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Nano Research Energy 2022, 1: 9120006 https://doi.org/10.26599/NRE.2022.9120006
Review Article | Open Access | Issue | Published: 12 May 2022

Control of selectivity in organic synthesis via heterogeneous photocatalysis under visible light

Show Author's Information Yitao Dai1,2( ),  Yujie Xiong2( )
Suzhou Institute for Advanced Research, University of Science and Technology of China, Suzhou 215123, China
School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, China
Keywords:
visible light irradiation, organic synthesis, heterogeneous photocatalysis, selectivity control, photocatalyst design
Cite this article:
Dai Y, Xiong Y. Control of selectivity in organic synthesis via heterogeneous photocatalysis under visible light. Nano Research Energy, 2022, 1: 9120006. https://doi.org/10.26599/NRE.2022.9120006
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Abstract Full text About this article

Organic synthesis driven by heterogeneous catalysis is a central research theme to both fundamental research and industrial production of fine chemicals. However, the employment of stoichiometric strong oxidizing or reducing reagents (e.g., K2Cr2O7 and LiAlH4) and harsh reaction conditions (e.g., high temperature and pressure) always leads to the products of overreaction and other by-product residues (e.g., salt and acid waste). Thus the poor control of product selectivity and tremendous energy consumption result in the urgent demand to develop novel technologies for heterogeneous catalysis. Given the current global theme of development in CO2 reduction and sustainable energy utilization, one promising protocol is heterogeneous photocatalysis. It enables sustainable solar-to-chemical energy conversion under mild conditions (e.g., room temperature, ambient pressure, and air as the oxidant) and offers unique reaction pathways for improved selectivity control. To accurately tailor the selectivity of desired products, the electronic structure (e.g., positions of valence-band maximum and conduction-band minimum), geometric structure (e.g., nanorod, nanosheet, and porous morphology), and surface chemical micro-environment (e.g., vacancy sites and co-catalysts) of heterogeneous photocatalysts require rational design and construction. In this review, we will briefly analyze some effective photocatalytic systems with the excellent regulation ability of product selectivity in organic transformations (mainly oxidation and reduction types) under visible light irradiation, and put forward opinions on the optimal fabrication of nanostructured photocatalysts to realize selective organic synthesis.


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About this article

Control of selectivity in organic synthesis via heterogeneous photocatalysis under visible light

Show Author's information Yitao Dai1,2( ), Yujie Xiong2( )
Suzhou Institute for Advanced Research, University of Science and Technology of China, Suzhou 215123, China
School of Chemistry and Materials Science, University of Science and Technology of China, Hefei 230026, China

Abstract

Organic synthesis driven by heterogeneous catalysis is a central research theme to both fundamental research and industrial production of fine chemicals. However, the employment of stoichiometric strong oxidizing or reducing reagents (e.g., K2Cr2O7 and LiAlH4) and harsh reaction conditions (e.g., high temperature and pressure) always leads to the products of overreaction and other by-product residues (e.g., salt and acid waste). Thus the poor control of product selectivity and tremendous energy consumption result in the urgent demand to develop novel technologies for heterogeneous catalysis. Given the current global theme of development in CO2 reduction and sustainable energy utilization, one promising protocol is heterogeneous photocatalysis. It enables sustainable solar-to-chemical energy conversion under mild conditions (e.g., room temperature, ambient pressure, and air as the oxidant) and offers unique reaction pathways for improved selectivity control. To accurately tailor the selectivity of desired products, the electronic structure (e.g., positions of valence-band maximum and conduction-band minimum), geometric structure (e.g., nanorod, nanosheet, and porous morphology), and surface chemical micro-environment (e.g., vacancy sites and co-catalysts) of heterogeneous photocatalysts require rational design and construction. In this review, we will briefly analyze some effective photocatalytic systems with the excellent regulation ability of product selectivity in organic transformations (mainly oxidation and reduction types) under visible light irradiation, and put forward opinions on the optimal fabrication of nanostructured photocatalysts to realize selective organic synthesis.

Keywords: visible light irradiation, organic synthesis, heterogeneous photocatalysis, selectivity control, photocatalyst design

References(163)

[1]
Taber, D. F. Oxidation and reduction in organic synthesis. In Organic Synthesis: State of the Art 2005-2007. Taber, D. F., Ed.; John Wiley & Sons, Inc. : Hoboken, 2008; pp 143-144.
[2]
Smith, M. B. Functional group exchange reactions: Oxidations. In Organic Synthesis. Smith, M. B., Ed.; 4th ed. Academic Press: Boston, 2017; pp 215-307.
[3]
Smith, M. B. Functional group exchange reactions: Reductions. In Organic Synthesis. Smith, M. B., Ed.; 4th ed. Academic Press: Boston, 2017; pp 309-418.
[4]
van Santen, R. A. Heterogeneous catalysis. In Modern Heterogeneous Catalysis: An Introduction. van Santen, R. A., Ed.; Wiley-VCH Verlag GmbH & Co. KgaA: Weinheim, 2017; pp 1-13.
[5]

Vogt, C.; Weckhuysen, B. M. The concept of active site in heterogeneous catalysis. Nat. Rev. Chem. 2022, 6, 89-111.
DOI Google Scholar
[6]

Guo, J.; Qin, Y. T.; Zhu, Y. F.; Zhang, X. F.; Long, C.; Zhao, M. T.; Tang, Z. Y. Metal-organic frameworks as catalytic selectivity regulators for organic transformations. Chem. Soc. Rev. 2021, 50, 5366-5396.
DOI Google Scholar
[7]

Grant, J. T.; Carrero, C. A.; Goeltl, F.; Venegas, J.; Mueller, P.; Burt, S. P.; Specht, S. E.; McDermott, W. P.; Chieregato, A.; Hermans, I. Selective oxidative dehydrogenation of propane to propene using boron nitride catalysts. Science 2016, 354, 1570-1573.
DOI Google Scholar
[8]

Lian, Z.; Si, C. W.; Jan, F.; Zhi, S. K.; Li, B. Coke deposition on Pt-based catalysts in propane direct dehydrogenation: Kinetics, suppression, and elimination. ACS Catal. 2021, 11, 9279-9292.
DOI Google Scholar
[9]

Zhang, Z. H.; Huber, G. W. Catalytic oxidation of carbohydrates into organic acids and furan chemicals. Chem. Soc. Rev. 2018, 47, 1351-1390.
DOI Google Scholar
[10]

Teong, S. P.; Yi, G. S.; Zhang, Y. G. Hydroxymethylfurfural production from bioresources: Past, present and future. Green Chem. 2014, 16, 2015-2026.
DOI Google Scholar
[11]

Rajendran, S.; Raghunathan, R.; Hevus, I.; Krishnan, R.; Ugrinov, A.; Sibi, M. P.; Webster, D. C.; Sivaguru, J. Programmed photodegradation of polymeric/oligomeric materials derived from renewable bioresources. Angew. Chem., Int. Ed. 2015, 54, 1159-1163.
DOI Google Scholar
[12]

Hopkins, K. T.; Wilson, W. D.; Bender, B. C.; McCurdy, D. R.; Hall, J. E.; Tidwell, R. R.; Kumar, A.; Bajic, M.; Boykin, D. W. Extended aromatic furan amidino derivatives as anti-Pneumocystis carinii agents. J. Med. Chem. 1998, 41, 3872-3878.
DOI Google Scholar
[13]

