Citation: Xiao-Peng HU, Zhi-Feng WANG, Wei DENG, Jin TONG, Shu-Yan YU. Molecular Structures and Catalytical Performance in Suzuki-coupling Reaction of Novel Dipalladium Clip-shaped Complexes with Bifunctional Pyrazolate Ligands[J]. Chinese Journal of Structural Chemistry, ;2021, 40(7): 843-850. doi: 10.14102/j.cnki.0254-5861.2011-3174 shu

Molecular Structures and Catalytical Performance in Suzuki-coupling Reaction of Novel Dipalladium Clip-shaped Complexes with Bifunctional Pyrazolate Ligands

Laboratory for Self-assembly Chemistry, Center of Excellence for Environmental Safety and Biological Effects, Beijing Key Laboratory for Green Catalysis and Separation, Department of Environment and Life, Beijing University of Technology, Beijing 100124, China

Corresponding author: Shu-Yan YU, selfassembly@bjut.edu.cn
Received Date: 11 March 2011
Accepted Date: 27 May 2021

Fund Project: the Beijing Natural Science Foundation of China 2212002National Natural Science Foundation of China 21906002National Natural Science Foundation of China 21471011the Beijing Municipal Science and Technology Project KM202010005010the Beijing Municipal High Level Innovative Team Building Program IDHT20180504the Beijing Outstanding Young Scientist Program BJJWZYJH01201910005017

Figures(5)

