{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,19]],"date-time":"2026-08-19T18:18:45Z","timestamp":1787163525098,"version":"build-2736575974"},"reference-count":75,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2021,1,22]],"date-time":"2021-01-22T00:00:00Z","timestamp":1611273600000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100004040","name":"KU Leuven","doi-asserted-by":"publisher","award":["C14\/19\/78"],"award-info":[{"award-number":["C14\/19\/78"]}],"id":[{"id":"10.13039\/501100004040","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>4-Sulfonyl-1,2,3-triazole scaffolds possess promising bioactivities and applications as anion binders. However, these structures remain relatively unexplored and efficient synthetic procedures for their synthesis remain desirable. A practical room-temperature, aerobic copper-catalyzed three-component reaction of aromatic ketones, sodium sulfinates, and azides is reported. This procedure allows for facile access to 4-sulfonyl-1,5-disubstituted-1,2,3-triazoles in yields ranging from 34 to 89%. The reaction proceeds via a sequential aerobic copper(II)chloride-catalyzed oxidative sulfonylation and the Dimroth azide\u2013enolate cycloaddition.<\/jats:p>","DOI":"10.3390\/molecules26030581","type":"journal-article","created":{"date-parts":[[2021,1,22]],"date-time":"2021-01-22T11:13:53Z","timestamp":1611314033000},"page":"581","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["The Three-Component Synthesis of 4-Sulfonyl-1,2,3-triazoles via a Sequential Aerobic Copper-Catalyzed Sulfonylation and Dimroth Cyclization"],"prefix":"10.3390","volume":"26","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-5396-9892","authenticated-orcid":false,"given":"Max","family":"Van Hoof","sequence":"first","affiliation":[{"name":"Molecular Design and Synthesis, Department of Chemistry, KU Leuven, 3001 Leuven, Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Santhini Pulikkal","family":"Veettil","sequence":"additional","affiliation":[{"name":"Molecular Design and Synthesis, Department of Chemistry, KU Leuven, 3001 Leuven, Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-9597-0629","authenticated-orcid":false,"given":"Wim","family":"Dehaen","sequence":"additional","affiliation":[{"name":"Molecular Design and Synthesis, Department of Chemistry, KU Leuven, 3001 Leuven, Belgium"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2021,1,22]]},"reference":[{"key":"ref_1","first-page":"1139","article-title":"Microwave-Assisted One-Pot Synthesis of Benzo[d]Thiazole Containing 1,2,3-Triazoles by Using Organo Catalytic Reaction and Their Antibacterial Activity","volume":"7","author":"Narsimha","year":"2017","journal-title":"Heterocycl. Lett."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"60","DOI":"10.1016\/j.ejmech.2016.02.013","article-title":"Azide-Enolate 1,3-Dipolar Cycloaddition in the Synthesis of Novel Triazole-Based Miconazole Analogues as Promising Antifungal Agents","volume":"112","year":"2016","journal-title":"Eur. J. Med. Chem."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"2258","DOI":"10.1039\/C7MD00442G","article-title":"Synthesis and Antifungal Activity of Novel Oxazolidin-2-One-Linked 1,2,3-Triazole Derivatives","volume":"8","year":"2017","journal-title":"MedChemComm"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"6184","DOI":"10.1021\/jo00100a019","article-title":"Steric Effects on the Regioselectivity of an Azide-Alkyne Dipolar Cycloaddition Reaction: The Synthesis of Human Leukocyte Elastase Inhibitors","volume":"59","author":"Hlasta","year":"1994","journal-title":"J. Org. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"741","DOI":"10.1038\/s41467-017-00780-5","article-title":"SPA70 Is a Potent Antagonist of Human Pregnane X Receptor","volume":"8","author":"Lin","year":"2017","journal-title":"Nat. Commun."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"345","DOI":"10.1124\/mol.119.116616","article-title":"Mechanistic Insights of Phenobarbital-Mediated Activation of Human but Not Mouse Pregnane X Receptor","volume":"96","author":"Li","year":"2019","journal-title":"Mol. Pharmacol."