Journal Home > Volume 2 , Issue 2
Polyoxometalates 2023, 2(2): 9140024 https://doi.org/10.26599/POM.2023.9140024
Research Article | Open Access | Issue | Published: 03 March 2023

Silver-modified polyniobotungstate for the visible light-induced simultaneous cleavage of C–C and C–N bonds

Show Author's Information Shujun Li1 ( ),  Na Li1,  Gang Li1,  Yubin Ma1,  Mengyao Huang1,  Qingchun Xia1,  Qianyi Zhao1 ( ),  Xuenian Chen1,2 ( )
School of Chemistry and Chemical Engineering, Henan Key Laboratory of Boron Chemistry and Advanced Energy Materials, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Normal University, Xinxiang 453007, China
Green Catalysis Center and College of Chemistry, Zhengzhou University, Zhengzhou 450001, China
Keywords:
photocatalyst, polyoxometalates, polyniobotungstate, bond cleavage
Cite this article:
Li S, Li N, Li G, et al. Silver-modified polyniobotungstate for the visible light-induced simultaneous cleavage of C–C and C–N bonds. Polyoxometalates, 2023, 2(2): 9140024. https://doi.org/10.26599/POM.2023.9140024
Download citation
EndNote(RIS)
BibTeX

3082

Views

583

Downloads

Citations

11

Crossref

N/A

WoS

N/A

Scopus

N/A

CSCD

Abstract Full text Electronic supplementary material About this article

Silver-modified polyniobotungstate based on Nb/W mixed-addendum polyoxometalate with formula Ag9[P2W15Nb3O62]·21H2O (Ag-Nb/W) was synthesized and then characterized by various analytical and spectral techniques. Ag-Nb/W was proven to be an efficient photocatalyst for the oxidative ring opening of 2-phenylimidazo[1,2-a]pyridine via the simultaneous cleavage of C–C and C–N bonds. Under visible light (430–440 nm) and with oxygen as an oxidant at room temperature, Ag-Nb/W can catalyze the rapid transformation of various 2-phenylimidazo[1,2-a]pyridine derivatives to produce the corresponding oxidative ring-opening product N-(pyridin-2-yl) amides in good isolated yields ranging from 65% to 78%. As a heterogeneous photocatalyst, Ag-Nb/W showed excellent sustainability and recyclability in the recycling experiments. Infrared (IR) spectroscopy and X-ray diffraction (XRD) analysis indicated that Ag-Nb/W could retain its integrity after catalysis. A possible mechanism involving the singlet oxygen for the catalytic reaction was proposed.


menu
Abstract
Full text
Outline
Electronic supplementary material
About this article

Silver-modified polyniobotungstate for the visible light-induced simultaneous cleavage of C–C and C–N bonds

Show Author's information Shujun Li1 ( ), Na Li1, Gang Li1, Yubin Ma1, Mengyao Huang1, Qingchun Xia1, Qianyi Zhao1 ( ), Xuenian Chen1,2 ( )
School of Chemistry and Chemical Engineering, Henan Key Laboratory of Boron Chemistry and Advanced Energy Materials, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Normal University, Xinxiang 453007, China
Green Catalysis Center and College of Chemistry, Zhengzhou University, Zhengzhou 450001, China

Abstract

Silver-modified polyniobotungstate based on Nb/W mixed-addendum polyoxometalate with formula Ag9[P2W15Nb3O62]·21H2O (Ag-Nb/W) was synthesized and then characterized by various analytical and spectral techniques. Ag-Nb/W was proven to be an efficient photocatalyst for the oxidative ring opening of 2-phenylimidazo[1,2-a]pyridine via the simultaneous cleavage of C–C and C–N bonds. Under visible light (430–440 nm) and with oxygen as an oxidant at room temperature, Ag-Nb/W can catalyze the rapid transformation of various 2-phenylimidazo[1,2-a]pyridine derivatives to produce the corresponding oxidative ring-opening product N-(pyridin-2-yl) amides in good isolated yields ranging from 65% to 78%. As a heterogeneous photocatalyst, Ag-Nb/W showed excellent sustainability and recyclability in the recycling experiments. Infrared (IR) spectroscopy and X-ray diffraction (XRD) analysis indicated that Ag-Nb/W could retain its integrity after catalysis. A possible mechanism involving the singlet oxygen for the catalytic reaction was proposed.