A series of clip-shaped cationic molecular corners C1~C4 (C1 = [(bpy)₂Pd₂(L¹)₂]²⁺, C2 = [(dmbpy)₂Pd₂(L¹)₂]²⁺, C3 = (bpy)₂Pd₂(L²)₂]²⁺, C4 = (dmbpy)₂Pd₂(L²)₂]²⁺, bpy = 2, 2-bipyridine, dmbpy = 4, 4΄-dimethyl-2, 2-bipyridine) were synthesized through dipalladium complexes [(bpy)₂Pd₂(NO₃)₂](NO₃)₂, [(dmbpy)₂Pd₂(NO₃)₂](NO₃)₂ and bifunctional pyrazole ligands 4-(3, 4-dimethoxyphenyl)-3, 5-dimethyl-1H-pyrazol (HL¹) and 4, 4΄-(5-(1H-pyrazol-4-yl)-1, 3-phenylene)dipyridine (HL²). Complexes C1~C4 were characterized by ¹H and ¹³C NMR, electrospray ionization mass spectrometry (ESI-MS), elemental analysis, and IR spectroscopy. The X-ray diffraction analysis of C1∙2NO₃⁻ revealed a Pd₂ dimetallic clip-shaped structure which was synthesized by two bifunctional ligands doubly bridged by the [(bpy)Pd]₂ dimetal units. Additionally, all of the complexes with NO₃⁻ as counter anions exhibited high-efficiency catalytical performance in the Suzuki-coupling reaction attributed to the tunable impact and weak dinuclear Pd(Ⅱ)…Pd(Ⅱ) intramolecular bonding interaction.
- dipalladium supra molecules,
- bifunctional pyrazolate ligands,
- catalysis,
- Suzuki-coupling reaction
1. [1]
  Sauvage, J. P. Transition Metals in Supramolecular Chemistry, Perspectives in Supramolecular Chemistry. Vol. 5, Wiley, New York 1999.
2. [2]
  Fujita, M. Molecular Self-assembly Organic Versus Inorganic Approach (Structure and Bonding). Vol. 96, Springer, New York 2000.
3. [3]
  Chakrabarty, R.; Mukherjee, P. S.; Stang, P. J. Supramolecular coordination: self-assembly of finite two- and three-dimensional ensembles. Chem. Rev. 2011, 111, 6810–6918. doi: 10.1021/cr200077m
4. [4]
  Wang, W.; Wang, Y. X.; Yang, H. B. Supramolecular transformations within discrete coordination-driven supramolecular architectures. Chem. Soc. Rev. 2016, 45, 2656–2693. doi: 10.1039/C5CS00301F
5. [5]
  Care, J. B. Introduction to Ligand Field Theory. New York: McGraw Hill 1962.
6. [6]
  Brown, C. J.; Toste, F. D.; Bergman, R. G.; Raymond, K. N. Supramolecular catalysis in metal-ligand cluster hosts. Chem. Rev. 2015, 115, 3012–3035. doi: 10.1021/cr4001226
7. [7]
  Xu, H.; Chen, R. F.; Sun, Q.; Lai, W. Y.; Su, Q. Q.; Huang, W.; Liu, X. G. Recent progress in metal-organic complexes for optoelectronic applications. Chem. Soc. Rev. 2014, 43, 3259–3302. doi: 10.1039/C3CS60449G
8. [8]
  Tiwari, V. K.; Mishra, B. B.; Mishra, K. B.; Mishra, N.; Singh, A.; Chen, X. Cu-catalyzed click reaction in carbohydrate chemistry. Chem. Rev. 2016, 116, 3086–3240. doi: 10.1021/acs.chemrev.5b00408
9. [9]
  Yu, S. Y.; Li, S. H.; Huang, H. P.; Zhang, Z. X.; Jiao, Q.; Shen, H.; Hu, X. X.; Huang, H. Molecular self-assembly with modularization and directionality: vectormanipulation at metal centers. Curr. Org. Chem. 2005, 9, 555–563. doi: 10.2174/1385272053544416
10. [10]
  Ismayilov, R. H.; Wang, W. Z.; Lee, G. H.; Yeh, C. Y.; Hua, S. A.; Song, Y.; Rohmer, M. M.; Bénard, M.; Peng, S. M. Two linear undecanickel mixed-valence complexes: increasing the size and the scope of the electronic properties of nickel metal strings. Angew. Chem. Int. Ed. 2011, 50, 2045–2048. doi: 10.1002/anie.201006695
11. [11]
  Mitsumi, M.; Ueda, H.; Furukawa, K.; Ozawa, Y.; Toriumi, K.; Kurmoo, M. Constructing highly conducting metal-metal bonded solids by electrocrystallization of [Pt₂^Ⅱ(RCS₂)₄] (RCS₂⁻ = dithiocarboxylato, R = methyl or ethyl). J. Am. Chem. Soc. 2008, 130, 14102–14104. doi: 10.1021/ja805794a
12. [12]
  Qin, J. H.; Huang, Y. D.; Shi, M. Y.; Wang, H. R.; Han, M. L.; Yang, X. G.; Li, F. F.; Ma, L. F. Aqueous-phase detection of antibiotics and nitroaromatic explosives by an alkali-resistant Zn-MOF directed by anionic liquid. RSC Adv. 2020, 10, 1439–1446. doi: 10.1039/C9RA08733H
13. [13]
  Yam, V. W. W.; Au, V. K. M.; Leung, S. Y. L. Light-emitting self-assembled materials based on d⁸ and d¹⁰ transition metal complexes. Chem. Rev. 2015, 115, 7589–7728. doi: 10.1021/acs.chemrev.5b00074
14. [14]
  Marques, A. J.; Palanimurugan, R.; Matias, A. C.; Ramos, P. C.; Dohme, R. J. Catalytic mechanism and assembly of the proteasom. Chem. Rev. 2009, 109, 1509–1536. doi: 10.1021/cr8004857
15. [15]
