Citation: Zhan Kan, Lu Ping, Dong Jian, Hou Xu. Polymer hydrogel confined palladium nanoparticles as recyclable catalysts for Suzuki and Heck cross-coupling reactions[J]. Chinese Chemical Letters, ;2020, 31(6): 1630-1634. doi: 10.1016/j.cclet.2019.09.006 shu

Polymer hydrogel confined palladium nanoparticles as recyclable catalysts for Suzuki and Heck cross-coupling reactions

Zhan Kan ^a,b,*, ,
Lu Ping ^a ,
Dong Jian ^a,*, ,
Hou Xu ^b

a.
School of Chemistry and Chemical Engineering, Shaoxing University, Shaoxing 312000, China
b.
School of Chemistry and Chemical Engineering, Xiamen University, Xiamen 361005, China

kanzhan@xmu.edu.cn

jiandong@usx.edu.cn

Received Date: 16 July 2019
Revised Date: 23 August 2019
Accepted Date: 5 September 2019
Available Online: 5 September 2019

Figures(3)

Reusable palladium nanoparticles highly dispersed in porous and hydrophilic interpenetrating polymer networks (IPN), i.e., Pd@IPN hybrid gels, are employed for catalysis of Suzuki and Heck coupling reactions. Good yields are obtained with high turnover frequencies when the reactions are run with very low Pdloadings. The use of IPN gives better recyclability than that of crosslinked polyvinyl alcohol alone. The polymer networks allow the reactants to have easy access to the Pd metals. The catalysts combine high activity with the reusability offered by the heterogeneous system, without the need for strong coordination or chelating ligands.
- Nanoparticle,
- Catalysis,
- Hydrogels,
- Palladium,
- Water
1. [1]
  A.J. Reay, I.J. Fairlamb, Chem. Commun. 51(2015) 16289-16307. doi: 10.1039/C5CC06980G
2. [2]
  A. Biffis, P. Centomo, A. Del Zotto, M. Zecca, Chem. Rev. 118(2018) 2249-2295. doi: 10.1021/acs.chemrev.7b00443
3. [3]
  A. Balanta, C. Godard, C. Claver, Chem. Soc. Rev. 40(2011) 4973-4985. doi: 10.1039/c1cs15195a
4. [4]
  L. Liu, A. Corma, Chem. Rev. 118(2018) 4981-5079. doi: 10.1021/acs.chemrev.7b00776
5. [5]
  A. Molnar, Chem. Rev. 111(2011) 2251-2320. doi: 10.1021/cr100355b
6. [6]
  S.J. Guo, J. Bai, H.O. Liang, C.P. Li, Chin. Chem. Lett. 27(2016) 459-463. doi: 10.1016/j.cclet.2015.12.029
7. [7]
  L. Zhang, W.H. Dong, N.Z. Shang, et al., Chin. Chem. Lett. 27(2016) 149-154. doi: 10.1016/j.cclet.2015.08.007
8. [8]
  Y. Li, X.M. Hong, D.M. Collard, M.A. El-Sayed, Org. Lett. 2(2000) 2385-2388. doi: 10.1021/ol0061687
9. [9]
  R. Narayanan, M.A. El-Sayed, J. Am. Chem. Soc. 125(2003) 8340-8347. doi: 10.1021/ja035044x
10. [10]
  Y. Li, E. Boone, M.A. El-Sayed, Langmuir 18(2002) 4921-4925. doi: 10.1021/la011469q
11. [11]
  R. Narayanan, M.A. El-Sayed, J. Phys. Chem. B 108(2004) 8572-8580. doi: 10.1021/jp037169u
12. [12]
  Y. Li, M.A. El-Sayed, J. Phys. Chem. B 105(2001) 8938-8943. doi: 10.1021/jp010904m
13. [13]
  F. Durap, A. Baysal, D. Elma, M. Aydemir, Ö. Ok, Z. Baysal, Synth. React. Inorg. Met. 46(2016) 1402-1409. doi: 10.1080/15533174.2015.1136954
14. [14]
