{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,6,11]],"date-time":"2026-06-11T05:00:04Z","timestamp":1781154004314,"version":"3.54.1"},"reference-count":73,"publisher":"Frontiers Media SA","license":[{"start":{"date-parts":[[2021,11,24]],"date-time":"2021-11-24T00:00:00Z","timestamp":1637712000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/100007479","name":"Fondazione Cassa di Risparmio di Padova e Rovigo","doi-asserted-by":"publisher","id":[{"id":"10.13039\/100007479","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003500","name":"Universit\u00e0 Degli Studi di Padova","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100003500","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":["frontiersin.org"],"crossmark-restriction":true},"short-container-title":["Front. Chem."],"abstract":"<jats:p>The utilization of carbon dioxide as a raw material represents nowadays an appealing strategy in the renewable energy, organic synthesis, and green chemistry fields. Besides reduction strategies, carbon dioxide can be exploited as a single-carbon-atom building block through its fixation into organic scaffolds with the formation of new C-C bonds (carboxylation processes). In this case, activation of the organic substrate is commonly required, upon formation of a carbanion C<jats:sup>\u2212<\/jats:sup>, being sufficiently reactive toward the addition of CO<jats:sub>2<\/jats:sub>. However, the prediction of the reactivity of C<jats:sup>\u2212<\/jats:sup> with CO<jats:sub>2<\/jats:sub> is often problematic with the process being possibly associated with unfavorable thermodynamics. In this contribution, we present a thermodynamic analysis combined with density functional theory calculations on 50 organic molecules enabling the achievement of a linear correlation of the standard free energy (\u0394G<jats:sup>0<\/jats:sup>) of the carboxylation reaction with the basicity of the carbanion C<jats:sup>\u2212<\/jats:sup>, expressed as the pK<jats:sub>a<\/jats:sub> of the CH\/C<jats:sup>\u2212<\/jats:sup> couple. The analysis identifies a threshold pK<jats:sub>a<\/jats:sub> of ca 36 (in CH<jats:sub>3<\/jats:sub>CN) for the CH\/C<jats:sup>\u2212<\/jats:sup> couple, above which the \u0394G<jats:sup>0<\/jats:sup> of the carboxylation reaction is negative and indicative of a favorable process. We then apply the model to a real case involving electrochemical carboxylation of flavone and chalcone as model compounds of \u03b1,\u03b2-unsaturated ketones. Carboxylation occurs in the \u03b2-position from the doubly reduced dianion intermediates of flavone and chalcone (calculated \u0394G<jats:sup>0<\/jats:sup> of carboxylation in \u03b2 = \u221212.8 and \u221220.0 Kcalmol<jats:sup>-1<\/jats:sup> for flavone and chalcone, respectively, associated with pK<jats:sub>a<\/jats:sub> values for the conjugate acids of 50.6 and 51.8, respectively). Conversely, the one-electron reduced radical anions are not reactive toward carboxylation (\u0394G<jats:sup>0<\/jats:sup> &amp;gt; +20 Kcalmol<jats:sup>-1<\/jats:sup> for both substrates, in either \u03b1 or \u03b2 position, consistent with pK<jats:sub>a<\/jats:sub> of the conjugate acids &amp;lt; 18.5). For all the possible intermediates, the plot of calculated \u0394G<jats:sup>0<\/jats:sup> of carboxylation vs. pK<jats:sub>a<\/jats:sub> is consistent with the linear correlation model developed. The application of the \u0394G<jats:sup>0<\/jats:sup> vs. pK<jats:sub>a<\/jats:sub> correlation is finally discussed for alternative reaction mechanisms and for carboxylation of other C=C and C=O double bonds. These results offer a new mechanistic tool for the interpretation of the reactivity of CO<jats:sub>2<\/jats:sub> with organic intermediates.