Recent progress in electrochemical C–N coupling reactions
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Bariwal, 2013, C–N bond forming cross-coupling reactions: an overview, Chem. Soc. Rev., 42, 9283, 10.1039/c3cs60228a
Wang, 2019, Organonitrogen chemicals from oxygen-containing feedstock over heterogeneous catalysts, ACS Catal., 10, 311, 10.1021/acscatal.9b03744
Lv, 2020, Direct transformation of dinitrogen: synthesis of N-containing organic compounds via N−C bond formation, Natl. Sci. Rev., 7, 1564, 10.1093/nsr/nwaa142
Corbin, 1997, Methylamines synthesis: a review, Catal. Today, 37, 71, 10.1016/S0920-5861(97)00003-5
Lanigan, 2013, Recent developments in amide synthesis: direct amidation of carboxylic acids and transamidation reactions, Eur. J. Org. Chem., 2013, 7453, 10.1002/ejoc.201300573
Pérez-Fortes, 2014, CO2 utilization pathways: techno-economic assessment and market opportunities, Energy Proc., 63, 7968, 10.1016/j.egypro.2014.11.834
Erisman, 2008, How a century of ammonia synthesis changed the world, Nat. Geosci., 1, 636, 10.1038/ngeo325
Kim, 2020, Electrochemical C–N bond formation for sustainable amine synthesis, Trends. Chem., 2, 1004, 10.1016/j.trechm.2020.09.003
Zhang, 2018, Refining defect states in W18O49 by Mo doping: a strategy for tuning N2 activation towards solar-driven nitrogen fixation, J. Am. Chem. Soc., 140, 9434, 10.1021/jacs.8b02076
Yang, 2018, Atomically dispersed Ni(Ⅰ) as the active site for electrochemical CO2 reduction, Nat. Energy, 3, 140, 10.1038/s41560-017-0078-8
Tao, 2021, Accessing organonitrogen compounds via C–N coupling in electrocatalytic CO2 reduction, J. Am. Chem. Soc., 143, 19630, 10.1021/jacs.1c10714
Nitopi, 2019, Progress and perspectives of electrochemical CO2 reduction on copper in aqueous electrolyte, Chem. Rev., 119, 7610, 10.1021/acs.chemrev.8b00705
Chen, 2020, Coupling N2 and CO2 in H2O to synthesize urea under ambient conditions, Nat. Chem., 12, 717, 10.1038/s41557-020-0481-9
Zheng, 2019, Understanding the roadmap for electrochemical reduction of CO2 to multi-carbon oxygenates and hydrocarbons on copper-based catalysts, J. Am. Chem. Soc., 141, 7646, 10.1021/jacs.9b02124
Wang, 2021, Electrocatalysis for CO2 conversion: from fundamentals to value-added products, Chem. Soc. Rev., 50, 4993, 10.1039/D0CS00071J
Zhong, 2022, In situ resource utilization of lunar soil for highly efficient extraterrestrial fuel and oxygen supply, Natl. Sci. Rev.
Xu, 2022, Electrocatalytic reduction of nitrate — a step towards a sustainable nitrogen cycle, Chem. Soc. Rev., 51, 2710, 10.1039/D1CS00857A
Wang, 2021, Nitrate electroreduction: mechanism insight, in situ characterization, performance evaluation, and challenges, Chem. Soc. Rev., 50, 6720, 10.1039/D1CS00116G
Yang, 2021, Recent progress in electrochemical synthesis of ammonia from nitrogen: strategies to improve the catalytic activity and selectivity, Energy Environ. Sci., 14, 672, 10.1039/D0EE02263B
Qing, 2020, Recent advances and challenges of electrocatalytic N2 reduction to ammonia, Chem. Rev., 120, 5437, 10.1021/acs.chemrev.9b00659
Li, 2022, Construction of C–N bonds from small-molecule precursors through heterogeneous electrocatalysis, Nat. Rev. Chem, 6, 303, 10.1038/s41570-022-00379-5
Huang, 2021, Electrocatalytic construction of the C–N bond from the derivates of CO2 and N2, Sci. China Chem., 65, 204, 10.1007/s11426-021-1173-8
Zhang, 2020, Metal-free electrocatalysts for nitrogen reduction reaction, Energy, 2
Kayan, 2016, Simultaneous electrocatalytic reduction of dinitrogen and carbon dioxide on conducting polymer electrodes, Appl. Catal. B, 181, 88, 10.1016/j.apcatb.2015.07.045
Yuan, 2021, Electrochemical C–N coupling with perovskite hybrids toward efficient urea synthesis, Chem. Sci., 12, 6048, 10.1039/D1SC01467F