  D. Kale, G. Rashinkar, A. Kumbhar, R. Salunkhe, React. Funct. Polym.116(2017) 9-16.
15. [15]
  M. Pittelkow, K. Moth-Poulsen, U. Boas, J.B. Christensen, Langmuir 19(2003) 7682-7684. doi: 10.1021/la0348822
16. [16]
  M. Pérez-Lorenzo, J. Phys. Chem. Lett. 3(2012) 167-174. doi: 10.1021/jz2013984
17. [17]
  L. Strimbu, J. Liu, A.E. Kaifer, Langmuir 19(2003) 483-485. doi: 10.1021/la026550n
18. [18]
  A. Biffis, E. Sperotto, Langmuir 19(2003) 9548-9550. doi: 10.1021/la0350709
19. [19]
  D.Kundu, A.K.Patra, J.Sakamoto, H.Uyama, React.Funct. Polym.79(2014)8-13. doi: 10.1016/j.reactfunctpolym.2014.03.002
20. [20]
  J.K. Cho, R. Najman, T.W. Dean, et al., J. Am. Chem. Soc. 128(2006) 6276-6277. doi: 10.1021/ja057480k
21. [21]
  S. Ogasawara, S. Kato, J. Am. Chem. Soc. 132(2010) 4608-4613. doi: 10.1021/ja9062053
22. [22]
  P.M. Uberman, L.A. Pérez, G.I. Lacconi, S.E. Martín, J. Mol. Catal. A:Chem. 363(2012) 245-253.
23. [23]
  M.S.A.S. Shah, D. Guin, S.V.Manorama, Mater. Chem. Phys.124(2010) 664-669. doi: 10.1016/j.matchemphys.2010.07.031
24. [24]
  P. Centomo, M. Zecca, M. Kralik, et al., J. Mol. Catal. A:Chem. 300(2009) 48-58. doi: 10.1016/j.molcata.2008.10.039
25. [25]
  Y.Zhang, J.Yang, X.Zhang, F.Bian, W.Yu, React.Funct.Polym.72(2012)233-241. doi: 10.1016/j.reactfunctpolym.2012.02.010
26. [26]
  Y. Wang, C. Lu, G. Yang, Z. Chen, J. Nie, React. Funct. Polym. 110(2017) 38-46. doi: 10.1016/j.reactfunctpolym.2016.12.003
27. [27]
  K. Zhan, H. You, W. Liu, et al., React. Funct. Polym. 71(2011) 756-765. doi: 10.1016/j.reactfunctpolym.2011.04.007
28. [28]
  N.T. Phan, M. Van Der Sluys, C.W. Jones, Adv. Synth. Catal. 348(2006) 609-679. doi: 10.1002/adsc.200505473
29. [29]
  A.K. Diallo, C. Ornelas, L. Salmon, J. Ruiz Aranzaes, D. Astruc, Angew. Chem. Int. Ed. 46(2007) 8644-8648. doi: 10.1002/anie.200703067
30. [30]
  L. Joucla, G. Cusati, C. Pinel, L. Djakovitch, Appl. Catal. A:Gen. 360(2009) 145-153. doi: 10.1016/j.apcata.2009.03.016
31. [31]
  J.-S. Chen, A.N. Vasiliev, A.P. Panarello, J.G. Khinast, Appl. Catal. A:Gen. 325(2007) 76-86. doi: 10.1016/j.apcata.2007.03.010
32. [32]
  S.P. Andrews, A.F. Stepan, H. Tanaka, S.V. Ley, M.D. Smith, Adv. Synth. Catal. 347(2005) 647-654. doi: 10.1002/adsc.200404331
33. [33]
  J.M. Richardson, C.W. Jones, J. Catal. 251(2007) 80-93. doi: 10.1016/j.jcat.2007.07.005
34. [34]
  Y.-H. Chen, H.-H. Hung, M.H. Huang, J. Am. Chem. Soc. 131(2009) 9114-9121. doi: 10.1021/ja903305d
35. [35]
  Y. Ma, X. Ma, Q. Wang, J. Zhou, Catal. Sci. Technol. 2(2012) 1879-1885. doi: 10.1039/c2cy00001f
36. [36]
  L.A. Adrio, B.N. Nguyen, G. Guilera, A.G. Livingston, K.K.M. Hii, Catal. Sci. Technol. 2(2012) 316-323. doi: 10.1039/C1CY00241D
37. [37]
  R.U.Islam, M.J.Witcomb, M.S.Scurrell, etal., Catal.Sci.Technol.1(2011)308-315. doi: 10.1039/c0cy00071j
38. [38]
  J.R. Ruiz, C. Jiménez-Sanchidrián, M. Mora, Tetrahedron 62(2006) 2922-2926.
39. [39]