Braisted, A. C.; Oslob, J. D.; Delano, W. L.; Hyde, J.; McDowell, R. S.; Waal, N.; Yu, C.; Arkin, M. R.; Raimundo, B. C. Discovery of a potent small molecule IL-2 inhibitor through fragment assembly. J. Am. Chem. Soc. 2003, 125, 3714-3715.
DOI Google Scholar
[14]

Liu, H.; Cao, X. J.; Wei, J. N.; Jia, W. L.; Li, M. Z.; Tang, X.; Zeng, X. H.; Sun, Y.; Lei, T. Z.; Liu, S. J. et al. Efficient aerobic oxidation of 5-hydroxymethylfurfural to 2, 5-diformylfuran over Fe2O3-promoted MnO2 catalyst. ACS Sustainable Chem. Eng. 2019, 7, 7812-7822.
DOI Google Scholar
[15]

Hirai, H. Oligomers from hydroxymethylfurancarboxylic acid. J. Macromol. Sci. : Part A - Chem. 1984, 21, 1165-1179.
DOI Google Scholar
[16]

Antonyraj, C. A.; Kim, B.; Kim, Y.; Shin, S.; Lee, K. Y.; Kim, I.; Cho, J. K. Heterogeneous selective oxidation of 5-hydroxymethyl- 2-furfural (HMF) into 2, 5-diformylfuran catalyzed by vanadium supported activated carbon in MIBK, extracting solvent for HMF. Catal. Commun. 2014, 57, 64-68.
DOI Google Scholar
[17]

Nie, J. F.; Xie, J. H.; Liu, H. C. Efficient aerobic oxidation of 5-hydroxymethylfurfural to 2, 5-diformylfuran on supported Ru catalysts. J. Catal. 2013, 301, 83-91.
DOI Google Scholar
[18]

Neaţu, F.; Petrea, N.; Petre, R.; Somoghi, V.; Florea, M.; Parvulescu, V. I. Oxidation of 5-hydroxymethyl furfural to 2, 5-diformylfuran in aqueous media over heterogeneous manganese based catalysts. Catal. Today 2016, 278, 66-73.
DOI Google Scholar
[19]

Siyo, B.; Schneider, M.; Radnik, J.; Pohl, M. M.; Langer, P.; Steinfeldt, N. Influence of support on the aerobic oxidation of HMF into FDCA over preformed Pd nanoparticle based materials. Appl. Catal. A: Gen. 2014, 478, 107-116.
DOI Google Scholar
[20]

Sahu, R.; Dhepe, P. L. Synthesis of 2, 5-furandicarboxylic acid by the aerobic oxidation of 5-hydroxymethyl furfural over supported metal catalysts. React. Kinet. Mech. Catal. 2014, 112, 173-187.
DOI Google Scholar
[21]

Gorbanev, Y. Y.; Klitgaard, S. K.; Woodley, J. M.; Christensen, C. H.; Riisager, A. Gold-catalyzed aerobic oxidation of 5-hydroxymethylfurfural in water at ambient temperature. ChemSusChem 2009, 2, 672-675.
DOI Google Scholar
[22]

Salak Asghari, F.; Yoshida, H. Acid-catalyzed production of 5-hydroxymethyl furfural from d-fructose in subcritical water. Ind. Eng. Chem. Res. 2006, 45, 2163-2173.
DOI Google Scholar
[23]

Formenti, D.; Ferretti, F.; Scharnagl, F. K.; Beller, M. Reduction of nitro compounds using 3D-non-noble metal catalysts. Chem. Rev. 2019, 119, 2611-2680.
DOI Google Scholar
[24]

Zhao, J. X.; Chen, C. Q.; Xing, C. H.; Jiao, Z. F.; Yu, M. T.; Mei, B. B.; Yang, J.; Zhang, B. Y.; Jiang, Z.; Qin, Y. Selectivity regulation in Au-catalyzed nitroaromatic hydrogenation by anchoring single-site metal oxide promoters. ACS Catal. 2020, 10, 2837-2844.
DOI Google Scholar
[25]

Zhang, M.; Liu, Q.; Sun, L. B.; Su, H. J.; Qi, C. X. Synthesis of high efficient and stable Au@ZIF-8 with difference particle size for chemselective hydrogenation of nitro compounds. Catal. Lett. 2020, 150, 438-449.
DOI Google Scholar
[26]

Bae, S.; Gim, S.; Kim, H.; Hanna, K. Effect of NaBH4 on properties of nanoscale zero-valent iron and its catalytic activity for reduction of p-nitrophenol. Appl. Catal. B: Environ. 2016, 182, 541-549.
DOI Google Scholar
[27]

Moghaddam, M. M.; Pieber, B.; Glasnov, T.; Kappe, C. O. Immobilized iron oxide nanoparticles as stable and reusable catalysts for hydrazine-mediated nitro reductions in continuous flow. ChemSusChem 2014, 7, 3122-3131.
DOI Google Scholar
[28]

Jagadeesh, R. V.; Surkus, A. E.; Junge, H.; Pohl, M. M.; Radnik, J.; Rabeah, J.; Huan, H. M.; Schünemann, V.; Brückner, A.; Beller, M. Nanoscale Fe2O3-based catalysts for selective hydrogenation of nitroarenes to anilines. Science 2013, 342, 1073-1076.
DOI Google Scholar
[29]

Duan, Y. N.; Dong, X. S.; Song, T.; Wang, Z. Z.; Xiao, J. L.; Yuan, Y. Z.; Yang, Y. Hydrogenation of functionalized nitroarenes catalyzed by single-phase pyrite FeS2 nanoparticles on N, S-codoped porous carbon. ChemSusChem 2019, 12, 4636-4644.
DOI Google Scholar
[30]

Thombal, P. R.; Rao, K. M.; Zo, S.; Narayanan, K. B.; Thombal, R. S.; Han, S. S. Efficient metal-free catalytic reduction of nitro to amine over carbon sheets doped with nitrogen. Catal. Lett. 2022, 152, 538-546.
DOI Google Scholar
[31]

Lang, X. J.; Chen, X. D.; Zhao, J. C. Heterogeneous visible light photocatalysis for selective organic transformations. Chem. Soc. Rev. 2014, 43, 473-486.
DOI Google Scholar
[32]

Schultz, D. M.; Yoon, T. P. Solar synthesis: Prospects in visible light photocatalysis. Science 2014, 343, 1239176.
DOI Google Scholar
[33]

Friedmann, D.; Hakki, A.; Kim, H.; Choi, W.; Bahnemann, D. Heterogeneous photocatalytic organic synthesis: State-of-the-art and future perspectives. Green Chem. 2016, 18, 5391-5411.
DOI Google Scholar
[34]

Luo, N. C.; Montini, T.; Zhang, J.; Fornasiero, P.; Fonda, E.; Hou, T. T.; Nie, W.; Lu, J. M.; Liu, J. X.; Heggen, M. et al. Visible-light-driven coproduction of diesel precursors and hydrogen from lignocellulose- derived methylfurans. Nat. Energy 2019, 4, 575-584.
DOI Google Scholar
[35]

Gisbertz, S.; Pieber, B. Heterogeneous Photocatalysis in Organic Synthesis. ChemPhotoChem 2020, 4, 456-475.
DOI Google Scholar
[36]