Keywords: photocatalyst, polyoxometalates, polyniobotungstate, bond cleavage

References(52)

[1]

Pope, M. T.; Müller, A. Polyoxometalate chemistry: An old field with new dimensions in several disciplines. Angew. Chem., Int. Ed. 1991, 30, 34–48.
DOI Google Scholar
[2]

Long, D. L.; Tsunashima, R.; Cronin, L. Polyoxometalates: Building blocks for functional nanoscale systems. Angew. Chem., Int. Ed. 2010, 49, 1736–1758.
DOI Google Scholar
[3]

Zheng, S. T.; Yang, G. Y. Recent advances in paramagnetic-TM-substituted polyoxometalates (TM = Mn, Fe, Co, Ni, Cu). Chem. Soc. Rev. 2012, 41, 7623–7646.
DOI Google Scholar
[4]

Liu, J. C.; Wang, J. F.; Han, Q.; Shangguan, P.; Liu, L. L.; Chen, L. J.; Zhao, J. W.; Streb, C.; Song, Y. F. Multicomponent self-assembly of a giant heterometallic polyoxotungstate supercluster with antitumor activity. Angew. Chem., Int. Ed. 2021, 60, 11153–11157.
DOI Google Scholar
[5]

Yamase, T. Photo- and electrochromism of polyoxometalates and related materials. Chem. Rev. 1998, 98, 307–326.
DOI Google Scholar
[6]

Wang, S. S.; Yang, G. Y. Recent advances in polyoxometalate-catalyzed reactions. Chem. Rev. 2015, 115, 4893–4962.
DOI Google Scholar
[7]

Yang, G. P.; Li, K.; Hu, C. W. Recent advances in uranium-containing polyoxometalates. Inorg. Chem. Front. 2022, 9, 5408.
DOI Google Scholar
[8]

Lόpez, X.; Carbό, J. J.; Bo, C.; Poblet, J. M. Structure, properties and reactivity of polyoxometalates: A theoretical perspective. Chem. Soc. Rev. 2012, 41, 7537–7571.
DOI Google Scholar
[9]

Liu, Y.; Tang, C. S.; Cheng, M.; Chen, M.; Chen, S.; Lei, L.; Chen, Y. S.; Yi, H.; Fu, Y. K.; Li, L. Polyoxometalate@metal-organic framework composites as effective photocatalysts. ACS Catal. 2021, 11, 13374–13396.
DOI Google Scholar
[10]

Zhang, M.; Li, H. J.; Zhang, J. H.; Lv, H. J.; Yang, G. Y. Research advances of light-driven hydrogen evolution using polyoxometalate-based catalysts. Chin. J. Catal. 2021, 42, 855–871.
DOI Google Scholar
[11]

Li, S. J.; Liu, S. M.; Liu, S. X.; Liu, Y. W.; Tang, Q.; Shi, Z.; Ouyang, S. X.; Ye, J. H. {Ta12}/{Ta16} cluster-containing polytantalotungstates with remarkable photocatalytic H2 evolution activity. J. Am. Chem. Soc. 2012, 134, 19716–19721.
DOI Google Scholar
[12]

Zhang, M.; Xin, X.; Feng, Y. Q.; Zhang, J. H.; Lv, H. J.; Yang, G. Y. Coupling Ni-substituted polyoxometalate catalysts with water-soluble CdSe quantum dots for ultraefficient photogeneration of hydrogen under visible light. Appl. Catal. B Environ. 2022, 303, 120893.
DOI Google Scholar
[13]

Li, X. X.; Zhang, L.; Liu, J.; Yuan, L.; Wang, T.; Wang, J. Y.; Dong, L. Z.; Huang, K.; Lan, Y. Q. Design of crystalline reduction-oxidation cluster-based catalysts for artificial photosynthesis. JACS Au 2021, 1, 1288–1295.
DOI Google Scholar
[14]

Li, X. X.; Zhang, L.; Yuan, L.; Wang, T.; Dong, L. Z.; Huang, K.; Liu, J.; Lan, Y. Q. Constructing crystalline redox catalyst to achieve efficient CO2 photoreduction reaction in water vapor. Chem. Eng. J. 2022, 442, 136157.
DOI Google Scholar
[15]

