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.
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