Filippini, G.; Longobardo, F.; Forster, L.; Criado, A.; Di Carmine, G.; Nasi, L.; D'Agostino, C.; Melchionna, M.; Fornasiero, P.; Prato, M. Light-driven, heterogeneous organocatalysts for C-C bond formation toward valuable perfluoroalkylated intermediates. Sci. Adv. 2020, 6, eabc9923.
DOI Google Scholar
[37]

Longobardo, F.; Gentile, G.; Criado, A.; Actis, A.; Colussi, S.; Dal Santo, V.; Chiesa, M.; Filippini, G.; Fornasiero, P.; Prato, M. et al. Tailored amorphization of graphitic carbon nitride triggers superior photocatalytic C-C coupling towards the synthesis of perfluoroalkyl derivatives. Mater. Chem. Front. 2021, 5, 7267-7275.
DOI Google Scholar
[38]

Lam, E.; Reisner, E. A TiO2-Co(terpyridine)2 photocatalyst for the selective oxidation of cellulose to formate coupled to the reduction of CO2 to syngas. Angew. Chem., Int. Ed. 2021, 60, 23306-23312.
DOI Google Scholar
[39]

Rosso, C.; Filippini, G.; Criado, A.; Melchionna, M.; Fornasiero, P.; Prato, M. Metal-free photocatalysis: Two-dimensional nanomaterial connection toward advanced organic synthesis. ACS Nano 2021, 15, 3621-3630.
DOI Google Scholar
[40]

Cao, X.; Chen, Z.; Lin, R.; Cheong, W. C.; Liu, S. J.; Zhang, J.; Peng, Q.; Chen, C.; Han, T.; Tong, X. J. et al. A photochromic composite with enhanced carrier separation for the photocatalytic activation of benzylic C-H bonds in toluene. Nat. Catal. 2018, 1, 704-710.
DOI Google Scholar
[41]

Dai, Y. T.; Poidevin, C.; Ochoa-Hernández, C.; Auer, A. A.; Tüysüz, H. A supported bismuth halide perovskite photocatalyst for selective aliphatic and aromatic C-H bond activation. Angew. Chem., Int. Ed. 2020, 59, 5788-5796.
DOI Google Scholar
[42]

Dai, Y. T.; Li, C.; Shen, Y. B.; Lim, T.; Xu, J.; Li, Y. W.; Niemantsverdriet, H.; Besenbacher, F.; Lock, N.; Su, R. Light-tuned selective photosynthesis of azo- and azoxy-aromatics using graphitic C3N4. Nat. Commun. 2018, 9, 60.
DOI Google Scholar
[43]

Dai, Y. T.; Li, C.; Shen, Y. B.; Zhu, S. J.; Hvid, M. S.; Wu, L. C.; Skibsted, J.; Li, Y. W.; Niemantsverdriet, J. W. H.; Besenbacher, F. et al. Efficient solar-driven hydrogen transfer by bismuth-based photocatalyst with engineered basic sites. J. Am. Chem. Soc. 2018, 140, 16711-16719.
DOI Google Scholar
[44]

Li, X. B.; Xin, Z. K.; Xia, S. G.; Gao, X. Y.; Tung, C. H.; Wu, L. Z. Semiconductor nanocrystals for small molecule activation via artificial photosynthesis. Chem. Soc. Rev. 2020, 49, 9028-9056.
DOI Google Scholar
[45]

Fujishima, A.; Honda, K. Electrochemical photolysis of water at a semiconductor electrode. Nature 1972, 238, 37-38.
DOI Google Scholar
[46]

Shi, X. F.; Zhang, J. H.; Cui, G. W.; Deng, N.; Wang, W.; Wang, Q.; Tang, B. Photocatalytic H2 evolution improvement for H free-radical stabilization by electrostatic interaction of a Cu-BTC MOF with ZnO/GO. Nano Res. 2018, 11, 979-987.
DOI Google Scholar
[47]

Duan, J. Y.; Shi, W. D.; Xu, L. L.; Mou, G. Y.; Xin, Q. L.; Guan, J. G. Hierarchical nanostructures of fluorinated and naked Ta2O5 single crystalline nanorods: Hydrothermal preparation, formation mechanism and photocatalytic activity for H2 production. Chem. Commun. 2012, 48, 7301-7303.
DOI Google Scholar
[48]

Wang, L. N.; Shi, X. Q.; Jia, Y. F.; Cheng, H. F.; Wang, L.; Wang, Q. Z. Recent advances in bismuth vanadate-based photocatalysts for photoelectrochemical water splitting. Chin. Chem. Lett. 2021, 32, 1869-1878.
DOI Google Scholar
[49]

Deng, C. H.; Ye, F.; Wang, T.; Ling, X. H.; Peng, L. L.; Yu, H.; Ding, K. Z.; Hu, H. M.; Dong, Q.; Le, H. R. et al. Developing hierarchical CdS/NiO hollow heterogeneous architectures for boosting photocatalytic hydrogen generation. Nano Res. 2022, 15, 2003-2012.
DOI Google Scholar
[50]

Wang, X. C.; Maeda, K.; Thomas, A.; Takanabe, K.; Xin, G.; Carlsson, J. M.; Domen, K.; Antonietti, M. A metal-free polymeric photocatalyst for hydrogen production from water under visible light. Nat. Mater. 2009, 8, 76-80.
DOI Google Scholar
[51]

Hara, M.; Hitoki, G.; Takata, T.; Kondo, J. N.; Kobayashi, H.; Domen, K. TaON and Ta3N5 as new visible light driven photocatalysts. Catal. Today 2003, 78, 555-560.
DOI Google Scholar
[52]

Hoffmann, M. R.; Martin, S. T.; Choi, W.; Bahnemann, D. W. Environmental applications of semiconductor photocatalysis. Chem. Rev. 1995, 95, 69-96.
DOI Google Scholar
[53]

Long, R.; Li, Y.; Song, L.; Xiong, Y. J. Coupling solar energy into reactions: Materials design for surface plasmon-mediated catalysis. Small 2015, 11, 3873-3889.
DOI Google Scholar
[54]

Ye, W.; Long, R.; Huang, H.; Xiong, Y. J. Plasmonic nanostructures in solar energy conversion. J. Mater. Chem. C 2017, 5, 1008-1021.
DOI Google Scholar
[55]

Linic, S.; Christopher, P.; Ingram, D. B. Plasmonic-metal nanostructures for efficient conversion of solar to chemical energy. Nat. Mater. 2011, 10, 911-921.
DOI Google Scholar
[56]

Chen, X.; Zhu, H. Y.; Zhao, J. C.; Zheng, Z. F.; Gao, X. P. Visible-light-driven oxidation of organic contaminants in air with gold nanoparticle catalysts on oxide supports. Angew. Chem., Int. Ed. 2008, 47, 5353-5356.
DOI Google Scholar
[57]

Wang, P.; Huang, B. B.; Qin, X. Y.; Zhang, X. Y.; Dai, Y.; Wei, J. Y.; Whangbo, M. H. Ag@AgCl: A highly efficient and stable photocatalyst active under visible light. Angew. Chem., Int. Ed. 2008, 47, 7931- 7933.
DOI Google Scholar
[58]

Ahlawat, M.; Mittal, D.; Rao, V. G. Plasmon-induced hot-hole generation and extraction at nano-heterointerfaces for photocatalysis. Commun. Mater. 2021, 2, 114.
DOI Google Scholar
[59]