Yao, S. J.; Li, N.; Liu, J.; Dong, L. Z.; Liu, J. J.; Xin, Z. F.; Li, D. S.; Li, S. L.; Lan, Y. Q. Ferrocene-functionalized crystalline biomimetic catalysts for efficient CO2 photoreduction. Inorg. Chem. 2022, 61, 2167–2173.
DOI Google Scholar
[16]

Gu, J.; Chen, W.; Shan, G. G.; Li, G.; Sun, C.; Wang, X. L.; Su, Z. The roles of polyoxometalates in photocatalytic reduction of carbon dioxide. Mater. Today Energy 2021, 21, 100760.
DOI Google Scholar
[17]

Lan, J.; Wang, Y.; Huang, B.; Xiao, Z. C.; Wu, P. F. Application of polyoxometalates in photocatalytic degradation of organic pollutants. Nanoscale Adv. 2021, 3, 4646–4658.
DOI Google Scholar
[18]

Lai, S. Y.; Ng, K. H.; Cheng, C. K.; Nur, H.; Nurhadi, M.; Arumugam, M. Photocatalytic remediation of organic waste over keggin-based polyoxometalate materials: A review. Chemosphere 2021, 263, 128244.
DOI Google Scholar
[19]

Li, H. L.; Zhang, M.; Lian, C.; Lang, Z. L.; Lv, H. J.; Yang, G. Y. Ring-shaped polyoxometalate built by {Mn4PW9} and PO4 units for efficient visible-light-driven hydrogen evolution. CCS Chem. 2021, 3, 2095–2103.
DOI Google Scholar
[20]

Xia, Z. N.; Wang, L. B.; Zhang, Q.; Li, F. Y.; Xu, L. Fast degradation of phenol over porphyrin-polyoxometalate composite photocatalysts under visible light. Polyoxometalates 2022, 1, 9140001.
DOI Google Scholar
[21]

Zang, D. J.; Wang, H. Q. Polyoxometalate-based nanostructures for electrocatalytic and photocatalytic CO2 reduction. Polyoxometalates 2022, 1, 9140006.
DOI Google Scholar
[22]

Yang, L.; Zhang, Z.; Zhang, C. N.; Li, S.; Liu, G. C.; Wang, X. L. An excellent multifunctional photocatalyst with a polyoxometalate-viologen framework for CEES oxidation, Cr(VI) reduction and dye decolorization under different light regimes. Inorg. Chem. Front. 2022, 9, 4824–4833.
DOI Google Scholar
[23]

Qin, K. J.; Zang, D. J.; Wei, Y. G. Polyoxometalates based compounds for green synthesis of aldehydes and ketones. Chin. Chem. Lett., in press, https://doi.org/10.1016/j.cclet.2022.107999.
DOI Google Scholar
[24]

Hiskia, A.; Mylonas, A.; Papaconstantinou, E. Comparison of the photoredox properties of polyoxometallates and semiconducting particles. Chem. Soc. Rev. 2001, 30, 62–69.
DOI Google Scholar
[25]

Suzuki, K.; Mizuno, N.; Yamaguchi, K. Polyoxometalate photocatalysis for liquid-phase selective organic functional group transformations. ACS Catal. 2018, 8, 10809–10825.
DOI Google Scholar
[26]

Streb, C.; Kastner, K.; Tucher, J. Polyoxometalates in photocatalysis. Phys. Sci. Rev. 2019, 4, 20170177.
DOI Google Scholar
[27]

Li, H. F.; Yang, M. N.; Yuan, Z. L.; Sun, Y. H.; Ma, P. T.; Niu, J. Y.; Wang, J. P. Construction of one Ru2W12-cluster and six lacunary Keggin tungstoarsenate leading to the larger Ru-containing polyoxometalate photocatalyst. Chin. Chem. Lett. 2022, 33, 4664–4668.
DOI Google Scholar
[28]

Ravelli, D.; Protti, S.; Fagnoni, M. Decatungstate anion for photocatalyzed “window ledge” reactions. Acc. Chem. Res. 2016, 49, 2232–2242.
DOI Google Scholar
[29]

Lykakis, I. N.; Tanielian, C.; Seghrouchni, R.; Orfanopoulos, M. Mechanism of decatungstate photocatalyzed oxygenation of aromatic alcohols: Part II. Kinetic isotope effects studies. J. Mol. Catal. A Chem. 2007, 262, 176–184.
DOI Google Scholar
[30]