},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"Huber, A.D., Wright, W.C., Lin, W., Majumder, K., Low, J.A., Wu, J., Buchman, C.D., Pintel, D.J., and Chen, T. (2020). Mutation of a Single Amino Acid of Pregnane X Receptor Switches an Antagonist to Agonist by Altering AF-2 Helix Positioning. Cell. Mol. Life Sci.","DOI":"10.1007\/s00018-020-03505-y"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"3341","DOI":"10.1021\/acs.joc.7b00261","article-title":"Sulfur Groups Improve the Performance of Triazole- and Triazolium-Based Interaction Units in Anion Binding","volume":"82","author":"Velado","year":"2017","journal-title":"J. Org. Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"8057","DOI":"10.1021\/jo801621d","article-title":"1,3-Dipolar Cycloadditions of Acetylenic Sulfones in Solution and on Solid Supports","volume":"73","author":"Gao","year":"2008","journal-title":"J. Org. Chem."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"5367","DOI":"10.1016\/j.bmc.2010.05.040","article-title":"1H-1,2,3-Triazol-1-Yl Thiodigalactoside Derivatives as High Affinity Galectin-3 Inhibitors","volume":"18","author":"Salameh","year":"2010","journal-title":"Bioorg. Med. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"1877","DOI":"10.1002\/anie.201309855","article-title":"Iridium-Catalyzed Intermolecular Azide\u2014Alkyne Cycloaddition of Internal Thioalkynes under Mild Conditions","volume":"53","author":"Ding","year":"2014","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"10766","DOI":"10.1002\/anie.201705006","article-title":"Ruthenium-Catalyzed Azide\u2014Thioalkyne Cycloadditions in Aqueous Media: A Mild, Orthogonal, and Biocompatible Chemical Ligation","volume":"56","author":"Destito","year":"2017","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"6705","DOI":"10.1021\/acs.orglett.8b02794","article-title":"Regiodivergent Rhodium(I)-Catalyzed Azide\u2014Alkyne Cycloaddition (RhAAC) to Access Either Fully Substituted Sulfonyl-1,2,3-Triazoles under Mild Conditions","volume":"20","author":"Song","year":"2018","journal-title":"Org. Lett."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"393","DOI":"10.1016\/0040-4039(93)85084-A","article-title":"Alkynyl Sulfides and Selenides from Alkynyl Bromides and Diorganoyl Chalcogenides Promoted by Copper(I) Iodide","volume":"34","author":"Braga","year":"1993","journal-title":"Tetrahedron Lett."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"1196","DOI":"10.1021\/ol500067f","article-title":"The Reaction of Grignard Reagents with Bunte Salts: A Thiol-Free Synthesis of Sulfides","volume":"16","author":"Reeves","year":"2014","journal-title":"Org. Lett."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"16563","DOI":"10.1021\/ja5083014","article-title":"Fast and Highly Chemoselective Alkynylation of Thiols with Hypervalent Iodine Reagents Enabled Through a Low Energy Barrier Concerted Mechanism","volume":"136","author":"Frei","year":"2014","journal-title":"J. Am. Chem. Soc."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"6021","DOI":"10.1021\/acs.orglett.9b02174","article-title":"N-Alkynylthio Phthalimide: A Shelf-Stable Alkynylthio Transfer Reagent for the Synthesis of Alkynyl Thioethers","volume":"21","author":"Gao","year":"2019","journal-title":"Org. Lett."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"4156","DOI":"10.1039\/C4OB00556B","article-title":"Improving Alkynyl(Aryl)Iodonium Salts: 2-Anisyl as a Superior Aryl Group","volume":"12","author":"Hamnett","year":"2014","journal-title":"Org. Biomol. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"1875","DOI":"10.1002\/asia.201700550","article-title":"MnO2-Promoted Oxidative Radical Sulfonylation of Haloalkynes with Sulfonyl Hydrazides: C(Sp)\u2013S Bond Formation towards Alkynyl Sulfones","volume":"12","author":"Chen","year":"2017","journal-title":"Chem. Asian J."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2656","DOI":"10.1021\/acs.orglett.5b01037","article-title":"A Direct Metal-Free Decarboxylative Sulfono Functionalization (DSF) of Cinnamic Acids to \u03b1,\u03b2-Unsaturated Phenyl Sulfones","volume":"17","author":"Singh","year":"2015","journal-title":"Org. Lett."