  M. Mora, C. Jiménez-Sanchidrián, J.R. Ruiz, J. Colloid Interface Sci. 302(2006) 568-575. doi: 10.1016/j.jcis.2006.06.058
40. [40]
  R. Narayanan, M.A. El-Sayed, J. Catal. 234(2005) 348-355. doi: 10.1016/j.jcat.2005.06.024
41. [41]
  S.S.Soomro, F.L.Ansari, K.Chatziapostolou, K.Köhler, J.Catal.273(2010)138-146. doi: 10.1016/j.jcat.2010.05.007
42. [42]
  A. Ohtaka, Y. Tamaki, Y. Igawa, et al., Tetrahedron 66(2010) 5642-5646. doi: 10.1016/j.tet.2010.05.076
1. [1]
  Fangling Cui , Zongjie Hu , Jiayu Huang , Xiaoju Li , Ruihu Wang . MXene-based materials for separator modification of lithium-sulfur batteries. Chinese Journal of Structural Chemistry, 2024, 43(7): 100337-100337. doi: 10.1016/j.cjsc.2024.100337
2. [2]
  Hailong He , Wenbing Wang , Wenmin Pang , Chen Zou , Dan Peng . Double stimulus-responsive palladium catalysts for ethylene polymerization and copolymerization. Chinese Chemical Letters, 2024, 35(7): 109534-. doi: 10.1016/j.cclet.2024.109534
3. [3]
  Xiaohui Fu , Yanping Zhang , Juan Liao , Zhen-Hua Wang , Yong You , Jian-Qiang Zhao , Mingqiang Zhou , Wei-Cheng Yuan . Palladium-catalyzed enantioselective decarboxylation of vinyl cyclic carbamates: Generation of amide-based aza-1,3-dipoles and application to asymmetric 1,3-dipolar cycloaddition. Chinese Chemical Letters, 2024, 35(12): 109688-. doi: 10.1016/j.cclet.2024.109688
4. [4]
  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
5. [5]
  Shuai Li , Liuting Zhang , Fuying Wu , Yiqun Jiang , Xuebin Yu . Efficient catalysis of FeNiCu-based multi-site alloys on magnesium-hydride for solid-state hydrogen storage. Chinese Chemical Letters, 2025, 36(1): 109566-. doi: 10.1016/j.cclet.2024.109566
6. [6]
  Jiajia Wang , XinXin Ge , Yajing Xiang , Xiaoliang Qi , Ying Li , Hangbin Xu , Erya Cai , Chaofan Zhang , Yulong Lan , Xiaojing Chen , Yizuo Shi , Zhangping Li , Jianliang Shen . An ionic liquid functionalized sericin hydrogel for drug-resistant bacteria-infected diabetic wound healing. Chinese Chemical Letters, 2025, 36(2): 109819-. doi: 10.1016/j.cclet.2024.109819
7. [7]
  Chengde Wang , Liping Huang , Shanshan Wang , Lihao Wu , Yi Wang , Jun Dong . A distinction of gliomas at cellular and tissue level by surface-enhanced Raman scattering spectroscopy. Chinese Chemical Letters, 2024, 35(5): 109383-. doi: 10.1016/j.cclet.2023.109383
8. [8]
  Shuang Liang , Jianjun Yao , Dan Liu , Mengli Zhou , Yong Cui , Zhaohui Wang . Tumor-responsive covalent organic polymeric nanoparticles enhancing STING activation for cancer immunotherapy. Chinese Chemical Letters, 2025, 36(3): 109856-. doi: 10.1016/j.cclet.2024.109856
9. [9]
  Haodong Wang , Xiaoxu Lai , Chi Chen , Pei Shi , Houzhao Wan , Hao Wang , Xingguang Chen , Dan Sun . Novel 2D bifunctional layered rare-earth hydroxides@GO catalyst as a functional interlayer for improved liquid-solid conversion of polysulfides in lithium-sulfur batteries. Chinese Chemical Letters, 2024, 35(5): 108473-. doi: 10.1016/j.cclet.2023.108473