<\/jats:p>","DOI":"10.3389\/fchem.2021.783993","type":"journal-article","created":{"date-parts":[[2021,11,30]],"date-time":"2021-11-30T22:55:08Z","timestamp":1638312908000},"update-policy":"https:\/\/doi.org\/10.3389\/crossmark-policy","source":"Crossref","is-referenced-by-count":9,"title":["Basicity as a Thermodynamic Descriptor of Carbanions Reactivity with Carbon Dioxide: Application to the Carboxylation of \u03b1,\u03b2-Unsaturated Ketones"],"prefix":"10.3389","volume":"9","author":[{"given":"Pietro","family":"Franceschi","sequence":"first","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Catia","family":"Nicoletti","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Ruggero","family":"Bonetto","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Marcella","family":"Bonchio","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mirco","family":"Natali","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Luca","family":"Dell\u2019Amico","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Andrea","family":"Sartorel","sequence":"additional","affiliation":[],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1965","published-online":{"date-parts":[[2021,11,24]]},"reference":[{"key":"B1","doi-asserted-by":"publisher","first-page":"5734","DOI":"10.1021\/acscatal.0c00478","article-title":"Photocatalytic CO2 Reduction to C2+ Products","volume":"10","author":"Albero","year":"2020","journal-title":"ACS Catal."},{"key":"B2","doi-asserted-by":"publisher","first-page":"1780","DOI":"10.1021\/jacs.9b13305","article-title":"Harnessing Applied Potential: Selective \u03b2-Hydrocarboxylation of Substituted Olefins","volume":"142","author":"Alkayal","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"B3","doi-asserted-by":"publisher","first-page":"16639","DOI":"10.1021\/jacs.6b07014","article-title":"Through-Space Charge Interaction Substituent Effects in Molecular Catalysis Leading to the Design of the Most Efficient Catalyst of CO2-to-CO Electrochemical Conversion","volume":"138","author":"Azcarate","year":"2016","journal-title":"J. Am. Chem. Soc."},{"key":"B4","doi-asserted-by":"publisher","first-page":"703","DOI":"10.1021\/cs501641z","article-title":"Electrolyte Dependence of CO2 Electroreduction: Tetraalkylammonium Ions Are Not Electrocatalysts","volume":"5","author":"Berto","year":"2015","journal-title":"ACS Catal."},{"key":"B5","doi-asserted-by":"publisher","first-page":"255","DOI":"10.1021\/ar020230d","article-title":"Bond Dissociation Energies of Organic Molecules","volume":"36","author":"Blanksby","year":"2003","journal-title":"Acc. Chem. Res."},{"key":"B6","doi-asserted-by":"publisher","first-page":"2","DOI":"10.1038\/s41467-021-23447-8","article-title":"Visible-light Photoredox-Catalyzed Umpolung Carboxylation of Carbonyl Compounds with CO2","volume":"12","author":"Cao","year":"2021","journal-title":"Nat. Commun."},{"key":"B7","doi-asserted-by":"publisher","first-page":"644","DOI":"10.1002\/cjoc.201700742","article-title":"Photochemical and Electrochemical Carbon Dioxide Utilization with Organic Compounds","volume":"36","author":"Cao","year":"2018","journal-title":"Chin. J. Chem."},{"key":"B8","doi-asserted-by":"publisher","first-page":"2056","DOI":"10.1002\/ejoc.201601485","article-title":"Hydrogen Atom Transfer (HAT): A Versatile Strategy for Substrate Activation in Photocatalyzed Organic Synthesis","volume":"2017","author":"Capaldo","year":"2017","journal-title":"Eur. J. Org. Chem."},{"key":"B9","doi-asserted-by":"publisher","first-page":"5813","DOI":"10.1021\/acsaem.0c00728","article-title":"Carboxylation of \u03b1,\u03b2-Unsaturated Ketones by CO2 Fixation through Photoelectro-Chemistry","volume":"3","author":"Chen","year":"2020","journal-title":"ACS Appl. Energ. Mater."