Abstract
Hydrogen transfer reaction is one of the valuable and potential solutions for selective hydrogenation. We report here that single-atom Pt supported by CeO2 could effectively catalyze the selective hydrogenation of nitroaromatics to corresponding amine through hydrogen transfer reaction.
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Hao CH, Guo X, Pan YT, Chen S, Jiao Z, Yang H, Guo XY (2016) Visible-light-driven selective photocatalytic hydrogenation of cinnamaldehyde over Au/SiC catalysts. J Am Chem Soc 138(30):9361
Roeder GJ, Kelly HR, Yang G, Bauer TJ, Baráth E (2021) Selective Heterogeneous transfer hydrogenation from tertiary amines to alkynes. ACS Catal 11(9):5405–5415
Zhang L, Zhou M, Wang A, Zhang T (2019) Selective hydrogenation over supported metal catalysts: from nanoparticles to single atoms. Chem Rev 120(2):683
Zhang Y, Gyngazova MS, Lolli A, Grazia L, Tabanelli T, Cavani F, Albonetti S (2019) Hydrogen transfer reaction as an alternative reductive process for the valorization of biomass-derived building blocks. Stud Surf Sci Catal 178:195–214
Xu M, Yao S, Rao D, Niu Y, Liu N, Peng M, Zhai P, Man Y, Zheng L, Wang B (2018) Insights into interfacial synergistic catalysis over Ni@TiO2-x catalyst toward water-gas shift reaction. J Am Chem Soc 140(36):11241–11251
Li T, Chen F, Lang R, Wang H, Su Y, Qiao B, Wang A, Zhang T (2020) Styrene hydroformylation with in situ hydrogen: regioselectivity control by coupling with the low-temperature water–gas shift reaction. Angew Chem 132(19):7430
Shang Q, Tang N, Qi H, Chen S, Cong Y (2020) A palladium single-atom catalyst toward efficient activation of molecular oxygen for cinnamyl alcohol oxidation. Chin J Catal 41(12):1812–1817
Mza C, Man Y, Xy A, Xz A, Lei SD, Wd D, Awa B, Jl E, Tao Z (2020) On the mechanism of H2 activation over single-atom catalyst: an understanding of Pt1/WOx in the hydrogenolysis reaction. Chin J Catal 41(3):524–532
Wang W, Lin L, Qi H, Cao W, Luo W (2021) MIL-53 (Al) derived single-atom Rh catalyst for the selective hydrogenation of m-chloronitrobenzene into m-chloroaniline. Chin J Catal 42(5):824–834
Qu J, Xiao J, Chen H, Liu X, Zhang Q (2021) Orbital symmetry matching: achieving superior nitrogen reduction reaction over single-atom catalysts anchored on Mxene substrates. Chin J Catal 42(2):288–296
Aitbekova A, Wrasman CJ, Riscoe AR, Kunz LY, Cargnello M (2020) Determining number of sites on ceria stabilizing single atoms via metal nanoparticle redispersion. Chin J Catal 41(6):998–1005
Zhou D, Zhang L, Liu W, Xu G, Yin J (2021) Reaction kinetics and phase behavior in the chemoselective hydrogenation of 3-nitrostyrene over Co-N-C single-atom catalyst in compressed CO2. Chin J Catal 42(9):1617–1624
Zhu C, Liang JX, Meng Y, Lin J, Cao Z (2021) Mn-corrolazine-based 2D-nanocatalytic material with single Mn atoms for catalytic oxidation of alkane to alcohol. Chin J Catal 42(6):1030–1039
Jiang JS, Wei HL, Tan AD, Si R, Yu YX (2021) Fabricating high-loading Fe-N4 single-atom catalysts for oxygen reduction reaction by carbon-assisted pyrolysis of metal complexes. Chin J Catal 42(5):753–761
Zhou X (2021) TiO2-supported single-atom catalysts for photocatalytic reactions. Acta Physico-Chim Sin 37(6):2008064
Han B (2021) Single NiN3 atoms for efficient electrochemical reduction of CO2. Acta Physico-Chim Sin 37(7):2010068
Dong F (2021) High-performance single-atom implanted metal-organic framework/MNO2 for NOx oxidation in plasma. Acta Phys-Chim Sin 37(8):2010074
Zhou J, Ao Z, An T (2021) DFT study of the decomposition mechanism of H2S on V-decorated Ti2CO2 single-atom catalyst. Acta Physico-Chim Sin 37(8):2007086
Huang X, Ma Y, Zhi L (2022) Ultrathin nitrogenated carbon nanosheets with single-atom nickel as an efficient catalyst for electrochemical CO2 reduction. Acta Physico-Chim Sin 38(2):211050
Zhang X, Zhang M, Deng Y, Xu M, Ma D (2021) A stable low-temperature H2-production catalyst by crowding Pt on α-MoC. Nature 589(7842):396–401
Peng M, Dong C, Gao R, Xiao D, Liu H, Ma D (2021) Fully exposed cluster catalyst (FECC): toward rich surface sites and full atom utilization efficiency. ACS Cent Sci 7(2):262–273
Han B, Guo Y, Huang Y, Xi W, Xu J, Luo J, Qi H, Ren Y, Liu X, Qiao B (2020) Strong metal–support interactions between Pt single atoms and TiO2. Angew Chem Int Ed 59(29):11824