Li, J.; Lou, Z. Z.; Li, B. J. Nanostructured materials with localized surface plasmon resonance for photocatalysis. Chin. Chem. Lett. 2022, 33, 1154-1168.
DOI Google Scholar
[60]

Xiong, L. Q.; Tang, J. W. Strategies and challenges on selectivity of photocatalytic oxidation of organic substances. Adv. Energy Mater. 2021, 11, 2003216.
DOI Google Scholar
[61]

Valenzuela, M. A.; Albiter, E.; Ríos-Bernÿ, O.; Córdova, I.; Flores, S. O. Photocatalytic reduction of organic compounds. J. Adv. Oxid. Technol. 2010, 13, 321-340.
Google Scholar
[62]

Stroyuk, O. L.; Kuchmy, S. Y. Heterogeneous photocatalytic selective reductive transformations of organic compounds: A review. Theor. Exp. Chem. 2020, 56, 143-173.
DOI Google Scholar
[63]

Nosaka, Y.; Nosaka, A. Y. Generation and detection of reactive oxygen species in photocatalysis. Chem. Rev. 2017, 117, 11302-11336.
DOI Google Scholar
[64]

Sarina, S.; Zhu, H. Y.; Jaatinen, E.; Xiao, Q.; Liu, H. W.; Jia, J. F.; Chen, C.; Zhao, J. Enhancing catalytic performance of palladium in gold and palladium alloy nanoparticles for organic synthesis reactions through visible light irradiation at ambient temperatures. J. Am. Chem. Soc. 2013, 135, 5793-5801.
DOI Google Scholar
[65]

Wu, D.; Li, Z. Y.; Qi, Z. M.; Hu, S. W.; Long, R.; Song, L.; Xiong, Y. J. Boosting photocatalytic activity in cross-coupling reactions by constructing pd-oxide heterostructures. ChemNanoMat 2020, 6, 920-924.
DOI Google Scholar
[66]

Zhu, X. L.; Lin, Y. X.; Sun, Y.; Beard, M. C.; Yan, Y. Lead-halide perovskites for photocatalytic α-alkylation of aldehydes. J. Am. Chem. Soc. 2019, 141, 733-738.
DOI Google Scholar
[67]

Dai, Y. T.; Tüysüz, H. Lead-free Cs3Bi2Br9 perovskite as photocatalyst for ring-opening reactions of epoxides. ChemSusChem 2019, 12, 2587-2592.
DOI Google Scholar
[68]

Duan, M. L.; Hu, C. Y.; Duan, D. L.; Chen, R. T.; Wang, C. M.; Wu, D.; Xia, T.; Liu, H. J.; Dai, Y. T.; Long, R. et al. ppm-level Cu dopant on ultrathin Pd nanosheets/TiO2 for highly enhanced photocatalytic alcoholysis of epoxides. Appl. Catal. B: Environ. 2022, 307, 121211.
DOI Google Scholar
[69]

Zhao, Y. B.; Antonietti, M. Visible-light-irradiated graphitic carbon nitride photocatalyzed diels-alder reactions with dioxygen as sustainable mediator for photoinduced electrons. Angew. Chem., Int. Ed. 2017, 56, 9336-9340.
DOI Google Scholar
[70]

Huang, Z. P.; Zhao, Z. T.; Zhang, C. F.; Lu, J. M.; Liu, H. F.; Luo, N. C.; Zhang, J.; Wang, F. Enhanced photocatalytic alkane production from fatty acid decarboxylation via inhibition of radical oligomerization. Nat. Catal. 2020, 3, 170-178.
DOI Google Scholar
[71]

Han, Y. Z.; Huang, H.; Zhang, H. C.; Liu, Y.; Han, X.; Liu, R. H.; Li, H. T.; Kang, Z. H. Carbon quantum dots with photoenhanced hydrogen-bond catalytic activity in aldol condensations. ACS Catal. 2014, 4, 781-787.
DOI Google Scholar
[72]

Zhang, Y. H.; Zhang, N.; Tang, Z. R.; Xu, Y. J. Transforming CdS into an efficient visible light photocatalyst for selective oxidation of saturated primary C-H bonds under ambient conditions. Chem. Sci. 2012, 3, 2812-2822.
DOI Google Scholar
[73]

Zhang, Z. Z.; Yang, Y. Y.; Wang, Y. Y.; Yang, L. L.; Li, Q.; Chen, L. X.; Xu, D. S. Revealing the A-site effect of lead-free A3Sb2Br9 perovskite in photocatalytic C(sp3)-H bond activation. Angew. Chem., Int. Ed. 2020, 59, 18136-18139.
DOI Google Scholar
[74]

Guo, X. N.; Hao, C. H.; Jin, G. Q.; Zhu, H. Y.; Guo, X. Y. Copper nanoparticles on graphene support: An efficient photocatalyst for coupling of nitroaromatics in visible light. Angew. Chem., Int. Ed. 2014, 53, 1973-1977.
DOI Google Scholar
[75]

Wang, H.; Wang, L.; Zhang, J.; Wang, C. T.; Liu, Z. Y.; Gao, X. H.; Meng, X. J.; Yoo, S. J.; Kim, J. G.; Zhang, W. et al. Interfacial CoOx layers on TiO2 as an efficient catalyst for solvent-free aerobic oxidation of hydrocarbons. ChemSusChem 2018, 11, 3965-3974.
DOI Google Scholar
[76]

bin Saiman, M. I.; Brett, G. L.; Tiruvalam, R.; Forde, M. M.; Sharples, K.; Thetford, A.; Jenkins, R. L.; Dimitratos, N.; Lopez-Sanchez, J. A.; Murphy, D. M. et al. Involvement of surface-bound radicals in the oxidation of toluene using supported Au-Pd nanoparticles. Angew. Chem., Int. Ed. 2012, 51, 5981-5985.
DOI Google Scholar
[77]

Yuan, R. S.; Fan, S. L.; Zhou, H. X.; Ding, Z. X.; Lin, S.; Li, Z. H.; Zhang, Z. Z.; Xu, C.; Wu, L.; Wang, X. X. et al. Chlorine-radical-mediated photocatalytic activation of C-H bonds with visible light. Angew. Chem., Int. Ed. 2013, 52, 1035-1039.
DOI Google Scholar
[78]

Liu, Y.; Chen, L.; Yuan, Q.; He, J.; Au, C. T.; Yin, S. F. A green and efficient photocatalytic route for the highly-selective oxidation of saturated alpha-carbon C-H bonds in aromatic alkanes over flower-like Bi2WO6. Chem. Commun. 2016, 52, 1274-1277.
DOI Google Scholar
[79]

Huang, H. W.; Yuan, H. F.; Zhao, J. W.; Solís-Fernández, G.; Zhou, C.; Seo, J. W.; Hendrix, J.; Debroye, E.; Steele, J. A.; Hofkens, J. et al. C(sp3)-H bond activation by perovskite solar photocatalyst cell. ACS Energy Lett. 2019, 4, 203-208.
DOI Google Scholar
[80]

Huang, Y.; Liu, C. B.; Li, M. Y.; Li, H. Z.; Li, Y. W.; Su, R.; Zhang, B. Photoimmobilized Ni clusters boost photodehydrogenative coupling of amines to imines via enhanced hydrogen evolution kinetics. ACS Catal. 2020, 10, 3904-3910.
DOI Google Scholar
[81]