},{"key":"B10","doi-asserted-by":"publisher","first-page":"3056","DOI":"10.1002\/cssc.201801063","article-title":"Transition Metal-free CO2 Fixation into New Carbon-Carbon Bonds","volume":"11","author":"Cherubini-Celli","year":"2018","journal-title":"ChemSusChem"},{"key":"B11","doi-asserted-by":"publisher","first-page":"452","DOI":"10.1246\/bcsj.67.452","article-title":"Carboxylation of Active Methylene Compounds Using Anilide, Potassium Carbonate, and Carbon Dioxide","volume":"67","author":"Chiba","year":"1994","journal-title":"Bcsj"},{"key":"B12","doi-asserted-by":"publisher","first-page":"923","DOI":"10.1246\/cl.1992.923","article-title":"The Carboxylation of Active Methylene Compounds with Carbon Dioxide in the Presence of 18-Crown-6 and Potassium Carbonate","volume":"21","author":"Chiba","year":"1992","journal-title":"Chem. Lett."},{"key":"B13","doi-asserted-by":"publisher","first-page":"197","DOI":"10.1016\/0022-0728(90)80035-5","article-title":"CO2 Reduction at Platinum, Gold and Glassy Carbon Electrodes in Acetonitrile","volume":"288","author":"Christensen","year":"1990","journal-title":"J. Electroanalytical Chem. Interfacial Electrochemistry"},{"key":"B14","doi-asserted-by":"publisher","first-page":"12365","DOI":"10.1039\/d1sc02413b","article-title":"Suppressing Carboxylate Nucleophilicity with Inorganic Salts Enables Selective Electrocarboxylation without Sacrificial Anodes","volume":"12","author":"Corbin","year":"2021","journal-title":"Chem. Sci."},{"key":"B15","doi-asserted-by":"publisher","first-page":"2601","DOI":"10.1021\/acs.accounts.8b00525","article-title":"Uncovering the Complexity of the Simplest Atom Transfer Reaction","volume":"51","author":"Costas","year":"2018","journal-title":"Acc. Chem. Res."},{"key":"B16","doi-asserted-by":"publisher","first-page":"878","DOI":"10.3891\/acta.chem.scand.49-0878","article-title":"Estimation of the pKa for Some Hydrocarbons and Aldehydes and Solvation Energies of the Corresponding Anions","volume":"49","author":"Daasbjerg","year":"1995","journal-title":"Acta Chem. Scand."},{"key":"B17","doi-asserted-by":"publisher","first-page":"13490","DOI":"10.1002\/anie.202002341","article-title":"Transition\u2010Metal\u2010Free Carbon Isotope Exchange of Phenyl Acetic Acids","volume":"59","author":"Destro","year":"2020","journal-title":"Angew. Chem. Int. Ed."},{"key":"B18","doi-asserted-by":"publisher","first-page":"2679","DOI":"10.1021\/jo802641r","article-title":"First-Principles Calculation of pKa Values for Organic Acids in Nonaqueous Solution","volume":"74","author":"Ding","year":"2009","journal-title":"J. Org. Chem."},{"key":"B19","doi-asserted-by":"publisher","first-page":"G3073","DOI":"10.1149\/2.008307jes","article-title":"Electrocatalytic Activation of Aromatic Carbon-Bromine Bonds toward Carboxylation at Silver and Copper Cathodes","volume":"160","author":"Durante","year":"2013","journal-title":"J. Electrochem. Soc."},{"key":"B20","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1038\/s41467-018-07351-2","article-title":"Visible Light-Promoted CO2 Fixation with Imines to Synthesize Diaryl \u03b1-amino Acids","volume":"9","author":"Fan","year":"2018","journal-title":"Nat. Commun."},{"key":"B21","doi-asserted-by":"publisher","first-page":"101721","DOI":"10.1016\/j.jcou.2021.101721","article-title":"Performance of Supported Metal Catalysts in the Dimethyl Carbonate Production by Direct Synthesis Using CO2 and Methanol","volume":"53","author":"Faria","year":"2021","journal-title":"J. CO2 Utilization"},{"key":"B22","doi-asserted-by":"publisher","first-page":"1375","DOI":"10.1039\/c4gc01959h","article-title":"Sustainable Conversion of Carbon Dioxide: The Advent of Organocatalysis","volume":"17","author":"Fiorani","year":"2015","journal-title":"Green. Chem."