Pei GX, Liu XY, Yang X, Zhang L, Wang A, Li L, Wang H, Wang X, Zhang T (2017) Performance of Cu-alloyed Pd single-atom catalyst for semihydrogenation of acetylene under simulated front-end conditions. ACS Catal 7(2):1491–1500
Zhang Z, Zhu Y, Asakura H, Zhang B, Zhang J, Zhou M, Han Y, Tanaka T, Wang A, Zhang T (2017) Thermally stable single atom Pt/m-Al2O3 for selective hydrogenation and CO oxidation. Nat Commun 8:16100
Huang F, Deng Y, Chen Y, Cai X, Peng M, Jia Z, Ren P, Xiao D, Wen X, Wang N (2018) Atomically dispersed Pd on nanodiamond/graphene hybrid for selective hydrogenation of acetylene. J Am Chem Soc 140(41):13142–13146
Liu Z, Huang F, Peng M, Chen Y, Cai X, Wang L, Hu Z, Wen X, Wang N, Xiao D, Jiang H, Sun H, Liu H, Ma D (2021) Tuning the selectivity of catalytic nitriles hydrogenation by structure regulation in atomically dispersed Pd catalysts. Nat Commun 12:6194
Liu L, Corma A (2018) Metal catalysts for heterogeneous catalysis: from single atoms to nanoclusters and nanoparticles. Chem Rev 2018:4981–5079
Li T, Liu F, Tang Y, Li L, Miao S, Su Y, Zhang J, Huang J, Sun H, Haruta M (2018) Maximizing the number of interfacial sites in single-atom catalysts for the highly selective, solvent-free oxidation of primary alcohols. Angew Chem Int Ed 57(26):7795–7799
Tang Y, Asokan C, Xu MJ, Graham GW, Pan XQ, Christopher P, Li J, Sautet P (2019) Rh single atoms on TiO2 dynamically respond to reaction conditions by adapting their site. Nat Commun 10:4488
Beswick O, Parastaev A, Yuranov I, LaGrange T, Dyson PJ, Kiwi-Minsker L (2017) Highly dispersed cobalt oxides nanoparticles on activated carbon fibres as efficient structured catalysts for the transfer hydrogenation of m-nitrostyrene. Catal Today 279:29–35
Wang J, Yuan Z, Nie R, Hou Z, Zheng X (2010) Hydrogenation of nitrobenzene to aniline over silica gel supported nickel catalysts. Ind Eng Chem Res 49(10):4664–4669
Fujita S-I, Watanabe H, Katagiri A, Yoshida H, Arai M (2014) Nitrogen and oxygen-doped metal-free carbon catalysts for chemoselective transfer hydrogenation of nitrobenzene, styrene, and 3-nitrostyrene with hydrazine. J Mol Catal A Chem 393:257–262
Wei H, Liu X, Wang A, Zhang L, Qiao B, Yang X, Huang Y, Miao S, Liu J, Zhang T (2014) FeOx-supported platinum single-atom and pseudo-single-atom catalysts for chemoselective hydrogenation of functionalized nitroarenes. Nat Commun 5:5634
Serna P, Boronat M, Corma A (2011) Tuning the behavior of Au and Pt catalysts for the chemoselective hydrogenation of nitroaromatic compounds. Top Catal 54(5):439–446
Ding GD, Hao LD, Xu HP, Wang LG, Chen J, Li T, Tu XM, Zhang Q (2020) Atomically dispersed palladium catalyses Suzuki-Miyaura reactions under phosphine-free conditions. Commun Chem 3(1):8
Fujiwara K, Pratsinis SE (2018) Single Pd atoms on TiO2 dominate photocatalytic NOx removal. Appl Catal B-Environ 226:127–134
Lu ZS, Lv P, Xue J, Wang HH, Wang YZ, Huang Y, He CZ, Mac DW, Yang ZX (2015) Pd-1/BN as a promising single atom catalyst of CO oxidation: a dispersion-corrected density functional theory study. RSC Adv 5(103):84381–84388
Qiao BT, Liang JX, Wang AQ, Xu CQ, Li J, Zhang T, Liu JY (2015) Ultrastable single-atom gold catalysts with strong covalent metal-support interaction (CMSI). Nano Res 8(9):2913–2924
Wang BL, Yue YX, Jin CX, Lu JY, Wang SS, Yu L, Guo LL, Li RR, Hu ZT, Pan ZY, Zhao J, Li XN (2020) Hydrochlorination of acetylene on single-atom Pd/N-doped carbon catalysts: Importance of pyridinic-N synergism. Appl Catal B-Environ 272:11
Lang R, Xi W, Liu JC, Cui YT, Li T, Lee AF, Chen F, Chen Y, Li L, Li L (2019) Non defect-stabilized thermally stable single-atom catalyst. Nat Commun 10:234
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This work was supported by the National Natural Science Foundation of China (22102210).
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Li, T., Jian, X., Jiang, Q. et al. Selective Hydrogenation of Nitroarenes by Single-Atom Pt Catalyst Through Hydrogen Transfer Reaction. Top Catal 65, 1604–1608 (2022). https://doi.org/10.1007/s11244-022-01566-w
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DOI: https://doi.org/10.1007/s11244-022-01566-w