},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Pokhodylo, N.T., Matiychuk, V.S., and Obushak, M.D. (2009). (Arylsulfonyl)Acetones and -Acetonitriles: New Activated Methylenic Building Blocks for Synthesis of 1,2,3-Triazoles. Synthesis Stuttgart., 2321\u20132323.","DOI":"10.1055\/s-0029-1216850"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"6206","DOI":"10.1021\/acs.orglett.5b03196","article-title":"Room-Temperature Organocatalytic Cycloaddition of Azides with \u03b2-Keto Sulfones: Toward Sulfonyl-1,2,3-Triazoles","volume":"17","author":"Saraiva","year":"2015","journal-title":"Org. Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"7045","DOI":"10.1002\/slct.201801344","article-title":"Enamine-Mediated Azide-Ketone [3+2] Cycloaddition of Azidoperfluoroalkanes","volume":"3","author":"Blastik","year":"2018","journal-title":"ChemistrySelect"},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"1835","DOI":"10.1080\/00397911.2020.1757113","article-title":"Dihydro-2H-Thiopyran-3(4H)-One-1,1-Dioxide\u2014A New Cyclic Ketomethylenic Reagent for the Dimroth-Type 1,2,3-Triazole Synthesis","volume":"50","author":"Pokhodylo","year":"2020","journal-title":"Synth. Commun."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"1693","DOI":"10.1055\/s-0031-1290952","article-title":"IBX\/I2-Mediated Reaction of Sodium Arenesulfinates with Alkenes: Facile Synthesis of \u03b2-Keto Sulfones","volume":"44","author":"Samakkanad","year":"2012","journal-title":"Synthesis Stuttgart."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"18391","DOI":"10.1038\/srep18391","article-title":"Ligand-Mediated and Copper-Catalyzed C(Sp3)-H Bond Functionalization of Aryl Ketones with Sodium Sulfinates under Mild Conditions","volume":"5","author":"Lan","year":"2015","journal-title":"Sci. Rep."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"4205","DOI":"10.1002\/anie.201311217","article-title":"Copper-Catalyzed Coupling of Oxime Acetates with Sodium Sulfinates: An Efficient Synthesis of Sulfone Derivatives","volume":"53","author":"Tang","year":"2014","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"3456","DOI":"10.1002\/ejoc.202000423","article-title":"A Naphthalimide-Based ND-O-EAc Photocatalyst for Sulfonation of Alkenes to Access \u03b2-Ketosulfones under Visible Light","volume":"2020","author":"Yang","year":"2020","journal-title":"Eur. J. Org. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"6557","DOI":"10.1021\/acs.orglett.0c02308","article-title":"Copper-Catalyzed Thiolation of Terminal Alkynes Employing Thiocyanate as the Sulfur Source Leading to Enaminone-Based Alkynyl Sulfides under Ambient Conditions","volume":"22","author":"Chandran","year":"2020","journal-title":"Org. Lett."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"464","DOI":"10.1021\/acs.orglett.9b04221","article-title":"Electrochemical Synthesis of \u03b2-Ketosulfones from Switchable Starting Materials","volume":"22","author":"Yavari","year":"2020","journal-title":"Org. Lett."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"634","DOI":"10.1039\/C8GC03671C","article-title":"One-Pot Synthesis of Chiral \u03b2-Hydroxysulfones from Alkynes via Aerobic Oxysulfonylation and Asymmetric Reduction in MeOH\/H2O","volume":"21","author":"Cui","year":"2019","journal-title":"Green Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"2329","DOI":"10.1021\/jo01031a055","article-title":"Terminal Benzoylation of Certain \u03b2-Oxo Sulfones to Form Dioxo Sulfones by Means of Sodium Hydride. Dibenzoylation of Dimethyl Sulfone","volume":"29","author":"Miles","year":"1964","journal-title":"J. Org. Chem."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"798","DOI":"10.1139\/v84-133","article-title":"The Preparation, Spectral Properties, Structures, and Base-Induced Cleavage Reactions of Some \u03b1-Halo-\u03b2-Ketosulfones","volume":"62","author":"Grossert","year":"1984","journal-title":"Can. J. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"5914","DOI":"10.1021\/acs.orglett.8b02579","article-title":"Nickel-Catalyzed Highly Enantioselective Hydrogenation of \u03b2-Acetylamino Vinylsulfones: Access to Chiral \u03b2-Amido Sulfones","volume":"20","author":"Long","year":"2018","journal-title":"Org. Lett."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"1443","DOI":"10.1021\/jo026636l","article-title":"Efficient Conversion of Sulfones into \u03b2-Keto Sulfones by N-Acylbenzotriazoles","volume":"68","author":"Katritzky","year":"2003","journal-title":"J. Org. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1698","DOI":"10.1002\/ajoc.201800340","article-title":"Metal-Free Three-Component Assembly of Fully Substituted 1,2,3-Triazoles","volume":"7","author":"Ahamad","year":"2018","journal-title":"Asian J. Org. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"4721","DOI":"10.1002\/ejoc.201900698","article-title":"\u03b1-Diazo-\u03b2-Oxosulfones as Partners in the Wolff 1,2,3-Triazole Synthesis and the Wolff Rearrangement in the Presence of Aromatic Amines","volume":"2019","author":"Safrygin","year":"2019","journal-title":"Eur. J. Org. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","unstructured":"Farrington, A., and Hough, L. (1965). A New Entry to Triazoles from Carbohydrates. Chem. Commun., 219\u2013220.","DOI":"10.1039\/c19650000219"},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"107","DOI":"10.1016\/S0008-6215(00)82342-3","article-title":"A Fused Pyrrolidotriazole Derivative from Bis(Ethylsulphonyl)-(2,3-O-Isopropylidene-4-O-Methanesulphonyl-\u03b1-D-Lyxopyranosyl)Methane","volume":"38","author":"Farrington","year":"1974","journal-title":"Carbohydr. Res."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"10155","DOI":"10.1002\/anie.201403453","article-title":"A Metal-Free Three-Component Reaction for the Regioselective Synthesis of 1,4,5-Trisubstituted 1,2,3-Triazoles","volume":"53","author":"Thomas","year":"2014","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"15934","DOI":"10.1038\/srep15934","article-title":"Tuning the Reactivity of Radical through a Triplet Diradical Cu(II) Intermediate in Radical Oxidative Cross-Coupling","volume":"5","author":"Zhou","year":"2015","journal-title":"Sci. Rep."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"3616","DOI":"10.1002\/adsc.201600693","article-title":"Copper-Mediated Oxidative Radical Addition\/Cyclization Cascade: Synthesis of Trifluoromethylated and Sulfonated Quinoline-2,4(1H,3H)-Diones","volume":"358","author":"Fu","year":"2016","journal-title":"Adv. Synth. Catal."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"1161","DOI":"10.1021\/acscatal.7b02974","article-title":"Oxidative Coupling Mechanisms: Current State of Understanding","volume":"8","author":"Maseras","year":"2018","journal-title":"ACS Catal."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"3900","DOI":"10.1039\/C5SC04590H","article-title":"Unraveling Innate Substrate Control in Site-Selective Palladium-Catalyzed C\u2013H Heterocycle Functionalization","volume":"7","author":"Choi","year":"2016","journal-title":"Chem. Sci."},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Itahara, T., Ikeda, M., and Sakakibara, T. (1983). Alkenylation of 1-Acylindoles with Olefins Bearing Electron-Withdrawing Substituents and Palladium Acetate. J. Chem. Soc. Perkin Trans. 1, 1361\u20131363.","DOI":"10.1039\/p19830001361"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"1756","DOI":"10.1021\/acs.accounts.5b00060","article-title":"Copper-Catalyzed Aerobic Oxidations of Organic Molecules: Pathways for Two-Electron Oxidation with a Four-Electron Oxidant and a One-Electron Redox-Active Catalyst","volume":"48","author":"McCann","year":"2015","journal-title":"Accounts Chem. Res."