Okunaka, S.; Tokudome, H.; Hitomi, Y. Selective oxidation of toluene to benzaldehyde over Pd/BiVO4 particles under blue to green light irradiation. J. Catal. 2020, 391, 480-484.
DOI Google Scholar
[82]

Pahari, S. K.; Doong, R. A. Few-layered phosphorene-graphitic carbon nitride nanoheterostructure as a metal-free photocatalyst for aerobic oxidation of benzyl alcohol and toluene. ACS Sustainable Chem. Eng. 2020, 8, 13342-13351.
DOI Google Scholar
[83]

Dai, Y. T.; Tüysüz, H. Rapid acidic media growth of Cs3Bi2Br9 halide perovskite platelets for photocatalytic toluene oxidation. Sol. RRL 2021, 5, 2100265.
DOI Google Scholar
[84]

Pahari, S. K.; Pal, P.; Srivastava, D. N.; Ghosh, S. C.; Panda, A. B. Efficient photocatalytic selective nitro-reduction and C-H bond oxidation over ultrathin sheet mediated CdS flowers. Chem. Commun. 2015, 51, 10322-10325.
DOI Google Scholar
[85]

Li, Z.; Zhang, M.; Xin, X.; Lv, H. J. Mechanistic studies on the photooxidation of 5-hydroxymethylfurfural by polyoxometalate catalysts and atmospheric oxygen. ChemCatChem 2021, 13, 1389-1395.
DOI Google Scholar
[86]

Li, C. C.; Na, Y. Recent advances in photocatalytic oxidation of 5-hydroxymethylfurfural. ChemPhotoChem 2021, 5, 502-511.
DOI Google Scholar
[87]

Xu, S.; Zhou, P.; Zhang, Z. H.; Yang, C. J.; Zhang, B. G.; Deng, K. J.; Bottle, S.; Zhu, H. Y. Selective oxidation of 5-hydroxymethylfurfural to 2, 5-furandicarboxylic acid using O2 and a photocatalyst of Co-thioporphyrazine bonded to g-C3N4. J. Am. Chem. Soc. 2017, 139, 14775-14782.
DOI Google Scholar
[88]

Iqbal, N.; Choi, S.; You, Y. M.; Cho, E. J. Aerobic oxidation of aldehydes by visible light photocatalysis. Tetrahedron Lett. 2013, 54, 6222-6225.
DOI Google Scholar
[89]

Chen, Y. Z.; Wang, Z. U.; Wang, H. W.; Lu, J. L.; Yu, S. H.; Jiang, H. L. Singlet oxygen-engaged selective photo-oxidation over Pt nanocrystals/porphyrinic MOF: The roles of photothermal effect and Pt electronic state. J. Am. Chem. Soc. 2017, 139, 2035-2044.
DOI Google Scholar
[90]

Khan, A.; Goepel, M.; Kubas, A.; Łomot, D.; Lisowski, W.; Lisovytskiy, D.; Nowicka, A.; Colmenares, J. C.; Gläser, R. Selective oxidation of 5-hydroxymethylfurfural to 2, 5-diformylfuran by visible light-driven photocatalysis over in situ substrate-sensitized titania. ChemSusChem 2021, 14, 1351-1362.
DOI Google Scholar
[91]

Xue, J. J.; Huang, C. J.; Zong, Y. Q.; Gu, J. D.; Wang, M. X.; Ma, S. S. Fe(Ⅲ)-grafted Bi2MoO6 nanoplates for enhanced photocatalytic activities on tetracycline degradation and HMF oxidation. Appl. Organomet. Chem. 2019, 33, e5187.
Google Scholar
[92]

DiMeglio, J. L.; Breuhaus-Alvarez, A. G.; Li, S. Q.; Bartlett, B. M. Nitrate-mediated alcohol oxidation on cadmium sulfide photocatalysts. ACS Catal. 2019, 9, 5732-5741.
DOI Google Scholar
[93]

Zhou, B. W.; Song, J. L.; Zhang, Z. R.; Jiang, Z. W.; Zhang, P.; Han, B. X. Highly selective photocatalytic oxidation of biomass-derived chemicals to carboxyl compounds over Au/TiO2. Green Chem. 2017, 19, 1075-1081.
DOI Google Scholar
[94]
Zhang, W. Z.; Li, X. X.; Liu, S. R.; Qiu, J. H.; An, J. H.; Yao, J. F.; Zuo, S. L.; Zhang, B.; Xia, H. A.; Li, C. Z. Photocatalytic oxidation of 5-hydroxymethylfurfural over interfacial-enhanced Ag/TiO2 under visible light irradiation. ChemSusChem, in press, http://doi.org/10.1002/cssc.202102158.
[95]

Ma, B.; Wang, Y. Y.; Guo, X. N.; Tong, X. L.; Liu, C.; Wang, Y. W.; Guo, X. Y. Photocatalytic synthesis of 2, 5-diformylfuran from 5-hydroxymethyfurfural or fructose over bimetallic Au-Ru nanoparticles supported on reduced graphene oxides. Appl. Catal. A: Gen. 2018, 552, 70-76.
DOI Google Scholar
[96]

Ilkaeva, M.; Krivtsov, I.; García-López, E. I.; Marcì, G.; Khainakova, O.; García, J. R.; Palmisano, L.; Díaz, E.; Ordóñez, S. Selective photocatalytic oxidation of 5-hydroxymethylfurfural to 2, 5- furandicarboxaldehyde by polymeric carbon nitride-hydrogen peroxide adduct. J. Catal. 2018, 359, 212-222.
DOI Google Scholar
[97]

Zhu, Y. K.; Zhang, Y.; Cheng, L. L.; Ismael, M.; Feng, Z. Y.; Wu, Y. Novel application of g-C3N4/NaNbO3 composite for photocatalytic selective oxidation of biomass-derived HMF to FFCA under visible light irradiation. Adv. Powder Technol. 2020, 31, 1148-1159.
DOI Google Scholar
[98]

Ayed, C.; Huang, W.; Kizilsavas, G.; Landfester, K.; Zhang, K. A. I. Photocatalytic partial oxidation of 5-hydroxymethylfurfural (HMF) to 2, 5-diformylfuran (DFF) over a covalent triazine framework in water. ChemPhotoChem 2020, 4, 571-576.
DOI Google Scholar
[99]

Zhang, M.; Li, Z.; Xin, X.; Zhang, J. H.; Feng, Y. Q.; Lv, H. J. Selective valorization of 5-hydroxymethylfurfural to 2, 5-diformylfuran using atmospheric O2 and MAPbBr3 perovskite under visible light. ACS Catal. 2020, 10, 14793-14800.
DOI Google Scholar
[100]

Wan, X. Y.; Zhou, C. M.; Chen, J. S.; Deng, W. P.; Zhang, Q. H.; Yang, Y. H.; Wang, Y. Base-free aerobic oxidation of 5-hydroxymethyl-furfural to 2, 5-furandicarboxylic acid in water catalyzed by functionalized carbon nanotube-supported Au-Pd alloy nanoparticles. ACS Catal. 2014, 4, 2175-2185.
DOI Google Scholar
[101]

