived from ZIF-8 nanocrystals as efficient electrocatalysts for oxygen reduction reactions, Nanoscale 6(2014) 6590-6602.
19. [19]
  [19] X. Zhao, H. Zhao, T. Zhang, et al., One-step synthesis of nitrogen-doped microporous carbon materials as metal-free electrocatalysts for oxygen reduction reaction, J. Mater. Chem. A 2(2014) 11666.
20. [20]
  [20] W. Chaikittisilp, M. Hu, H.J. Wang, et al., Nanoporous carbons through direct carbonization of a zeolitic imidazolate framework for supercapacitor electrodes, Chem. Commun. 48(2012) 7259-7261.
21. [21]
  [21] X.L. Yan, X.J. Li, Z.F. Yan, S. Komarneni, Porous carbons prepared by direct carbonization of MOFs for supercapacitors, Appl. Surf. Sci. 308(2014) 306-310.
22. [22]
  [22] F. Afsahi, H.V. Thang, S. Mikhailenko, S. Kaliaguine, Electrocatalyst synthesized from metal organic frameworks, J. Power Sources 239(2013) 415-423.
23. [23]
  [23] W. Chaikittisilp, K. Ariga, Y. Yamauchi, A new family of carbon materials:synthesis of MOF-derived nanoporous carbons and their promising applications, J. Mater. Chem. A 1(2013) 14-19.
24. [24]
  [24] H.L. Jiang, B. Liu, Y.Q. Lan, et al., From metal-organic framework to nanoporous carbon:toward a very high surface area and hydrogen uptake, J. Am. Chem. Soc. 133(2011) 11854-11857.
25. [25]
  [25] J. Kim, N.D. McNamara, T.H. Her, J.C. Hicks, Carbothermal reduction of Ti-modified IRMOF-3:an adaptable synthetic method to support catalytic nanoparticles on carbon, ACS Appl. Mater. Interfaces 5(2013) 11479-11487.
26. [26]
  [26] G. Srinivas, V. Krungleviciute, Z.X. Guo, T. Yildirim, T. Yildirim, Exceptional CO₂ capture in a hierarchically porous carbon with simultaneous high surface area and pore volume, Energy Environ. 7(2014) 335-342.
27. [27]
  [27] T. Ahnfeldt, N. Guillou, D. Gunzelmann, et al.,[Al₄(OH)₂(OCH₃)₄(H₂Nbdc)₃]·xH₂O:a 12-connected porous metal-organic framework with an unprecedented aluminum-containing brick, Angew. Chem. Int. Ed. Engl. 48(2009) 5163-5166.
28. [28]
  [28] Y.Y. Lu, W.W. Zhan, Y. He, et al., MOF-templated synthesis of porous Co₃O₄ concave nanocubes with high specific surface area and their gas sensing properties, ACS Appl. Mater. Interfaces 6(2014) 4186-4195.
29. [29]
  [29] S.J. Yang, T. Kin, J.H. Im, et al., MOF-derived hierarchically porous carbon with exceptional porosity and hydrogen storage capacity, Chem. Mater. 24(2012) 464-470.
30. [30]
  [30] S.J. Yang, T. Kim, K. Lee, et al., Solvent evaporation mediated preparation of hierarchically porous metal organic framework-derived carbon with controllable and accessible large-scale porosity, Carbon 71(2014) 294-302.
31. [31]
  [31] H.B. Aiyappa, P. Pachfule, R. Banerjee, S. Kurungot, Porous carbons from nonporous MOFs:influence of ligand characteristics on intrinsic properties of end carbon, Cryst. Growth Des. 13(2013) 4195-4199.
32. [32]
  [32] N.Z. Shang, S.T. Gao, X. Zhou, et al. Palladium nanoparticles encapsulated inside the pores of a metal-organic framework as a highly active catalyst for carbon-carbon cross-coupling RSC Adv. 4(2014) 54487-54493.
33. [33]
  [33] L. Zhang, C. Feng, S.T. Gao, Z. Wang, C. Wang, Palladium nanoparticles supported on metal organic framework derived N-decorated nanoporous carbon as an efficient catalyst for the Suzuki coupling reaction, Catal. Commun. 61(2015) 21-25.
34. [34]
  [34] X. Liu, L. Zhou, Y. Zhao, et al., Hollow, spherical nitrogen-rich porous carbon shells obtained from a porous organic framework for the supercapacitor, ACS Appl. Mater. Interfaces 5(2013) 10280-10287.
35. [35]
  [35] S.Y. Lin, X. Yang, L.Y. Yang, R.X. Zhou, Three-way catalytic performance of Pd/Ce_0.67Zr_0.33O₂-Al₂O₃ catalysts:role of the different Pd precursors, Appl. Surf. Sci. 327(2015) 335-343.