10. [10]
  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
11. [11]
  Manoj Kumar Sarangi , L․D Patel , Goutam Rath , Sitansu Sekhar Nanda , Dong Kee Yi . Metal organic framework modulated nanozymes tailored with their biomedical approaches. Chinese Chemical Letters, 2024, 35(11): 109381-. doi: 10.1016/j.cclet.2023.109381
12. [12]
  Mengxiang Zhu , Tao Ding , Yunzhang Li , Yuanjie Peng , Ruiping Liu , Quan Zou , Leilei Yang , Shenglei Sun , Pin Zhou , Guosheng Shi , Dongting Yue . Graphene controlled solid-state growth of oxygen vacancies riched V₂O₅ catalyst to highly activate Fenton-like reaction. Chinese Chemical Letters, 2024, 35(12): 109833-. doi: 10.1016/j.cclet.2024.109833
13. [13]
  Fengxing Liang , Yongzheng Zhu , Nannan Wang , Meiping Zhu , Huibing He , Yanqiu Zhu , Peikang Shen , Jinliang Zhu . Recent advances in copper-based materials for robust lithium polysulfides adsorption and catalytic conversion. Chinese Chemical Letters, 2024, 35(11): 109461-. doi: 10.1016/j.cclet.2023.109461
14. [14]
  Shule Liu . Application of SPC/E Water Model in Molecular Dynamics Teaching Experiments. University Chemistry, 2024, 39(4): 338-342. doi: 10.3866/PKU.DXHX202310029
15. [15]
  Yanhui Zhong , Ran Wang , Zian Lin . Analysis of Halogenated Quinone Compounds in Environmental Water by Dispersive Solid-Phase Extraction with Liquid Chromatography-Triple Quadrupole Mass Spectrometry. University Chemistry, 2024, 39(11): 296-303. doi: 10.12461/PKU.DXHX202402017
16. [16]
  Lijuan Liu , Xionglei Wang . Preparation of Hydrogels from Waste Thermosetting Unsaturated Polyester Resin by Controllable Catalytic Degradation: A Comprehensive Chemical Experiment. University Chemistry, 2024, 39(11): 313-318. doi: 10.12461/PKU.DXHX202403060
17. [17]
  Zijian Jiang , Yuang Liu , Yijian Zong , Yong Fan , Wanchun Zhu , Yupeng Guo . Preparation of Nano Zinc Oxide by Microemulsion Method and Study on Its Photocatalytic Activity. University Chemistry, 2024, 39(5): 266-273. doi: 10.3866/PKU.DXHX202311101
18. [18]
  Ran Yu , Chen Hu , Ruili Guo , Ruonan Liu , Lixing Xia , Cenyu Yang , Jianglan Shui . 杂多酸H₃PW₁₂O₄₀高效催化MgH₂储氢. Acta Physico-Chimica Sinica, 2025, 41(1): 2308032-. doi: 10.3866/PKU.WHXB202308032
19. [19]
  Binhan Zhao , Zheng Li , Lan Zheng , Zhichao Ye , Yuyang Yuan , Shanshan Zhang , Bo Liang , Tianyu Li . Recent progress in the biomedical application of PEDOT:PSS hydrogels. Chinese Chemical Letters, 2024, 35(10): 109810-. doi: 10.1016/j.cclet.2024.109810
20. [20]
  Shiyan Cheng , Yonghong Ruan , Lei Gong , Yumei Lin . Research Advances in Friedel-Crafts Alkylation Reaction. University Chemistry, 2024, 39(10): 408-415. doi: 10.12461/PKU.DXHX202403024

Get Citation

PDF

XML

Metrics

PDF Downloads(14)
Abstract views(1558)
HTML views(86)

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