Sharma, A. S.; Sharma, V. S.; Kaur, H.; Varma, R. S. Supported heterogeneous nanocatalysts in sustainable, selective and eco-friendly epoxidation of olefins. Green Chem. 2020, 22, 5902-5936.
DOI Google Scholar
[102]
BCC Research LLC. CHM102A Olefin Derivatives: Global Markets to 2022, 2018. https://www.bccresearch.com/market-research/chemicals/olefin-derivatives-global-markets.html (accessed April 11 2022)
[103]
Sienel, G.; Rieth, R.; Rowbottom, K. T. Epoxides. In Ullmann's Encyclopedia of Industrial Chemistry. Wiley-VCH Verlag GmbH & Co. KgaA: Weinheim, 2000.
[104]

Lin, M.; Xia, C. J.; Zhu, B.; Li, H.; Shu, X. T. Green and efficient epoxidation of propylene with hydrogen peroxide (HPPO process) catalyzed by hollow TS-1 zeolite: A 1.0 kt/a pilot-scale study. Chem. Eng. J. 2016, 295, 370-375.
DOI Google Scholar
[105]

Khatib, S. J.; Oyama, S. T. Direct oxidation of propylene to propylene oxide with molecular oxygen: A review. Catal. Rev. 2015, 57, 306-344.
DOI Google Scholar
[106]

Teržan, J.; Huš, M.; Likozar, B.; Djinović, P. Propylene epoxidation using molecular oxygen over copper- and silver-based catalysts: A review. ACS Catal. 2020, 10, 13415-13436.
DOI Google Scholar
[107]

Ohno, T.; Masaki, Y.; Hirayama, S.; Matsumura, M. TiO2- photocatalyzed epoxidation of 1-decene by H2O2 under visible light. J. Catal. 2001, 204, 163-168.
DOI Google Scholar
[108]

Huang, Y. M.; Liu, Z.; Gao, G. P.; Xiao, G.; Du, A. J.; Bottle, S.; Sarina, S.; Zhu, H. Y. Stable copper nanoparticle photocatalysts for selective epoxidation of alkenes with visible light. ACS Catal. 2017, 7, 4975-4985.
DOI Google Scholar
[109]

Marimuthu, A.; Zhang, J. W.; Linic, S. Tuning selectivity in propylene epoxidation by plasmon mediated photo-switching of Cu oxidation state. Science 2013, 339, 1590-1593.
DOI Google Scholar
[110]

Hosseini-Sarvari, M.; Bazyar, Z. Selective visible-light photocatalytic aerobic oxidation of alkenes to epoxides with Pd/ZnO nanoparticles. ChemistrySelect 2020, 5, 8853-8857.
DOI Google Scholar
[111]

Weerathunga, H.; Brock, A. J.; Sarina, S.; Deshan, A. D. K.; Zhu, H. Y.; Waclawik, E. R. AuCu/ZnO heterogeneous photocatalysts: Photodeposited AuCu alloy effect on product selectivity in alkene epoxidation. J. Photochem. Photobiol. A: Chem. 2022, 426, 113732.
DOI Google Scholar
[112]

Tan, H.; Kong, P.; Zhang, R. G.; Gao, M. T.; Liu, M. X.; Gu, X. M.; Liu, W. F.; Zheng, Z. F. Controllable generation of reactive oxygen species on cyano-group-modified carbon nitride for selective epoxidation of styrene. Innovation 2021, 2, 100089.
Google Scholar
[113]

Gu, Q.; Jiang, P. P.; Shen, Y. R.; Zhang, K.; Wai, P. T.; Haryono, A. Lamellar porous Mo-modified carbon nitride polymers photocatalytic epoxidation of olefins. Mol. Catal. 2021, 504, 111441.
DOI Google Scholar
[114]

Li, M.; Ma, L. N.; Luo, L.; Liu, Y. G.; Xu, M.; Zhou, H.; Wang, Y.; Li, Z. H.; Kong, X. G.; Duan, H. H. Efficient photocatalytic epoxidation of styrene over a quantum-sized SnO2 on carbon nitride as a heterostructured catalyst. Appl. Catal. B: Environ. 2022, 309, 121268.
DOI Google Scholar
[115]

Füldner, S.; Mild, R.; Siegmund, H. I.; Schroeder, J. A.; Gruber, M.; König, B. Green-light photocatalytic reduction using dye-sensitized TiO2 and transition metal nanoparticles. Green Chem. 2010, 12, 400-406.
DOI Google Scholar
[116]

Shiraishi, Y.; Togawa, Y.; Tsukamoto, D.; Tanaka, S.; Hirai, T. Highly efficient and selective hydrogenation of nitroaromatics on photoactivated rutile titanium dioxide. ACS Catal. 2012, 2, 2475-2481.
DOI Google Scholar
[117]

Liu, L. C.; Gu, X. R.; Ji, Z. Y.; Zou, W. X.; Tang, C. J.; Gao, F.; Dong, L. Anion-assisted synthesis of TiO2 nanocrystals with tunable crystal forms and crystal facets and their photocatalytic redox activities in organic reactions. J. Phys. Chem. C 2013, 117, 18578-18587.
DOI Google Scholar
[118]

Shiraishi, Y.; Hirakawa, H.; Togawa, Y.; Sugano, Y.; Ichikawa, S.; Hirai, T. Rutile crystallites isolated from degussa (Evonik) P25 TiO2: Highly efficient photocatalyst for chemoselective hydrogenation of nitroaromatics. ACS Catal. 2013, 3, 2318-2326.
DOI Google Scholar
[119]

Chen, Z.; Liu, S. Q.; Yang, M. Q.; Xu, Y. J. Synthesis of uniform CdS nanospheres/graphene hybrid nanocomposites and their application as visible light photocatalyst for selective reduction of nitro organics in water. ACS Appl. Mater. Interfaces 2013, 5, 4309-4319.
DOI Google Scholar
[120]

Eskandari, P.; Kazemi, F.; Zand, Z. Photocatalytic reduction of aromatic nitro compounds using CdS nanostructure under blue LED irradiation. J. Photochem. Photobiol. A: Chem. 2014, 274, 7-12.
DOI Google Scholar
[121]

Gao, W. Z.; Xu, Y.; Chen, Y.; Fu, W. F. Highly efficient and selective photocatalytic reduction of nitroarenes using the Ni2P/CdS catalyst under visible-light irradiation. Chem. Commun. 2015, 51, 13217-13220.
DOI Google Scholar
[122]

Toyao, T.; Saito, M.; Horiuchi, Y.; Mochizuki, K.; Iwata, M.; Higashimura, H.; Matsuoka, M. Efficient hydrogen production and photocatalytic reduction of nitrobenzene over a visible-light-responsive metal-organic framework photocatalyst. Catal. Sci. Technol. 2013, 3, 2092-2097.
DOI Google Scholar
[123]

Wu, W. M.; Lin, R.; Shen, L. J.; Liang, R. W.; Yuan, R. S.; Wu, L. Highly efficient visible-light-induced photocatalytic hydrogenation of nitrobenzene to aniline in water. RSC Adv. 2013, 3, 10894-10899.
DOI Google Scholar
[124]

Zhu, H. Y.; Ke, X. B.; Yang, X. Z.; Sarina, S.; Liu, H. W. Reduction of nitroaromatic compounds on supported gold nanoparticles by visible and ultraviolet light. Angew. Chem., Int. Ed. 2010, 49, 9657-9661.
DOI Google Scholar
[125]