Yuan, 2021, Unveiling electrochemical urea synthesis by co-activation of CO2 and N2 with Mott-Schottky heterostructure catalysts, Angew. Chem. Int. Ed., 60, 11005, 10.1002/ange.202101275
Yuan, 2022, Artificial frustrated Lewis pairs facilitating the electrochemical N2 and CO2 conversion to urea, Chem Catal., 2, 309, 10.1016/j.checat.2021.11.009
Yuan, 2021, Highly selective electroreduction of N2 and CO2 to urea over artificial frustrated Lewis pairs, Energy Environ. Sci., 14, 6605, 10.1039/D1EE02485J
Yuan, 2022, Host–guest molecular interaction promoted urea electrosynthesis over a precisely designed conductive metal–organic framework, Energy Environ. Sci., 15, 2084, 10.1039/D1EE03918K
Medford, 2015, From the Sabatier principle to a predictive theory of transition-metal heterogeneous catalysis, J. Catal., 328, 36, 10.1016/j.jcat.2014.12.033
Tang, 2021, Electrocatalytic refinery for sustainable production of fuels and chemicals, Angew. Chem. Int. Ed., 60, 2, 10.1002/anie.202101522
He, 2018, Electrocatalytic alloys for CO2 reduction, ChemSusChem, 11, 48, 10.1002/cssc.201701825
Mistry, 2016, Nanostructured electrocatalysts with tunable activity and selectivity, Nat. Rev. Mater., 1, 10.1038/natrevmats.2016.9
Tang, 2012, The importance of surface morphology in controlling the selectivity of polycrystalline copper for CO2 electroreduction, Phys. Chem. Chem. Phys., 14, 76, 10.1039/C1CP22700A
Chen, 2020, Active site engineering in porous electrocatalysts, Adv. Mater., 32
Wang, 2019, Defect engineering in earth-abundant electrocatalysts for CO2 and N2 reduction, Energy Environ. Sci., 12, 1730, 10.1039/C8EE03781G
Wang, 2018, Defect and interface engineering for aqueous electrocatalytic CO2 reduction, Joule, 2, 2551, 10.1016/j.joule.2018.09.021
Vasileff, 2018, Surface and interface engineering in copper-based bimetallic materials for selective CO2 electroreduction, Chem, 4, 1809, 10.1016/j.chempr.2018.05.001
Shchukin, 2005, Urea photosynthesis inside polyelectrolyte capsules: effect of confined media, Langmuir, 21, 5582, 10.1021/la050429+
Yang, 2020, Protecting copper oxidation state via intermediate confinement for selective CO2 electroreduction to C2+ fuels, J. Am. Chem. Soc., 142, 6400, 10.1021/jacs.0c01699
Liang, 2022, Recent advances in nanostructured heterogeneous catalysts for N-cycle electrocatalysis, Nano Res. Energy, 1, 10.26599/NRE.2022.9120010
Zeng, 2020, Restoring the nitrogen cycle by electrochemical reduction of nitrate: progress and prospects, Small Methods
Hao, 2021, Emerging artificial nitrogen cycle processes through novel electrochemical and photochemical synthesis, Mater. Today, 46, 212, 10.1016/j.mattod.2021.01.029
Li, 2022, ITO@TiO2 nanoarray: an efficient and robust nitrite reduction reaction electrocatalyst toward NH3 production under ambient conditions, eScience, 2, 382, 10.1016/j.esci.2022.04.008
Fan, 2021, In situ grown Fe3O4 particle on stainless steel: a highly efficient electrocatalyst for nitrate reduction to ammonia, Nano Res., 15, 3050, 10.1007/s12274-021-3951-5
Shibata, 1995, Electrochemical synthesis of urea on reduction of carbon dioxide with nitrate and nitrite ions using Cu-loaded gas-diffusion electrode, J. Electroanal. Chem., 387, 143, 10.1016/0022-0728(95)03992-P
Shibata, 1998, Electrochemical synthesis of urea at gas-diffusion electrodes V. simultaneous reduction of carbon dioxide and nitrite ions with various boride catalysts, J. Electroanal. Chem., 66, 584
Shibata, 1998, Electrochemical synthesis of urea at gas-diffusion electrodes: III. simultaneous reduction of carbon dioxide and nitrite ions with various metal catalysts, J. Electrochem. Soc., 145, 595, 10.1149/1.1838309
Shibata, 1998, Electrochemical synthesis of urea at gas-diffusion electrodes: part II. simultaneous reduction of carbon dioxide and nitrite ions at Cu, Ag and Au catalysts, J. Electroanal. Chem., 442, 67, 10.1016/S0022-0728(97)00504-4