Liu, Y.-F.; Hu, C.-W.; Yang, G.-P. Recent advances in polyoxometalates acid-catalyzed organic reactions. Chin. Chem. Lett., in press, https://doi.org/10.1016/j.cclet.2022.108097.
DOI Google Scholar
[31]

Huang, X. Q.; Liu, S.; Liu, G.; Tao, Y. W.; Wang, C. R.; Zhang, Y. L.; Li, Z.; Wang, H. W.; Zhou, Z.; Shen, G. D. et al. An unprecedented 2-fold interpenetrated lvt open framework built from Zn6 ring seamed trivacant polyoxotungstates used for photocatalytic synthesis of pyridine derivatives. Appl. Catal. B Environ. 2023, 323, 122134.
DOI Google Scholar
[32]

Gu, Y. Q.; Li, Q.; Zang, D. J.; Huang, Y. C.; Yu, H.; Wei, Y. G. Light-induced efficient hydroxylation of benzene to phenol by quinolinium and polyoxovanadate-based supramolecular catalysts. Angew. Chem., Int. Ed. 2021, 60, 13310–13316.
DOI Google Scholar
[33]

Ma, Y. B.; Gao, F.; Xiao, W. R.; Li, N.; Li, S. J.; Yu, B.; Chen, X. N. Two transition-metal-modified Nb/W mixed-addendum polyoxometalates for visible-light-mediated aerobic benzylic C-H oxidations. Chin. Chem. Lett. 2022, 33, 4395–4399.
DOI Google Scholar
[34]

Ryu, I.; Tani, A.; Fukuyama, T.; Ravelli, D.; Montanaro, S.; Fagnoni, M. Efficient C-H/C-N and C-H/C-CO-N conversion via decatungstate-photoinduced alkylation of diisopropyl azodicarboxylate. Org. Lett. 2013, 15, 2554–2557.
DOI Google Scholar
[35]

Li, S. J.; Li, G.; Ji, P. P.; Zhang, J. W.; Liu, S. X.; Zhang, J.; Chen, X. N. A giant Mo/Ta/W ternary mixed-addenda polyoxometalate with efficient photocatalytic activity for primary amine coupling. ACS Appl. Mater. Interfaces 2019, 11, 43287–43293.
DOI Google Scholar
[36]

Sarver , P. J.; Bacauanu , V.; Schultz , D. M.; DiRocco, D. A.; Lam, Y. H.; Sherer, E. C.; MacMillan, D. W. C. The merger of decatungstate and copper catalysis to enable aliphatic C(sp3)-H trifluoromethylation. Nat. Chem. 2020, 12, 459–467.
DOI Google Scholar
[37]

Jiao, J. C.; Yan, X. M.; Xing, S. Z.; Zhang, T.; Han, Q. X. Design of a polyoxometalate-based metal-organic framework for photocatalytic C(sp3)-H oxidation of toluene. Inorg. Chem. 2022, 61, 2421–2427.
DOI Google Scholar
[38]

Zhao, W. Z.; Zeng, X. H.; Huang, L.; Qiu, S. Q.; Xie, J. Y.; Yu, H.; Wei, Y. G. Oxidative dehydrogenation of hydrazines and diarylamines using a polyoxomolybdate-based iron catalyst. Chem. Commun. 2021, 57, 7677–7680.
DOI Google Scholar
[39]

Nodwell, M. B.; Yang, H.; Čolović, M.; Yuan, Z. L.; Merkens, H.; Martin, R. E.; Bénard, F.; Schaffer, P.; Britton, R. 18F-fluorination of unactivated C-H bonds in branched aliphatic amino acids: Direct synthesis of oncological positron emission tomography imaging agents. J. Am. Chem. Soc. 2017, 139, 3595–3598.
DOI Google Scholar
[40]

Chen, F.; Wang, T.; Jiao, N. Recent advances in transition-metal-catalyzed functionalization of unstrained carbon-carbon bonds. Chem. Rev. 2014, 114, 8613–8661.
DOI Google Scholar
[41]

Souillart, L.; Cramer, N. Catalytic C-C bond activations via oxidative addition to transition metals. Chem. Rev. 2015, 115, 9410–9464.
DOI Google Scholar
[42]