},{"key":"B23","doi-asserted-by":"publisher","first-page":"4631","DOI":"10.1021\/acs.chemrev.7b00459","article-title":"Homogeneously Catalyzed Electroreduction of Carbon Dioxide-Methods, Mechanisms, and Catalysts","volume":"118","author":"Francke","year":"2018","journal-title":"Chem. Rev."},{"key":"B24","volume-title":"Gaussian 16","author":"Frisch","year":"2016"},{"key":"B25","doi-asserted-by":"publisher","first-page":"7227","DOI":"10.1021\/ja0421856","article-title":"Quantum-chemical Predictions of Absolute Standard Redox Potentials of Diverse Organic Molecules and Free Radicals in Acetonitrile","volume":"127","author":"Fu","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"B26","doi-asserted-by":"publisher","first-page":"1337","DOI":"10.1002\/cssc.201700205","article-title":"Photochemical Carboxylation of Activated C(sp3)\u2212H Bonds with CO2","volume":"10","author":"Gui","year":"2017","journal-title":"ChemSusChem"},{"key":"B27","doi-asserted-by":"publisher","first-page":"77","DOI":"10.1039\/d0gc03465g","article-title":"Recent Developments in Organocatalysed Transformations of Epoxides and Carbon Dioxide into Cyclic Carbonates","volume":"23","author":"Guo","year":"2021","journal-title":"Green. Chem."},{"key":"B28","doi-asserted-by":"publisher","first-page":"7301","DOI":"10.1039\/d0gc02743j","article-title":"Photocarboxylation with CO2: an Appealing and Sustainable Strategy for CO2 Fixation","volume":"22","author":"He","year":"2020","journal-title":"Green. Chem."},{"key":"B29","doi-asserted-by":"publisher","first-page":"41","DOI":"10.1016\/S0022-0728(02)00815-X","article-title":"Electrochemical Reduction and Carboxylation of Halobenzophenones","volume":"526","author":"Isse","year":"2002","journal-title":"J. Electroanalytical Chem."},{"key":"B30","doi-asserted-by":"publisher","first-page":"D113","DOI":"10.1149\/1.1490358","article-title":"Electrochemical Synthesis of Cyanoacetic Acid from Chloroacetonitrile and Carbon Dioxide","volume":"149","author":"Isse","year":"2002","journal-title":"J. Electrochem. Soc."},{"key":"B31","doi-asserted-by":"publisher","first-page":"241","DOI":"10.1016\/S0022-0728(97)00572-X","article-title":"Mechanism of the Electrochemical Reduction of Benzyl Chlorides Catalysed by Co(salen)","volume":"444","author":"Isse","year":"1998","journal-title":"J. Electroanalytical Chem."},{"key":"B32","volume-title":"Acid-base Dissociation Constants in Dipolar Aprotic Solvents","author":"Izutzu","year":"1990"},{"key":"B33","doi-asserted-by":"publisher","first-page":"987","DOI":"10.1055\/s-0037-1611738","article-title":"Aldehyde Carboxylation: A Concise DFT Mechanistic Study and a Hypothetical Role of CO2 in the Origin of Life","volume":"30","author":"Juhl","year":"2019","journal-title":"Synlett"},{"key":"B34","doi-asserted-by":"publisher","first-page":"12318","DOI":"10.1002\/anie.201806569","article-title":"Umpolung Reactivity of Aldehydes toward Carbon Dioxide","volume":"57","author":"Juhl","year":"2018","journal-title":"Angew. Chem. Int. Ed."},{"key":"B35","doi-asserted-by":"publisher","first-page":"7944","DOI":"10.1002\/chem.201300552","article-title":"Computed CH Acidity of Biaryl Compounds and Their Deprotonative Metalation by Using a Mixed lithium\/Zinc-TMP Base","volume":"19","author":"Kadiyala","year":"2013","journal-title":"Chem. Eur. J."