Shibata, 1998, Electrochemical synthesis of urea at gas-diffusion electrodes: IV. simultaneous reduction of carbon dioxide and nitrate ions with various metal catalysts, J. Electrochem. Soc., 145, 2348, 10.1149/1.1838641
Liu, 2022, AuCu nanofibers for electrosynthesis of urea from carbon dioxide and nitrite, Cell Rep. Phys. Sci., 3
Meng, 2022, Oxide-derived core-shell Cu@Zn nanowires for urea electrosynthesis from carbon dioxide and nitrate in water, ACS Nano, 16, 9095, 10.1021/acsnano.2c01177
Feng, 2020, Te-Doped Pd nanocrystal for electrochemical urea production by efficiently coupling carbon dioxide reduction with nitrite reduction, Nano Lett., 20, 8282, 10.1021/acs.nanolett.0c03400
Shibata, 2001, Electrochemical synthesis of urea at gas-diffusion electrodes: part VI. Simultaneous reduction of carbon dioxide and nitrite ions with various metallophthalocyanine catalysts, J. Electroanal. Chem., 507, 177, 10.1016/S0022-0728(01)00363-1
Siva, 2017, Electrocatalytic conversion of carbon dioxide to urea on nano-FeTiO3 surface, Ionics, 23, 1871, 10.1007/s11581-017-1985-1
Saravanakumar, 2017, Electrocatalytic conversion of carbon dioxide and nitrate ions to urea by a titania-nafion composite electrode, ChemSusChem, 10, 3999, 10.1002/cssc.201701448
Cao, 2020, Oxygen vacancies enhanced cooperative electrocatalytic reduction of carbon dioxide and nitrite ions to urea, J. Colloid Interface Sci., 577, 109, 10.1016/j.jcis.2020.05.014
Liu, 2022, Carbon nanotubes with fluorine-rich surface as metal-free electrocatalyst for effective synthesis of urea from nitrate and CO2, Appl. Catal. B, 316, 10.1016/j.apcatb.2022.121618
Wei, 2022, Oxygen vacancy-mediated selective C–N coupling toward electrocatalytic urea synthesis, J. Am. Chem. Soc., 144, 11530, 10.1021/jacs.2c03452
Meng, 2021, Electrosynthesis of urea from nitrite and CO2 over oxygen vacancy-rich ZnO porous nanosheets, Cell Rep. Phys. Sci., 2
Tada, 2005, Kinetic studies of reduction of nitrate ions at Sn-modified Pt electrodes using a quartz crystal microbalance, J. Electroanal. Chem., 577, 303, 10.1016/j.jelechem.2004.11.039
Rosca, 2009, Nitrogen cycle electrocatalysis, Chem. Rev., 109, 2209, 10.1021/cr8003696
Guo, 2017, Insights into nitrate reduction over Indium-decorated palladium nanoparticle catalysts, ACS Catal., 8, 503, 10.1021/acscatal.7b01371
Camargo, 2006, Ecological and toxicological effects of inorganic nitrogen pollution in aquatic ecosystems: a global assessment, Environ. Int., 32, 831, 10.1016/j.envint.2006.05.002
Lv, 2021, Selective electrocatalytic synthesis of urea with nitrate and carbon dioxide, Nat. Sustain., 4, 868, 10.1038/s41893-021-00741-3
Wu, 2021, Direct electrosynthesis of methylamine from carbon dioxide and nitrate, Nat. Sustain., 4, 725, 10.1038/s41893-021-00705-7
Tao, 2022, Cascade electrocatalytic reduction of carbon dioxide and nitrate to ethylamine, J. Energy Chem., 65, 367, 10.1016/j.jechem.2021.06.007
Kim, 2021, Electrochemical synthesis of glycine from oxalic acid and nitrate, Angew. Chem. Int. Ed., 60, 21943, 10.1002/anie.202108352
Sigurdarson, 2018, The molecular processes of urea hydrolysis in relation to ammonia emissions from agriculture, Rev. Environ. Sci. Biotechnol., 17, 241, 10.1007/s11157-018-9466-1
Mani, 2006, CO2 absorption by aqueous NH3 solutions: speciation of ammonium carbamate, bicarbonate and carbonate by a 13C NMR study, Green Chem., 8, 995, 10.1039/b602051h
Jouny, 2019, Formation of carbon-nitrogen bonds in carbon monoxide electrolysis, Nat. Chem., 11, 846, 10.1038/s41557-019-0312-z
Jouny, 2019, Carbon monoxide electroreduction as an emerging platform for carbon utilization, Nat. Catal., 2, 1062, 10.1038/s41929-019-0388-2
Li, 2022, Electrochemically driven C–N bond formation from CO2 and ammonia at the triple-phase boundary, Chem. Sci., 13, 3957, 10.1039/D1SC06590D
Chen, 2021, Electrocatalytic C–N coupling for urea synthesis, Small Science, 1, 10.1002/smsc.202100070