Ke, X. B.; Zhang, X. G.; Zhao, J.; Sarina, S.; Barry, J.; Zhu, H. Y. Selective reductions using visible light photocatalysts of supported gold nanoparticles. Green Chem. 2013, 15, 236-244.
DOI Google Scholar
[126]

Naya, S. I.; Niwa, T.; Kume, T.; Tada, H. Visible-light-induced electron transport from small to large nanoparticles in bimodal gold nanoparticle-loaded titanium(IV) oxide. Angew. Chem., Int. Ed. 2014, 53, 7305-7309.
DOI Google Scholar
[127]

Mondal, B.; Mukherjee, P. S. Cage encapsulated gold nanoparticles as heterogeneous photocatalyst for facile and selective reduction of nitroarenes to Azo compounds. J. Am. Chem. Soc. 2018, 140, 12592-12601.
DOI Google Scholar
[128]

Xiao, Q.; Liu, Z.; Wang, F.; Sarina, S.; Zhu, H. Y. Tuning the reduction power of visible-light photocatalysts of gold nanoparticles for selective reduction of nitroaromatics to azoxy-compounds—Tailoring the catalyst support. Appl. Catal. B: Environ. 2017, 209, 69-79.
DOI Google Scholar
[129]

Liu, Z.; Huang, Y. M.; Xiao, Q.; Zhu, H. Y. Selective reduction of nitroaromatics to azoxy compounds on supported Ag-Cu alloy nanoparticles through visible light irradiation. Green Chem. 2016, 18, 817-825.
DOI Google Scholar
[130]
Zhang, D. S.; Ren, P. J.; Liu, W. W.; Li, Y. R.; Salli, S.; Han, F. Y.; Qiao, W.; Liu, Y.; Fan, Y. Z.; Cui, Y. et al. Photocatalytic abstraction of hydrogen atoms from water using hydroxylated graphitic carbon nitride for hydrogenative coupling reactions. Angew. Chem., Int. Ed., in press, https://doi.org/10.1002/anie.202204256.
[131]

Oger, C.; Balas, L.; Durand, T.; Galano, J. M. Are alkyne reductions chemo-, regio-, and stereoselective enough to provide pure (Z)-olefins in polyfunctionalized bioactive molecules?. Chem. Rev. 2013, 113, 1313-1350.
DOI Google Scholar
[132]

Feng, Q. C.; Zhao, S.; Wang, Y.; Dong, J. C.; Chen, W. X.; He, D. S.; Wang, D. S.; Yang, J.; Zhu, Y. M.; Zhu, H. L. et al. Isolated single-atom pd sites in intermetallic nanostructures: High catalytic selectivity for semihydrogenation of alkynes. J. Am. Chem. Soc. 2017, 139, 7294-7301.
DOI Google Scholar
[133]

Zhao, X. J.; Zhou, L. Y.; Zhang, W. Y.; Hu, C. Y.; Dai, L.; Ren, L. T.; Wu, B. H.; Fu, G.; Zheng, N. F. Thiol treatment creates selective palladium catalysts for semihydrogenation of internal alkynes. Chem 2018, 4, 1080-1091.
DOI Google Scholar
[134]

Wang, S.; Zhao, Z. J.; Chang, X.; Zhao, J. B.; Tian, H.; Yang, C. S.; Li, M. R.; Fu, Q.; Mu, R. T.; Gong, J. L. Activation and spillover of hydrogen on sub-1 nm palladium nanoclusters confined within sodalite zeolite for the semi-hydrogenation of alkynes. Angew. Chem., Int. Ed. 2019, 58, 7668-7672.
DOI Google Scholar
[135]

Kominami, H.; Higa, M.; Nojima, T.; Ito, T.; Nakanishi, K.; Hashimoto, K.; Imamura, K. Copper-modified titanium dioxide: A simple photocatalyst for the chemoselective and diastereoselective hydrogenation of alkynes to alkenes under additive-free conditions. ChemCatChem 2016, 8, 2019-2022.
DOI Google Scholar
[136]

Li, M. Q.; Zhang, N.; Long, R.; Ye, W.; Wang, C. M.; Xiong, Y. J. PdPt alloy nanocatalysts supported on TiO2: Maneuvering metal- hydrogen interactions for light-driven and water-donating selective alkyne semihydrogenation. Small 2017, 13, 1604173.
DOI Google Scholar
[137]

Kominami, H.; Shiba, M.; Hashimoto, A.; Imai, S.; Nakanishi, K.; Tanaka, A.; Hashimoto, K.; Imamura, K. Titanium(IV) oxide having a copper co-catalyst: A new type of semihydrogenation photocatalyst working efficiently at an elevated temperature under hydrogen-free and poison-free conditions. Phys. Chem. Chem. Phys. 2018, 20, 19321-19325.
DOI Google Scholar
[138]

Kojima, Y.; Fukui, M.; Tanaka, A.; Hashimoto, K.; Kominami, H. Additive-free semihydrogenation of an alkynyl group to an alkenyl group over Pd-TiO2 photocatalyst utilizing temporary in-situ deactivation. ChemCatChem 2018, 10, 3605-3611.
DOI Google Scholar
[139]

Fukui, M.; Omori, Y.; Kitagawa, S. Y.; Tanaka, A.; Hashimoto, K.; Kominami, H. Visible light-induced diastereoselective semihydrogenation of alkynes to cis-alkenes over an organically modified titanium(IV) oxide photocatalyst having a metal co- catalyst. J. Catal. 2019, 374, 36-42.
DOI Google Scholar
[140]

Lian, J. H.; Chai, Y. C.; Qi, Y.; Guo, X. Y.; Guan, N. J.; Li, L. D.; Zhang, F. X. Unexpectedly selective hydrogenation of phenylacetylene to styrene on titania supported platinum photocatalyst under 385 nm monochromatic light irradiation. Chin. J. Catal. 2020, 41, 598-603.
DOI Google Scholar
[141]

Su, K. Y.; Wang, Y. H.; Zhang, C. F.; Gao, Z. Y.; Han, J. Y.; Wang, F. Tuning the Pt species on Nb2O5 by support-induced modification in the photocatalytic transfer hydrogenation of phenylacetylene. Appl. Catal. B: Environ. 2021, 298, 120554.
DOI Google Scholar
[142]

Imai, S.; Kojima, Y.; Fudo, E.; Tanaka, A.; Kominami, H. Controlling the performance of a silver co-catalyst by a palladium core in TiO2-photocatalyzed alkyne semihydrogenation and H2 production. Appl. Catal. A: Gen. 2021, 624, 118331.
DOI Google Scholar
[143]

Jia, T. T.; Meng, D.; Ji, H. W.; Sheng, H.; Chen, C. C.; Song, W. J.; Zhao, J. C. Visible-light-driven semihydrogenation of alkynes via proton reduction over carbon nitride supported nickel. Appl. Catal. B: Environ. 2022, 304, 121004.
DOI Google Scholar
[144]

Luo, N. C.; Wang, M.; Li, H. J.; Zhang, J.; Hou, T. T.; Chen, H. J.; Zhang, X. C.; Lu, J. M.; Wang, F. Visible-light-driven self- hydrogen transfer hydrogenolysis of lignin models and extracts into phenolic products. ACS Catal. 2017, 7, 4571-4580.
DOI Google Scholar
[145]