},{"key":"B36","doi-asserted-by":"publisher","first-page":"557","DOI":"10.1126\/science.abb4129","article-title":"Direct Reversible Decarboxylation from Stable Organic Acids in Dimethylformamide Solution","volume":"369","author":"Kong","year":"2020","journal-title":"Science"},{"key":"B37","doi-asserted-by":"publisher","first-page":"403","DOI":"10.1016\/s0022-0728(77)80143-5","article-title":"Standard Potential and Kinetic Parameters of the Electrochemical Reduction of Carbon Dioxide in Dimethylformamide","volume":"78","author":"Lamy","year":"1977","journal-title":"J. Electroanalytical Chem. Interfacial Electrochemistry"},{"key":"B38","doi-asserted-by":"publisher","first-page":"8383","DOI":"10.1021\/jacs.0c01960","article-title":"From Carbodiimides to Carbon Dioxide: Quantification of the Electrophilic Reactivities of Heteroallenes","volume":"142","author":"Li","year":"2020","journal-title":"J. Am. Chem. Soc."},{"key":"B39","doi-asserted-by":"publisher","first-page":"1","DOI":"10.1038\/ncomms6933","article-title":"Using Carbon Dioxide as a Building Block in Organic Synthesis","volume":"6","author":"Liu","year":"2015","journal-title":"Nat. Commun."},{"key":"B40","doi-asserted-by":"publisher","first-page":"1302","DOI":"10.1002\/anie.201912455","article-title":"Naphthochromenones: Organic Bimodal Photocatalysts Engaging in Both Oxidative and Reductive Quenching Processes","volume":"59","author":"Mateos","year":"2020","journal-title":"Angew. Chem. Int. Ed."},{"key":"B41","doi-asserted-by":"publisher","first-page":"5816","DOI":"10.1039\/d1ee00228g","article-title":"Electrocatalytic CO2 Reduction: Role of the Cross-Talk at Nano-Carbon Interfaces","volume":"14","author":"Melchionna","year":"2021","journal-title":"Energy Environ. Sci."},{"key":"B42","doi-asserted-by":"publisher","first-page":"13426","DOI":"10.1002\/anie.201706724","article-title":"Carboxylation of Aromatic and Aliphatic Bromides and Triflates with CO2 by Dual Visible-Light-Nickel Catalysis","volume":"56","author":"Meng","year":"2017","journal-title":"Angew. Chem. Int. Ed."},{"key":"B43","doi-asserted-by":"publisher","DOI":"10.1021\/acs.joc.1c00821","article-title":"Integrated Flow Synthesis of \u03b1-Amino Acids by In Situ Generation of Aldimines and Subsequent Electrochemical Carboxylation","volume":"1","author":"Naito","year":"2021","journal-title":"J. Org. Chem."},{"key":"B44","doi-asserted-by":"publisher","first-page":"1065","DOI":"10.1021\/jo951702n","article-title":"Reductive Photocarboxylation of Phenanthrene: A Mechanistic Investigation","volume":"61","author":"Nikolaitchik","year":"1996","journal-title":"J. Org. Chem."},{"key":"B45","doi-asserted-by":"publisher","first-page":"1514","DOI":"10.1039\/c0gc00065e","article-title":"Synthesis of Cyclic Carbonates from Epoxides and CO2","volume":"12","author":"North","year":"2010","journal-title":"Green. Chem."},{"key":"B46","doi-asserted-by":"publisher","first-page":"7194","DOI":"10.1021\/acs.orglett.1c02592","article-title":"Photocatalytic Carbinol Cation\/Anion Umpolung: Direct Addition of Aromatic Aldehydes and Ketones to Carbon Dioxide","volume":"23","author":"Okumura","year":"2021","journal-title":"Org. Lett."},{"key":"B47","doi-asserted-by":"publisher","first-page":"3555","DOI":"10.1021\/acs.joc.0c02952","article-title":"Nucleophilicity Prediction via Multivariate Linear Regression Analysis","volume":"86","author":"Orlandi","year":"2021","journal-title":"J. Org. Chem."},{"key":"B48","doi-asserted-by":"publisher","first-page":"2171","DOI":"10.1016\/j.tetlet.2006.01.113","article-title":"CO2 Anion-Radical in Organic Carboxylations","volume":"47","author":"Otero","year":"2006","journal-title":"Tetrahedron Lett."},{"key":"B49","doi-asserted-by":"publisher","first-page":"1035","DOI":"10.1021\/np9904509","article-title":"Flavonoids as Antioxidants","volume":"63","author":"Pietta","year":"2000","journal-title":"J. Nat. Prod."