Zhu, 2021, Electrochemical synthesis of urea on MBenes, Nat. Commun., 12, 4080, 10.1038/s41467-021-24400-5
Fu, 2021, Dual-sites tandem catalysts for C–N bond formation via electrocatalytic coupling of CO2 and nitrogenous small molecules, ACS Materials Lett., 3, 1468, 10.1021/acsmaterialslett.1c00375
Yao, 2018, Carbothermal shock synthesis of high-entropy-alloy nanoparticles, Science, 359, 1489, 10.1126/science.aan5412
Zhu, 2022, Establishing the principal descriptor for electrochemical urea production via the dispersed dual-metals anchored on the N-decorated graphene, Adv. Sci., 9, 10.1002/advs.202105697
Fan, 2020, Strategies in catalysts and electrolyzer design for electrochemical CO2 reduction toward C2+ products, Sci. Adv., 6, 10.1126/sciadv.aay3111
Rabiee, 2021, Gas diffusion electrodes (GDEs) for electrochemical reduction of carbon dioxide, carbon monoxide, and dinitrogen to value-added products: a review, Energy Environ. Sci., 14, 1959, 10.1039/D0EE03756G
Yang, 2021, Reactor design for electrochemical CO2 conversion toward large-scale applications, Curr. Opin. Green Sustain. Chem., 27
Battino, 1984, The solubility of nitrogen and air in liquids, J. Phys. Chem. Ref. Data, 13, 563, 10.1063/1.555713
Sun, 2017, Fundamentals and challenges of electrochemical CO2 reduction using two-dimensional materials, Chem, 3, 560, 10.1016/j.chempr.2017.09.009
Liang, 2020, Electrolytic cell design for electrochemical CO2 reduction, J. CO2 Util., 35, 90, 10.1016/j.jcou.2019.09.007
Lv, 2018, A highly porous copper electrocatalyst for carbon dioxide reduction, Adv. Mater., 30, 10.1002/adma.201803111
Nguyen, 2020, Gas diffusion electrode design for electrochemical carbon dioxide reduction, Chem. Soc. Rev., 49, 7488, 10.1039/D0CS00230E
Dinh, 2018, CO2 electroreduction to ethylene via hydroxide-mediated copper catalysis at an abrupt interface, Science, 360, 783, 10.1126/science.aas9100
Huang, 2021, CO2 electrolysis to multicarbon products in strong acid, Science, 372, 1074, 10.1126/science.abg6582
Jouny, 2018, High-rate electroreduction of carbon monoxide to multi-carbon products, Nat. Catal., 1, 748, 10.1038/s41929-018-0133-2
Jouny, 2018, General techno-economic analysis of CO2 electrolysis systems, Ind. Eng. Chem. Res., 57, 2165, 10.1021/acs.iecr.7b03514
Ma, 2020, Electrocatalytic reduction of CO2 to ethylene and ethanol through hydrogen-assisted C–C coupling over fluorine-modified copper, Nat. Catal., 3, 478, 10.1038/s41929-020-0450-0
Gu, 2021, Efficient electrocatalytic CO2 reduction to C2+ alcohols at defect-site-rich Cu surface, Joule, 5, 429, 10.1016/j.joule.2020.12.011
Li, 2021, Stable, active CO2 reduction to formate via redox-modulated stabilization of active sites, Nat. Commun., 12, 5223, 10.1038/s41467-021-25573-9
Li, 2019, Molecular tuning of CO2-to-ethylene conversion, Nature, 577, 509, 10.1038/s41586-019-1782-2
He, 2021, Cu2−xS derived copper nanoparticles: a platform for unraveling the role of surface reconstruction in efficient electrocatalytic CO2-to-C2H4 conversion, Nano Res., 10.1007/s12274-021-3532-7
Jiang, 2022, Structural reconstruction of Cu2O superparticles toward electrocatalytic CO2 reduction with high C2+ products selectivity, Adv. Sci., 9, 10.1002/advs.202105292
Zhang, 2022, Identifying and tailoring C–N coupling site for efficient urea synthesis over diatomic Fe-Ni catalyst, Nat. Commun., 13, 5337, 10.1038/s41467-022-33066-6
Zhao, 2021, Simultaneous oxidative and reductive reactions in one system by atomic design, Nat. Catal., 4, 134, 10.1038/s41929-020-00563-0
Xia, 2019, Continuous production of pure liquid fuel solutions via electrocatalytic CO2 reduction using solid-electrolyte devices, Nat. Energy, 4, 776, 10.1038/s41560-019-0451-x
Tan, 2021, Ionic liquid-based electrolytes for CO2 electroreduction and CO2 electroorganic transformation, Natl. Sci. Rev., 9