},{"key":"ref_47","doi-asserted-by":"crossref","unstructured":"Lei, A., Shi, W., Liu, C., Zhang, H., and He, C. (2016). Oxidative Cross-Coupling Reactions, WIley.","DOI":"10.1002\/9783527680986"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"3400","DOI":"10.1002\/anie.200300630","article-title":"Palladium Oxidase Catalysis: Selective Oxidation of Organic Chemicals by Direct Dioxygen-Coupled Turnover","volume":"43","author":"Stahl","year":"2004","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_49","doi-asserted-by":"crossref","unstructured":"Gligorich, K.M., and Sigman, M.S. (2009). Recent Advancements and Challenges of PalladiumII-Catalyzed Oxidation Reactions with Molecular Oxygen as the Sole Oxidant. Chem. Commun., 3854\u20133867.","DOI":"10.1039\/b902868d"},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"2778","DOI":"10.1039\/C4CY00544A","article-title":"Oxidative Coupling Reactions for the Functionalisation of C\u2013H Bonds Using Oxygen","volume":"4","author":"Gulzar","year":"2014","journal-title":"Catal. Sci. Technol."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"2636","DOI":"10.1021\/acs.chemrev.7b00334","article-title":"Ligand-Promoted Palladium-Catalyzed Aerobic Oxidation Reactions","volume":"118","author":"Wang","year":"2018","journal-title":"Chem. Rev."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.jcat.2008.08.012","article-title":"Aerobic Oxidation of Amines to Imines Catalyzed by Bulk Gold Powder and by Alumina-Supported Gold","volume":"260","author":"Zhu","year":"2008","journal-title":"J. Catal."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"177","DOI":"10.1039\/C1SC00619C","article-title":"Ruthenium-Catalyzed Aerobic Oxidative Coupling of Alkynes with 2-Aryl-Substituted Pyrroles","volume":"3","author":"Ackermann","year":"2012","journal-title":"Chem. Sci."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"6632","DOI":"10.1021\/ja050436k","article-title":"Heterogeneously Catalyzed Aerobic Oxidative Biaryl Coupling of 2-Naphthols and Substituted Phenols in Water","volume":"127","author":"Matsushita","year":"2005","journal-title":"J. Am. Chem. Soc."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"14462","DOI":"10.1021\/ja8049595","article-title":"Mechanistic Investigations of the Iridium(III)-Catalyzed Aerobic Oxidation of Primary and Secondary Alcohols","volume":"130","author":"Jiang","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"833","DOI":"10.1021\/ja077406x","article-title":"Copper-Catalyzed Aerobic Oxidative Amidation of Terminal Alkynes:\u2009 Efficient Synthesis of Ynamides","volume":"130","author":"Hamada","year":"2008","journal-title":"J. Am. Chem. Soc."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"851","DOI":"10.1021\/ar2002045","article-title":"Overcoming the \u201cOxidant Problem\u201d: Strategies to Use O2 as the Oxidant in Organometallic C\u2013H Oxidation Reactions Catalyzed by Pd (and Cu)","volume":"45","author":"Campbell","year":"2012","journal-title":"Accounts Chem. Res."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"e1500656","DOI":"10.1126\/sciadv.1500656","article-title":"Copper-Catalyzed Aerobic Oxidative Coupling: From Ketone and Diamine to Pyrazine","volume":"1","author":"Wu","year":"2015","journal-title":"Sci. Adv."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"165","DOI":"10.1080\/00397911.2015.1121546","article-title":"Copper Nitrate\u2013Catalyzed \u03b1-Bromination of Aryl Ketones with Hydrobromic Acid","volume":"46","author":"Wang","year":"2016","journal-title":"Synth. Commun."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"110460","DOI":"10.1016\/j.mcat.2019.110460","article-title":"Synthesis of Ti-Al Binary Oxides and Their Catalytic Application for C-H Halogenation of Phenols, Aldehydes and Ketones","volume":"475","author":"Su","year":"2019","journal-title":"Mol. Catal."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"9797","DOI":"10.1021\/ja4026424","article-title":"Divergence between Organometallic and Single-Electron-Transfer Mechanisms in Copper(II)-Mediated Aerobic C\u2013H Oxidation","volume":"135","author":"Suess","year":"2013","journal-title":"J. Am. Chem. Soc."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"11062","DOI":"10.1002\/anie.201103945","article-title":"Copper-Catalyzed Aerobic Oxidative C\u2013H Functionalizations: Trends and Mechanistic Insights","volume":"50","author":"Wendlandt","year":"2011","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"3386","DOI":"10.1021\/jo00249a058","article-title":"Hydrolysis of Tosyl Esters Initiated by an Electron Transfer from Photoexcited Electron-Rich Aromatic Compounds","volume":"53","author":"Nishida","year":"1988","journal-title":"J. Org. Chem."