Yang, G. P.; Li, K.; Liu, W.; Zeng, K.; Liu, Y. F. Copper-catalyzed aerobic oxidative C-C bond cleavage of simple ketones for the synthesis of amides. Org. Biomol. Chem. 2020, 18, 6958–6964.
DOI Google Scholar
[43]

Chen, W. M.; Xie, X.; Zhang, J.; Qu, J.; Luo, C.; Lai, Y. Z.; Jiang, F.; Yu, H.; Wei, Y. G. Oxidative carbon-carbon bond cleavage of 1,2-diols to carboxylic acids/ketones by an inorganic-ligand supported iron catalyst. Green Chem. 2021, 23, 9140–9146.
DOI Google Scholar
[44]

Tang, C. H.; Jiao, N. Copper-catalyzed aerobic oxidative C-C bond cleavage for C-N bond formation: From ketones to amides. Angew. Chem., Int. Ed. 2014, 53, 6528–6532.
DOI Google Scholar
[45]

Ritu; Sharma, C.; Kumar, S.; Jain, N. Singlet oxygen mediated dual C-C and C-N bond cleavage in visible light. Org. Biomol. Chem. 2020, 18, 2921–2928.
DOI Google Scholar
[46]

Dreis, A. M.; Douglas, C. J. Catalytic carbon-carbon σ bond activation: An intramolecular carbo-acylation reaction with acylquinolines. J. Am. Chem. Soc. 2009, 131, 412–413.
DOI Google Scholar
[47]

Yan, K. L.; Yang, D. S.; Wei, W.; Li, G. Q.; Sun, M. Y.; Zhang, Q. Y.; Tian, L. J.; Wang, H. Metal-free TBHP-mediated oxidative ring openings of 2-arylimidazopyridines via regioselective cleavage of C-C and C-N bonds. RSC Adv. 2015, 5, 100102–100105.
DOI Google Scholar
[48]

Chen, Z. W.; Wen, X. W.; Qian, Y. P.; Liang, P.; Liu, B. T.; Ye, M. Ce(III)-catalyzed highly efficient synthesis of pyridyl benzamides from aminopyridines and nitroolefins without external oxidants. Org. Biomol. Chem. 2018, 16, 1247–1251.
DOI Google Scholar
[49]

Xu, F. Z.; Wang, Y. Y.; Xun, X. W.; Huang, Y.; Jin, Z. C.; Song, B. A.; Wu, J. Diverse oxidative C(sp2)-N bond cleavages of aromatic fused imidazoles for synthesis of α-ketoamides and N-(pyridin-2-yl)arylamides. J. Org. Chem. 2019, 84, 8411–8422.
DOI Google Scholar
[50]

Gong, J.; Chen, Y. G.; Qu, L. Y.; Liu, Q. Preparation and characterization of new peroxyniobium-containing phosphotungstates with Dawson structures. Polyhedron 1996, 15, 2273–2277.
DOI Google Scholar
[51]

Romand, M.; Roubin, M.; Deloume, J. P. ESCA studies of some copper and silver selenides. J. Electron Spectrosc. Relat. Phenom. 1978, 13, 229–242.
DOI Google Scholar
[52]

Kuznetsova, A. A.; Volchek, V. V.; Yanshole, V. V.; Fedorenko, A. D.; Kompankov, N. B.; Kokovkin, V. V.; Gushchin, A. L.; Abramov, P. A.; Sokolov, M. N. Coordination of Pt(IV) by {P8W48} macrocyclic inorganic cavitand: Structural, solution, and electrochemical studies. Inorg. Chem. 2022, 61, 14560–14567.
DOI Google Scholar
File
0024_ESM.pdf (5 MB)
0024_ESM_LG-20191018.cif (518 KB)
0024_ESM_checkcif.pdf (150.1 KB)
Publication history
Copyright
Acknowledgements
Rights and permissions

Publication history

Received: 22 November 2022
Revised: 06 January 2023
Accepted: 19 January 2023
Published: 03 March 2023
Issue date: June 2023

Copyright

© The Author(s) 2023. Polyoxometalates published by Tsinghua University Press.

Acknowledgements

Acknowledgements

This work was supported by the National Natural Science Foundation of China (Nos. 22171073 and U1804253) and the Program for Science & Technology Innovation Talents in Universities of Henan Province (No. 23HASTIT005).

Rights and permissions

The articles published in this open access journal are distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits use, distribution and reproduction in any medium, provided the original work is properly cited.

Return