36. [36]
  [36] A. Maksic, Z. Rakocevic, M. Smiljanic, M. Nenadovic, S. Strbac, Methanol oxidation on Pd/Pt(poly) in alkaline solution, J. Power Sources 273(2015) 724-734.
37. [37]
  [37] E. Negro, A.H.A.M. Videla, V. Baglio, et al., Fe-N supported on graphitic carbon nano-networks grown from cobalt as oxygen reduction catalysts for low-temperature fuel cells, Appl. Catal. B:Environ. 166-167(2015) 75-83.
38. [38]
  [38] S.Z. Wu, Y.X. Yu, W.D. Zhang, Processing graphitic carbon nitride for improved photocatalytic activity, Mat. Sci. Semicon. Proc. 24(2014) 15-20.
39. [39]
  [39] B. Liu, T. Akita, Q. Xu, Metal-organic framework as a template for porous carbon synthesis, J. Am. Chem. Soc. 130(2008) 5390-5391.
40. [40]
  [40] M.R. Feyyaz Durap, M. Aydemir, S. Ö zkar, Room temperature aerobic Suzuki cross-coupling reactions in DMF/water mixture using zeolite confined palladium(0) nanoclusters as efficient and recyclable catalyst, Appl. Catal. A:Gen. 382(2010) 339-344.
1. [1]
  Tengjia Ni , Xianbiao Hou , Huanlei Wang , Lei Chu , Shuixing Dai , Minghua Huang . Controllable defect engineering based on cobalt metal-organic framework for boosting oxygen evolution reaction. Chinese Journal of Structural Chemistry, 2024, 43(1): 100210-100210. doi: 10.1016/j.cjsc.2023.100210
2. [2]
  Jiayu Huang , Kuan Chang , Qi Liu , Yameng Xie , Zhijia Song , Zhiping Zheng , Qin Kuang . Fe-N-C nanostick derived from 1D Fe-ZIFs for Electrocatalytic oxygen reduction. Chinese Journal of Structural Chemistry, 2023, 42(10): 100097-100097. doi: 10.1016/j.cjsc.2023.100097
3. [3]
  Muhammad Riaz , Rakesh Kumar Gupta , Di Sun , Mohammad Azam , Ping Cui . Selective adsorption of organic dyes and iodine by a two-dimensional cobalt(II) metal-organic framework. Chinese Journal of Structural Chemistry, 2024, 43(12): 100427-100427. doi: 10.1016/j.cjsc.2024.100427
4. [4]
  Xi Feng , Ding-Yi Hu , Zi-Jun Liang , Mu-Yang Zhou , Zhi-Shuo Wang , Wen-Yu Su , Rui-Biao Lin , Dong-Dong Zhou , Jie-Peng Zhang . A metal azolate framework with small aperture for highly efficient ternary benzene/cyclohexene/cyclohexane separation. Chinese Journal of Structural Chemistry, 2025, 44(3): 100540-100540. doi: 10.1016/j.cjsc.2025.100540
5. [5]
  Ze Liu , Xiaochen Zhang , Jinlong Luo , Yingjian Yu . Application of metal-organic frameworks to the anode interface in metal batteries. Chinese Chemical Letters, 2024, 35(11): 109500-. doi: 10.1016/j.cclet.2024.109500
6. [6]
  Longlong Geng , Huiling Liu , Wenfeng Zhou , Yong-Zheng Zhang , Hongliang Huang , Da-Shuai Zhang , Hui Hu , Chao Lv , Xiuling Zhang , Suijun Liu . Construction of metal-organic frameworks with unsaturated Cu sites for efficient and fast reduction of nitroaromatics: A combined experimental and theoretical study. Chinese Chemical Letters, 2024, 35(8): 109120-. doi: 10.1016/j.cclet.2023.109120
7. [7]
  Rui Wang , He Qi , Haijiao Zheng , Qiong Jia . Light/pH dual-responsive magnetic metal-organic frameworks composites for phosphorylated peptide enrichment. Chinese Chemical Letters, 2024, 35(7): 109215-. doi: 10.1016/j.cclet.2023.109215
8. [8]
  Fereshte Hassanzadeh-Afruzi , Mina Azizi , Iman Zare , Ehsan Nazarzadeh Zare , Anwarul Hasan , Siavash Iravani , Pooyan Makvandi , Yi Xu . Advanced metal-organic frameworks-polymer platforms for accelerated dermal wound healing. Chinese Chemical Letters, 2024, 35(11): 109564-. doi: 10.1016/j.cclet.2024.109564
9. [9]
  Xiao-Hong Yi , Chong-Chen Wang . Metal-organic frameworks on 3D interconnected macroporous sponge foams for large-scale water decontamination: A mini review. Chinese Chemical Letters, 2024, 35(5): 109094-. doi: 10.1016/j.cclet.2023.109094