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"6102","DOI":"10.1039\/c3cc41249k","article-title":"Copper-Catalyzed Sulfonamides Formation from Sodium Sulfinates and Amines","volume":"49","author":"Tang","year":"2013","journal-title":"Chem. Commun."},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"7372","DOI":"10.1021\/jo5010845","article-title":"Copper-Catalyzed Aerobic Decarboxylative Sulfonylation of Cinnamic Acids with Sodium Sulfinates: Stereospecific Synthesis of (E)-Alkenyl Sulfones","volume":"79","author":"Jiang","year":"2014","journal-title":"J. Org. Chem."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"2890","DOI":"10.1021\/acs.orglett.9b00907","article-title":"Copper(II)-Catalyzed Alkene Aminosulfonylation with Sodium Sulfinates for the Synthesis of Sulfonylated Pyrrolidones","volume":"21","author":"Rao","year":"2019","journal-title":"Org. Lett."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"2240","DOI":"10.1039\/C9QO00421A","article-title":"Iminyl Radical-Promoted Imino Sulfonylation, Imino Cyanogenation and Imino Thiocyanation of \u03b3,\u03b4-Unsaturated Oxime Esters: Synthesis of Versatile Functionalized Pyrrolines","volume":"6","author":"Wang","year":"2019","journal-title":"Org. Chem. Front."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1002\/bbpc.19800840109","article-title":"The Reversible Hydration of Carbonyl Compounds in Aqueous Solution. Part I, The Keto\/Gem-Diol Equilibrium","volume":"84","author":"Buschmann","year":"1980","journal-title":"Ber. Bunsenges. Phys. Chem."},{"key":"ref_69","first-page":"3","article-title":"Dimroth Reaction","volume":"36","year":"1971","journal-title":"Ind. Chim. Belge"},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"10797","DOI":"10.1039\/C5CC02319J","article-title":"Organocatalytic Routes toward Substituted 1,2,3-Triazoles","volume":"51","author":"John","year":"2015","journal-title":"Chem. Commun."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"10420","DOI":"10.1002\/anie.201406721","article-title":"An Organocatalytic Azide\u2013Aldehyde [3+2] Cycloaddition: High-Yielding Regioselective Synthesis of 1,4-Disubstituted 1,2,3-Triazoles","volume":"53","author":"Ramachary","year":"2014","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"7512","DOI":"10.1021\/jo971176v","article-title":"NMR Chemical Shifts of Common Laboratory Solvents as Trace Impurities","volume":"62","author":"Gottlieb","year":"1997","journal-title":"J. Org. Chem."},{"key":"ref_73","doi-asserted-by":"crossref","unstructured":"Campbell-Verduyn, L.S., Mirfeizi, L., Dierckx, R.A., Elsinga, P.H., and Feringa, B.L. (2009). Phosphoramidite Accelerated Copper(i)-Catalyzed [3+2] Cycloadditions of Azides and Alkynes. Chem. Commun., 2139\u20132141.","DOI":"10.1039\/b822994e"},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"513","DOI":"10.1016\/j.tetlet.2004.10.176","article-title":"One-Pot Approach for the Regioselective Synthesis of \u03b2-Keto Sulfones Based on Acid-Catalyzed Reaction of Sulfonyl Chlorides with Arylacetylenes and Water","volume":"46","author":"Lai","year":"2005","journal-title":"Tetrahedron Lett."},{"key":"ref_75","doi-asserted-by":"crossref","unstructured":"Qian, H., and Huang, X. (2006). Solid-Phase Synthesis of \u03b2-Keto Sulfones. Synthesis Stuttgart., 1934\u20131936.","DOI":"10.1055\/s-2006-942382"}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/3\/581\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,11]],"date-time":"2025-10-11T05:14:14Z","timestamp":1760159654000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/26\/3\/581"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2021,1,22]]},"references-count":75,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2021,2]]}},"alternative-id":["molecules26030581"],"URL":"https:\/\/doi.org\/10.3390\/molecules26030581","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2021,1,22]]}}}