Li, H. J.; Gao, Z. Y.; Lei, L. J.; Liu, H. F.; Han, J. Y.; Hong, F.; Luo, N. C.; Wang, F. Photocatalytic transfer hydrogenolysis of aromatic ketones using alcohols. Green Chem. 2020, 22, 3802-3808.
DOI Google Scholar
[146]

Shen, C. Q.; Ji, Y. J.; Wang, P. T.; Bai, S. X.; Wang, M.; Li, Y. Y.; Huang, X. Q.; Shao, Q. Interface confinement in metal nanosheet for high-efficiency semi-hydrogenation of alkynes. ACS Catal. 2021, 11, 5231-5239.
DOI Google Scholar
[147]

Sun, Z. H.; Fridrich, B.; de Santi, A.; Elangovan, S.; Barta, K. Bright side of lignin depolymerization: Toward new platform chemicals. Chem. Rev. 2018, 118, 614-678.
DOI Google Scholar
[148]

Liao, Y. H.; Koelewijn, S. F.; Van den Bossche, G.; Van Aelst, J.; Van den Bosch, S.; Renders, T.; Navare, K.; Nicolaï, T.; Van Aelst, K.; Maesen, M. et al. A sustainable wood biorefinery for low-carbon footprint chemicals production. Science 2020, 367, 1385-1390.
DOI Google Scholar
[149]

Wang, H. L.; Ruan, H.; Feng, M. Q.; Qin, Y. L.; Job, H.; Luo, L. L.; Wang, C. M.; Engelhard, M. H.; Kuhn, E.; Chen, X. W. et al. One-pot process for hydrodeoxygenation of lignin to alkanes using Ru-based bimetallic and bifunctional catalysts supported on Zeolite Y. ChemSusChem 2017, 10, 1846-1856.
DOI Google Scholar
[150]

Schutyser, W.; Kruger, J. S.; Robinson, A. M.; Katahira, R.; Brandner, D. G.; Cleveland, N. S.; Mittal, A.; Peterson, D. J.; Meilan, R.; Román-Leshkov, Y. et al. Revisiting alkaline aerobic lignin oxidation. Green Chem. 2018, 20, 3828-3844.
DOI Google Scholar
[151]

Wang, H. L.; Ruan, H.; Pei, H. S.; Wang, H. M.; Chen, X. W.; Tucker, M. P.; Cort, J. R.; Yang, B. Biomass-derived lignin to jet fuel range hydrocarbons via aqueous phase hydrodeoxygenation. Green Chem. 2015, 17, 5131-5135.
DOI Google Scholar
[152]

Schutyser, W.; Renders, T.; Van den Bosch, S.; Koelewijn, S. F.; Beckham, G. T.; Sels, B. F. Chemicals from lignin: An interplay of lignocellulose fractionation, depolymerisation, and upgrading. Chem. Soc. Rev. 2018, 47, 852-908.
DOI Google Scholar
[153]

Zhang, C. F.; Wang, F. Catalytic lignin depolymerization to aromatic chemicals. Acc. Chem. Res. 2020, 53, 470-484.
DOI Google Scholar
[154]

Xiang, Z. Y.; Han, W. Y.; Deng, J.; Zhu, W. B.; Zhang, Y.; Wang, H. J. Photocatalytic conversion of lignin into chemicals and fuels. ChemSusChem 2020, 13, 4199-4213.
DOI Google Scholar
[155]

Chen, H.; Wan, K.; Zheng, F. J.; Zhang, Z.; Zhang, Y. Y.; Long, D. H. Mechanism insight into photocatalytic conversion of lignin for valuable chemicals and fuels production: A state-of-the-art review. Renewable Sustainable Energy Rev. 2021, 147, 111217.
DOI Google Scholar
[156]

Lin, J. C.; Wu, X. J.; Xie, S. J.; Chen, L. Y.; Zhang, Q. H.; Deng, W. P.; Wang, Y. Visible-light-driven cleavage of C-O linkage for lignin valorization to functionalized aromatics. ChemSusChem 2019, 12, 5023-5031.
DOI Google Scholar
[157]

Wu, X. J.; Fan, X. T.; Xie, S. J.; Lin, J. C.; Cheng, J.; Zhang, Q. H.; Chen, L. Y.; Wang, Y. Solar energy-driven lignin-first approach to full utilization of lignocellulosic biomass under mild conditions. Nat. Catal. 2018, 1, 772-780.
DOI Google Scholar
[158]

Wu, X. J.; Xie, S. J.; Liu, C. X.; Zhou, C.; Lin, J. C.; Kang, J. C.; Zhang, Q. H.; Wang, Z. H.; Wang, Y. Ligand-controlled photocatalysis of CdS quantum dots for lignin valorization under visible light. ACS Catal. 2019, 9, 8443-8451.
DOI Google Scholar
[159]

Han, G. Q.; Yan, T.; Zhang, W.; Zhang, Y. C.; Lee, D. Y.; Cao, Z.; Sun, Y. J. Highly selective photocatalytic valorization of lignin model compounds using ultrathin metal/CdS. ACS Catal. 2019, 9, 11341-11349.
DOI Google Scholar
[160]

Yoo, H.; Lee, M. W.; Lee, S.; Lee, J.; Cho, S.; Lee, H.; Cha, H. G.; Kim, H. S. Enhancing photocatalytic β-O-4 bond cleavage in lignin model compounds by silver-exchanged cadmium sulfide. ACS Catal. 2020, 10, 8465-8475.
DOI Google Scholar
[161]

Li, P. F.; Ouyang, Y. X.; Xiao, G.; Zhao, Y. L.; Sarina, S.; Baeyens, J.; Su, H. J.; Zhu, H. Y. Non-plasmonic Ni nanoparticles catalyzed visible light selective hydrogenolysis of aryl ethers in lignin under mild conditions. Green Chem. 2021, 23, 7780-7789.
DOI Google Scholar
[162]

Liu, Z.; Huang, Y. M.; Xiao, G.; Li, P. F.; Su, H. J.; Sarina, S.; Zhu, H. Y. Visible-light-driven efficient cleavage of β-O-4 linkage in a lignin model compound: Phenethyl phenyl ether photocatalyzed by titanium nitride nanoparticles. Energy Fuels 2021, 35, 13315- 13324.
DOI Google Scholar
[163]
Ku, C. H.; Guo, H. Q.; Li, K. X.; Wu, Q.; Yan, L. S. One-step fabrication of mesoporous sulfur-doped carbon nitride for highly selective photocatalytic transformation of native lignin to monophenolic compounds. Chin. Chem. Lett., in press, https://doi.org/10.1016/j.cclet.2022.03.021.
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Received: 11 April 2022
Revised: 06 May 2022
Accepted: 10 May 2022
Published: 12 May 2022
Issue date: June 2022

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© The Author(s) 2022. Published by Tsinghua University Press.

Acknowledgements

Acknowledgements

This work was supported by the National Key R & D Program of China (No. 2020YFA0406103), the National Natural Science Foundation of China (NSFC) (Nos. 21725102 and 91961106), the Dalian National Laboratory for Clean Energy (DNL) Cooperation Fund, Chinese Academy of Sciences (CAS) (No. DNL201922), and the startup grant from University of Science and Technology of China (USTC) (No. KY2260080010).

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