  Park, J.; Hong, S. Cooperative bimetallic catalysis in asymmetric transformations. Chem. Soc. Rev. 2012, 41, 6931–6943. doi: 10.1039/c2cs35129c
16. [16]
  Qin, J. H.; Huang, Y. D.; Zhao, Y.; Yang, X. G.; Li, F. F.; Wang, C.; Ma, L. F. Highly dense packing of chromophoric linkers achievable in a pyrene-based metal-organic framework for photoelectric response. Inorg. Chem. 2019, 58, 15013–15016. doi: 10.1021/acs.inorgchem.9b02203
17. [17]
  Friis, S. D.; Pirnot, M. T.; Dupuis, L. N.; Buchwald, S. L. A dual palladium and copper hydride catalyzed approach for alkyl-alkyl cross-coupling of aryl halides and olefins. Angew. Chem. Int. Ed. 2017, 56, 7242–7724. doi: 10.1002/anie.201703400
18. [18]
  Zhang, J. J.; Hu, S. M.; Xiang, S. C.; Sheng, T.; Wu, X. T.; Li, Y. M. Syntheses, structures, and properties of high-nuclear 3d-4f clusters with amino acid as ligand: {Gd₆Cu₂₄}, {Tb₆Cu₂₆}, and {(Ln₆Cu₂₄)₂Cu} (Ln = Sm, Gd). Inorg. Chem. 2006, 45, 7173–7181. doi: 10.1021/ic060610l
19. [19]
  Yu, S. Y.; Lu, H. L. From metal-metal bonding to supra-metal-metal bonding directed self-assembly: supramolecular architectures of group 10 and 11 metals with ligands from mono- to poly-pyrazoles. Isr. J. Chem. 2019, 59, 166–183. doi: 10.1002/ijch.201800097
20. [20]
  Halcrow, M. A. Pyrazoles and pyrazolides-flexible synthons in self-assembly. Dalton Trans. 2009, 2059–2073.
21. [21]
  Chen, H.; Yu, Z. C.; Deng, W.; Jiang, X. F.; Yu, S. Y. Pyrazolate-based dipalladium (Ⅱ, Ⅱ) complexes: synthesis, characterization and catalytical performance in Suzuki-coupling reaction. Chin. J. Inorg. Chem. 2017, 33, 939–946.
22. [22]
  Qin, L.; Yao, L. Y.; Yu, S. Y. Self-assembly of [M₈L₄] and [M₄L₂] fluorescent metallo macrocycles with carbazole-based dipyrazole ligands. Inorg. Chem. 2012, 51, 2443–2453. doi: 10.1021/ic202407b
23. [23]
  Hu, Z. Y.; Deng, W.; Lu, H. L.; Huang, H. P.; Yu, S. Y. Mononuclear assemblies with metal-metal interaction: syntheses and catalytical performance in Suzuki-coupling reaction. Chin. J. Inorg. Chem. 2018, 34, 387–396.
24. [24]
  Brown, C. J.; Toste, F. D.; Bergman, R. G.; Raymond, K. N. Supramolecular catalysis in metal-ligand cluster hosts. Chem. Rev. 2015, 115, 3012–3035. doi: 10.1021/cr4001226
25. [25]
  Sun, W. Q.; Tong, J.; Lu, H. L.; Ma, T. T.; Ma, H. W.; Yu, S. Y. Programmable self-assembly of heterometallic palladium(Ⅱ)-copper(Ⅱ) 1D grid-chain using dinuclear palladium(Ⅱ) corners with pyrazole-carboxylic acid ligands. Chem. Asian J. 2018, 13, 1108–1113. doi: 10.1002/asia.201701766
26. [26]
  Hu, Z. Y.; Deng, W.; Lu, H. L.; Huang, H. P.; Yu, S. Y. Mononuclear assemblies with metal-metal interaction: syntheses and catalytical performance in suzuki-coupling reaction. Chin. J. Inorg. Chem. 2015, 31, 1278–1286.
27. [27]
  Sheldrick, G. M. SHELXS-97, Program for the Solution of Crystal Structure. University of Göttingen, Germany 1997.
28. [28]
  Sheldrick, G. M. SHELXL-97, Program for the Refinement of Crystal Structure. University of Göttingen, Germany 1997.
29. [29]
  Reek, J. N. H.; Arevalo, S.; Heerbeek, R. V.; Kamer, P. C. J.; Leeuwen, P. V. Advances in Catalysis, Vol 49, Academic Press, Amsterdam 2006, 71–151.
30. [30]
  Brown, H. C. Organic Syntheses via Boranes. Wiley, New York 2001.
1. [1]
  Conghui Wang , Lei Xu , Zhenhua Jia , Teck-Peng Loh . Recent applications of macrocycles in supramolecular catalysis. Chinese Chemical Letters, 2024, 35(4): 109075-. doi: 10.1016/j.cclet.2023.109075
2. [2]
  Wei Chen , Pieter Cnudde . A minireview to ketene chemistry in zeolite catalysis. Chinese Journal of Structural Chemistry, 2024, 43(11): 100412-100412. doi: 10.1016/j.cjsc.2024.100412
3. [3]
  Yu Mao , Yilin Liu , Xiaochen Wang , Shengyang Ni , Yi Pan , Yi Wang . Acylfluorination of enynes via phosphine and silver catalysis. Chinese Chemical Letters, 2024, 35(8): 109443-. doi: 10.1016/j.cclet.2023.109443
4. [4]
  Xianxu Chu , Lu Wang , Junru Li , Hui Xu . Surface chemical microenvironment engineering of catalysts by organic molecules for boosting electrocatalytic reaction. Chinese Chemical Letters, 2024, 35(8): 109105-. doi: 10.1016/j.cclet.2023.109105
5. [5]