10. [10]
  Fahui Xiang , Lu Li , Zhen Yuan , Wuji Wei , Xiaoqing Zheng , Shimin Chen , Yisi Yang , Liangji Chen , Zizhu Yao , Jianwei Fu , Zhangjing Zhang , Shengchang Xiang . Enhanced C₂H₂/CO₂ separation in tetranuclear Cu(Ⅱ) cluster-based metal-organic frameworks by adjusting divider length of pore space partition. Chinese Chemical Letters, 2025, 36(3): 109672-. doi: 10.1016/j.cclet.2024.109672
11. [11]
  Yuan Zhang , Shenghao Gong , A.R. Mahammed Shaheer , Rong Cao , Tianfu Liu . Plasmon-enhanced photocatalytic oxidative coupling of amines in the air using a delicate Ag nanowire@NH₂-UiO-66 core-shell nanostructures. Chinese Chemical Letters, 2024, 35(4): 108587-. doi: 10.1016/j.cclet.2023.108587
12. [12]
  Yue Sun , Yingnan Zhu , Jiahang Si , Ruikang Zhang , Yalan Ji , Jinjie Fan , Yuze Dong . Glucose-activated nanozyme hydrogels for microenvironment modulation via cascade reaction in diabetic wound. Chinese Chemical Letters, 2025, 36(4): 110012-. doi: 10.1016/j.cclet.2024.110012
13. [13]
  Wenbiao Zhang , Bolong Yang , Zhonghua Xiang . Atomically dispersed Cu-based metal-organic framework directly for alkaline polymer electrolyte fuel cells. Chinese Chemical Letters, 2025, 36(2): 109630-. doi: 10.1016/j.cclet.2024.109630
14. [14]
  Xudong Zhao , Yuxuan Wang , Xinxin Gao , Xinli Gao , Meihua Wang , Hongliang Huang , Baosheng Liu . Anchoring thiol-rich traps in 1D channel wall of metal-organic framework for efficient removal of mercury ions. Chinese Chemical Letters, 2025, 36(2): 109901-. doi: 10.1016/j.cclet.2024.109901
15. [15]
  Sixiao Liu , Tianyi Wang , Lei Zhang , Chengyin Wang , Huan Pang . Cerium-based metal-organic framework-modified natural mineral vermiculite for photocatalytic nitrogen fixation under visible-light irradiation. Chinese Chemical Letters, 2025, 36(3): 110058-. doi: 10.1016/j.cclet.2024.110058
16. [16]
  Jian Peng , Yue Jiang , Shuangyu Wu , Yanran Cheng , Jingyu Liang , Yixin Wang , Zhuo Li , Sijie Lin . A nonradical oxidation process initiated by Ti-peroxo complex showed high specificity toward the degradation of tetracycline antibiotics. Chinese Chemical Letters, 2024, 35(5): 108903-. doi: 10.1016/j.cclet.2023.108903
17. [17]
  Zhi Wang , Lingpeng Yan , Yelin Hao , Jingxia Zheng , Yongzhen Yang , Xuguang Liu . Highly efficient and photothermally stable CDs@ZIF-8 for laser illumination. Chinese Chemical Letters, 2024, 35(10): 109430-. doi: 10.1016/j.cclet.2023.109430
18. [18]
  Hao Wang , Meng-Qi Pan , Ya-Fei Wang , Chao Chen , Jian Xu , Yuan-Yuan Gao , Chuan-Song Qi , Wei Li , Xian-He Bu . Post-synthetic modifications of MOFs by different bolt ligands for controllable release of cargoes. Chinese Chemical Letters, 2024, 35(10): 109581-. doi: 10.1016/j.cclet.2024.109581
19. [19]
  Yan-Kai Zhang , Yong-Zheng Zhang , Chun-Xiao Jia , Fang Wang , Xiuling Zhang , Yuhang Wu , Zhongmin Liu , Hui Hu , Da-Shuai Zhang , Longlong Geng , Jing Xu , Hongliang Huang . A stable Zn-MOF with anthracene-based linker for Cr(VI) photocatalytic reduction under sunlight irradiation. Chinese Chemical Letters, 2024, 35(12): 109756-. doi: 10.1016/j.cclet.2024.109756
20. [20]
  Yi Zhou , Yanzhen Liu , Yani Yan , Zonglin Yi , Yongfeng Li , Cheng-Meng Chen . Enhanced oxygen reduction reaction on La-Fe bimetal in porous N-doped carbon dodecahedra with CNTs wrapping. Chinese Chemical Letters, 2025, 36(1): 109569-. doi: 10.1016/j.cclet.2024.109569

Get Citation

PDF

XML

Metrics

PDF Downloads(0)
Abstract views(693)
HTML views(6)

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