},{"key":"B50","doi-asserted-by":"publisher","first-page":"217","DOI":"10.1039\/p29960000217","article-title":"Influence of Magnesium(II) Ions on Cathodic Reactions in Aprotic Solvents-Carboxylation of Methyl Aryl Ketones","volume":"2","author":"Pletcher","year":"1996","journal-title":"J. Chem. Soc. Perkin Trans"},{"key":"B52","doi-asserted-by":"publisher","first-page":"17142","DOI":"10.1021\/jacs.9b05895","article-title":"Rapid and Accurate Prediction of pKa Values of C-H Acids Using Graph Convolutional Neural Networks","volume":"141","author":"Roszak","year":"2019","journal-title":"J. Am. Chem. Soc."},{"key":"B53","doi-asserted-by":"publisher","first-page":"3414","DOI":"10.1021\/acscatal.0c05681","article-title":"CO2-Promoted Reactions: An Emerging Concept for the Synthesis of Fine Chemicals and Pharmaceuticals","volume":"11","author":"Sahoo","year":"2021","journal-title":"ACS Catal."},{"key":"B54","doi-asserted-by":"publisher","first-page":"13026","DOI":"10.1039\/c4cc04962d","article-title":"The Crucial Roles of MgCl2 as a Non-innocent Additive in the Ni-Catalyzed Carboxylation of Benzyl Halide with CO2","volume":"50","author":"Sayyed","year":"2014","journal-title":"Chem. Commun."},{"key":"B55","doi-asserted-by":"publisher","first-page":"2658","DOI":"10.1016\/j.chempr.2020.08.022","article-title":"Redox-Neutral Photocatalytic C\u2212H Carboxylation of Arenes and Styrenes with CO2","volume":"6","author":"Schmalzbauer","year":"2020","journal-title":"Chem"},{"key":"B56","doi-asserted-by":"publisher","first-page":"634","DOI":"10.1016\/j.electacta.2008.07.012","article-title":"Electrocatalytic Carboxylation of Chloroacetonitrile at a Silver Cathode for the Synthesis of Cyanoacetic Acid","volume":"54","author":"Scialdone","year":"2008","journal-title":"Electrochimica Acta"},{"key":"B57","doi-asserted-by":"publisher","first-page":"862","DOI":"10.5796\/electrochemistry.79.862","article-title":"Electrochemical Carboxylation of Flavones: Facile Synthesis of Flavanone-2-Carboxylic Acids","volume":"79","author":"Senboku","year":"2011","journal-title":"Electrochemistry"},{"key":"B58","doi-asserted-by":"publisher","first-page":"450","DOI":"10.1016\/j.electacta.2012.03.131","article-title":"Some Mechanistic Studies on Electrochemical Carboxylation of Flavones to Yield Flavanone-2-Carboxylic Acids","volume":"82","author":"Senboku","year":"2012","journal-title":"Electrochimica Acta"},{"key":"B59","doi-asserted-by":"publisher","first-page":"453","DOI":"10.1038\/nchem.2690","article-title":"Photoredox Activation of Carbon Dioxide for Amino Acid Synthesis in Continuous Flow","volume":"9","author":"Seo","year":"2017","journal-title":"Nat. Chem"},{"key":"B60","doi-asserted-by":"publisher","first-page":"21832","DOI":"10.1002\/anie.202105490","article-title":"Selective Electrosynthetic Hydrocarboxylation of \u03b1,\u03b2\u2010Unsaturated Esters with Carbon Dioxide**","volume":"60","author":"Sheta","year":"2021","journal-title":"Angew. Chem. Int. Ed."},{"key":"B61","doi-asserted-by":"publisher","first-page":"5196","DOI":"10.3390\/molecules15085196","article-title":"Photochemistry of Flavonoids","volume":"15","author":"Sisa","year":"2010","journal-title":"Molecules"},{"key":"B62","doi-asserted-by":"publisher","first-page":"19526","DOI":"10.1002\/anie.202102262","article-title":"Acridinium Salts and Cyanoarenes as Powerful Photocatalysts: Opportunities in Organic Synthesis","volume":"60","author":"Tlili","year":"2021","journal-title":"Angew. Chem. Int. Ed."},{"key":"B63","doi-asserted-by":"publisher","first-page":"508","DOI":"10.1002\/mrc.2783","article-title":"Radical Anions of Flavonoids","volume":"49","author":"Vakulskaya","year":"2011","journal-title":"Magn. Reson. Chem."