  Ning LI , Siyu DU , Xueyi WANG , Hui YANG , Tao ZHOU , Zhimin GUAN , Peng FEI , Hongfang MA , Shang JIANG . Preparation and efficient catalysis for olefins epoxidation of a polyoxovanadate-based hybrid. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 799-808. doi: 10.11862/CJIC.20230372
6. [6]
  Uttam Pandurang Patil . Porous carbon catalysis in sustainable synthesis of functional heterocycles: An overview. Chinese Chemical Letters, 2024, 35(8): 109472-. doi: 10.1016/j.cclet.2023.109472
7. [7]
  Liliang Chu , Xiaoyan Zhang , Jianing Li , Xuelei Deng , Miao Wu , Ya Cheng , Weiping Zhu , Xuhong Qian , Yunpeng Bai . Continuous-flow synthesis of polysubstituted γ-butyrolactones via enzymatic cascade catalysis. Chinese Chemical Letters, 2024, 35(4): 108896-. doi: 10.1016/j.cclet.2023.108896
8. [8]
  Jing Cao , Dezheng Zhang , Bianqing Ren , Ping Song , Weilin Xu . Mn incorporated RuO₂ nanocrystals as an efficient and stable bifunctional electrocatalyst for oxygen evolution reaction and hydrogen evolution reaction in acid and alkaline. Chinese Chemical Letters, 2024, 35(10): 109863-. doi: 10.1016/j.cclet.2024.109863
9. [9]
  Ruilong Geng , Lingzi Peng , Chang Guo . Dynamic kinetic stereodivergent transformations of propargylic ammonium salts via dual nickel and copper catalysis. Chinese Chemical Letters, 2024, 35(8): 109433-. doi: 10.1016/j.cclet.2023.109433
10. [10]
  Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp³)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333
11. [11]
  Yuhao Guo , Na Li , Tingjiang Yan . Tandem catalysis for photoreduction of CO2 into multi-carbon fuels on atomically thin dual-metal phosphochalcogenides. Chinese Journal of Structural Chemistry, 2024, 43(7): 100320-100320. doi: 10.1016/j.cjsc.2024.100320
12. [12]
  Yi Luo , Lin Dong . Multicomponent remote C(sp²)-H bond addition by Ru catalysis: An efficient access to the alkylarylation of 2H-imidazoles. Chinese Chemical Letters, 2024, 35(10): 109648-. doi: 10.1016/j.cclet.2024.109648
13. [13]
  Weichen WANG , Chunhua GONG , Junyong ZHANG , Yanfeng BI , Hao XU , Jingli XIE . Construction of two metal-organic frameworks by rigid bis(triazole) and carboxylate mixed-ligands and their catalytic properties for CO₂ cycloaddition reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(7): 1377-1386. doi: 10.11862/CJIC.20230415
14. [14]
  Baokang Geng , Xiang Chu , Li Liu , Lingling Zhang , Shuaishuai Zhang , Xiao Wang , Shuyan Song , Hongjie Zhang . High-efficiency PdNi single-atom alloy catalyst toward cross-coupling reaction. Chinese Chemical Letters, 2024, 35(7): 108924-. doi: 10.1016/j.cclet.2023.108924
15. [15]
  Mengli Xu , Zhenmin Xu , Zhenfeng Bian . Achieving Ullmann coupling reaction via photothermal synergy with ultrafine Pd nanoclusters supported on mesoporous TiO2. Chinese Journal of Structural Chemistry, 2024, 43(7): 100305-100305. doi: 10.1016/j.cjsc.2024.100305
16. [16]
  Junchuan Sun , Lu Wang . Carbon exchange enabled supra-photothermal methane dry reforming. Chinese Journal of Structural Chemistry, 2024, 43(10): 100330-100330. doi: 10.1016/j.cjsc.2024.100330
17. [17]
  Zhigang Zeng , Changzhou Liao , Lei Yu . Molecules for COVID-19 treatment. Chinese Chemical Letters, 2024, 35(7): 109349-. doi: 10.1016/j.cclet.2023.109349
18. [18]
  Shuang Li , Jiayu Sun , Guocheng Liu , Shuo Zhang , Zhong Zhang , Xiuli Wang . A new Keggin-type polyoxometallate-based bifunctional catalyst for trace detection and pH-universal photodegradation of phenol. Chinese Chemical Letters, 2024, 35(8): 109148-. doi: 10.1016/j.cclet.2023.109148
19. [19]
  Xin Li , Xuan Ding , Junkun Zhou , Hui Shi , Zhenxi Dai , Jiayi Liu , Yongcun Ma , Penghui Shao , Liming Yang , Xubiao Luo . Utilizing synergistic effects of bifunctional polymer hydrogel PAM-PAMPS for selective capture of Pb(Ⅱ) from wastewater. Chinese Chemical Letters, 2024, 35(7): 109158-. doi: 10.1016/j.cclet.2023.109158
20. [20]
  Lingling Su , Qunyan Wu , Congzhi Wang , Jianhui Lan , Weiqun Shi . Theoretical design of polyazole based ligands for the separation of Am(Ⅲ)/Eu(Ⅲ). Chinese Chemical Letters, 2024, 35(8): 109402-. doi: 10.1016/j.cclet.2023.109402

Get Citation

PDF

XML

Metrics

PDF Downloads(1)
Abstract views(210)
HTML views(4)

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