},{"key":"B64","doi-asserted-by":"publisher","first-page":"987","DOI":"10.1007\/s11144-019-01544-6","article-title":"Chemical Fixation of CO2: the Influence of Linear Amphiphilic Anions on Surface Active Ionic Liquids (SAILs) as Catalysts for Synthesis of Cyclic Carbonates under Solvent-free Conditions","volume":"126","author":"Vieira","year":"2019","journal-title":"Reac Kinet Mech. Cat"},{"key":"B65","doi-asserted-by":"publisher","first-page":"108","DOI":"10.1007\/s10562-017-2212-4","article-title":"Surface Active Ionic Liquids as Catalyst for CO2 Conversion to Propylene Carbonate","volume":"148","author":"Vieira","year":"2018","journal-title":"Catal. Lett."},{"key":"B66","doi-asserted-by":"publisher","first-page":"1313","DOI":"10.1021\/acscatal.7b03396","article-title":"Hydricity of Transition-Metal Hydrides: Thermodynamic Considerations for CO2 Reduction","volume":"8","author":"Waldie","year":"2018","journal-title":"ACS Catal."},{"key":"B67","doi-asserted-by":"publisher","first-page":"1380","DOI":"10.1002\/ajoc.201700233","article-title":"Computational and Experimental Study on Electrocarboxylation of Benzalacetone","volume":"6","author":"Wang","year":"2017","journal-title":"Asian J. Org. Chem."},{"key":"B68","doi-asserted-by":"publisher","first-page":"8655","DOI":"10.1021\/acs.chemrev.6b00168","article-title":"Thermodynamic Hydricity of Transition Metal Hydrides","volume":"116","author":"Wiedner","year":"2016","journal-title":"Chem. Rev."},{"key":"B69","doi-asserted-by":"publisher","first-page":"2120","DOI":"10.1021\/ja00112a037","article-title":"Reduction of Di-tert-butyl Peroxide: Evidence for Nonadiabatic Dissociative Electron Transfer","volume":"117","author":"Workentin","year":"1995","journal-title":"J. Am. Chem. Soc."},{"key":"B70","doi-asserted-by":"publisher","first-page":"52","DOI":"10.1002\/cssc.201402837","article-title":"Upgrading Carbon Dioxide by Incorporation into Heterocycles","volume":"8","author":"Yu","year":"2015","journal-title":"ChemSusChem"},{"key":"B71","doi-asserted-by":"publisher","first-page":"21150","DOI":"10.1002\/anie.202101667","article-title":"Coupling Strategy for CO 2 Valorization Integrated with Organic Synthesis by Heterogeneous Photocatalysis","volume":"60","author":"Yuan","year":"2021","journal-title":"Angew. Chem. Int. Ed."},{"key":"B72","doi-asserted-by":"publisher","first-page":"10871","DOI":"10.1021\/acscatal.0c03127","article-title":"Visible-Light-Driven Catalytic Reductive Carboxylation with CO2","volume":"10","author":"Zhang","year":"2020","journal-title":"ACS Catal."},{"key":"B73","doi-asserted-by":"publisher","first-page":"233","DOI":"10.1021\/jacsau.0c00110","article-title":"Solvation Induction of Free Energy Barriers of Decarboxylation Reactions in Aqueous Solution from Dual-Level QM\/MM Simulations","volume":"1","author":"Zhou","year":"2021","journal-title":"JACS Au"},{"key":"B74","doi-asserted-by":"publisher","first-page":"7762","DOI":"10.1021\/acs.chemrev.7b00020","article-title":"Chalcone: A Privileged Structure in Medicinal Chemistry","volume":"117","author":"Zhuang","year":"2017","journal-title":"Chem. Rev."}],"container-title":["Frontiers in Chemistry"],"original-title":[],"link":[{"URL":"https:\/\/www.frontiersin.org\/articles\/10.3389\/fchem.2021.783993\/full","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2021,11,30]],"date-time":"2021-11-30T22:55:13Z","timestamp":1638312913000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.frontiersin.org\/articles\/10.3389\/fchem.2021.783993\/full"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,11,24]]},"references-count":73,"alternative-id":["10.3389\/fchem.2021.783993"],"URL":"https:\/\/doi.org\/10.3389\/fchem.2021.783993","relation":{},"ISSN":["2296-2646"],"issn-type":[{"value":"2296-2646","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,11,24]]},"article-number":"783993"}}