{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T15:04:36Z","timestamp":1790348676049,"version":"4.1.0"},"reference-count":46,"publisher":"American Chemical Society (ACS)","issue":"38","license":[{"start":{"date-parts":[[2026,9,14]],"date-time":"2026-09-14T00:00:00Z","timestamp":1789344000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,9,14]],"date-time":"2026-09-14T00:00:00Z","timestamp":1789344000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,9,14]],"date-time":"2026-09-14T00:00:00Z","timestamp":1789344000000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100012600","name":"ShanghaiTech University","doi-asserted-by":"publisher","id":[{"id":"10.13039\/501100012600","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,9,25]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>We report a mechanochemical Corey\u2013Chaykovsky epoxidation that converts aldehydes and ketones to epoxides within minutes under an ambient atmosphere using sulfonium or sulfoxonium salts, KOH, and minimal liquid additives. The method accommodates a broad substrate scope, is readily scalable, and often enables simple extraction without chromatography. It further enables telescoped sulfonium generation\u2013oxidation\u2013epoxidation, tunable enone chemoselectivity, and direct conversion of imines to unstabilized aziridines. An unexpected dependence of reactivity on the ylide precursor halide reveals distinct mechanochemical reactivity from that under conventional solution-phase conditions.<\/jats:p>","DOI":"10.1021\/acs.orglett.6c03622","type":"journal-article","created":{"date-parts":[[2026,9,14]],"date-time":"2026-09-14T16:02:09Z","timestamp":1789401729000},"page":"12084-12089","source":"Crossref","is-referenced-by-count":0,"title":["Ultrafast Mechanochemical\nEpoxidation of Aldehydes\nand Ketones"],"prefix":"10.1021","volume":"28","author":[{"given":"Zhongye","family":"Huang","sequence":"first","affiliation":[{"name":"ShanghaiTech University , , ,","place":["Shanghai, China, 201210"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Xinhan","family":"Liu","sequence":"additional","affiliation":[{"name":"ShanghaiTech University , , ,","place":["Shanghai, China, 201210"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6963-6099","authenticated-orcid":true,"given":"KaKing","family":"Yan","sequence":"additional","affiliation":[{"name":"ShanghaiTech University , , ,","place":["Shanghai, China, 201210"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,9,14]]},"reference":[{"key":"2026092510114743700_cit1","doi-asserted-by":"publisher","first-page":"8153","DOI":"10.1021\/cr500036t","article-title":"The Chemistry of\nTransition Metals with Three-Membered\nRing Heterocycles","volume":"114","author":"Huang","year":"2014","journal-title":"Chem. Rev."},{"key":"2026092510114743700_cit2","doi-asserted-by":"publisher","first-page":"9172","DOI":"10.1039\/D1GC03029A","article-title":"Organocatalytic Epoxidation and Allylic\nOxidation of Alkenes by Molecular Oxygen","volume":"23","author":"Petsi","year":"2021","journal-title":"Green\nChem."},{"key":"2026092510114743700_cit3","doi-asserted-by":"publisher","first-page":"16248","DOI":"10.1021\/jacs.5c01400","article-title":"Oxa-\u03c0,\u03c3-Methane\nRearrangement Approach for Epoxide Synthesis","volume":"147","author":"Wang","year":"2025","journal-title":"J. Am. Chem. Soc."},{"key":"2026092510114743700_cit4","doi-asserted-by":"publisher","first-page":"8877","DOI":"10.1038\/s41467-024-53049-z","article-title":"Universal High-Efficiency Electrocatalytic\nOlefin Epoxidation via a Surface-Confined Radical Promotion","volume":"15","author":"Ran","year":"2024","journal-title":"Nat. Commun."},{"key":"2026092510114743700_cit5","doi-asserted-by":"publisher","first-page":"3227","DOI":"10.1002\/adsc.202300181","article-title":"Continuous Synthesis\nof Epoxides from Alkenes by Hydrogen Peroxide with Titanium Silicalite-1\nCatalyst Using Flow Reactors","volume":"365","author":"Kon","year":"2023","journal-title":"Adv. Synth. Catal."},{"key":"2026092510114743700_cit6","doi-asserted-by":"publisher","first-page":"7821","DOI":"10.1038\/s41467-026-74592-x","article-title":"Enzyme-Inspired\nSingle-Molecule\nPhotocatalyst Enables Singlet-Oxygen-Driven Asymmetric Epoxidation\nand Sulfoximination","volume":"17","author":"Chen","year":"2026","journal-title":"Nat. Commun."},{"key":"2026092510114743700_cit7","doi-asserted-by":"publisher","first-page":"102794","DOI":"10.1016\/j.xcrp.2025.102794","article-title":"Enzymatic\nEpoxidation Strategies for the Stereoselective Synthesis of Chiral\nEpoxides","volume":"6","author":"Petkevic\u030cius","year":"2025","journal-title":"Cell Rep. Phys. Sci."},{"key":"2026092510114743700_cit8","doi-asserted-by":"publisher","first-page":"1504","DOI":"10.1021\/ja01212a034","article-title":"Hydroxylation\nand Epoxidation of\nSome 1-Olefins with Per-acids","volume":"68","author":"Swern","year":"1946","journal-title":"J. Am. Chem.\nSoc."},{"key":"2026092510114743700_cit9","doi-asserted-by":"publisher","first-page":"378","DOI":"10.1021\/acs.chas.2c00025","article-title":"Feasibility\nof a Selective Epoxidation Technique for Use in Quantification of\nPeracetic Acid in Air Samples Collected on Sorbent Tubes","volume":"29","author":"Walsh","year":"2022","journal-title":"ACS Chem. Health Saf."},{"key":"2026092510114743700_cit10","doi-asserted-by":"publisher","first-page":"866","DOI":"10.1021\/ja00864a039","article-title":"Methylsulfinylcarbanion","volume":"84","author":"Corey","year":"1962","journal-title":"J. Am.\nChem. Soc."},{"key":"2026092510114743700_cit11","doi-asserted-by":"publisher","first-page":"37125","DOI":"10.1039\/D5RA04921K","article-title":"A Review on the Sulfur\nYlide-Mediated Corey-Chaykovsky Reaction: a Powerful Approach to Natural\nProduct Synthesis","volume":"15","author":"Ammara","year":"2025","journal-title":"RSC Adv."},{"key":"2026092510114743700_cit12","doi-asserted-by":"publisher","first-page":"611","DOI":"10.1021\/ar030045f","article-title":"Catalytic, Asymmetric\nSulfur Ylide-Mediated Epoxidation\nof Carbonyl Compounds: Scope, Selectivity, and Applications in Synthesis","volume":"37","author":"Aggarwal","year":"2004","journal-title":"Acc. Chem. Res."},{"key":"2026092510114743700_cit13","doi-asserted-by":"publisher","first-page":"2210","DOI":"10.1021\/acs.oprd.9b00276","article-title":"Explosion\nHazards of Sodium Hydride in Dimethyl Sulfoxide, N,N-Dimethylformamide,\nand N,N-Dimethylacetamide","volume":"23","author":"Yang","year":"2019","journal-title":"Org. Process Res.\nDev."},{"key":"2026092510114743700_cit14","doi-asserted-by":"publisher","first-page":"413","DOI":"10.1039\/C1CS15171A","article-title":"Mechanochemistry: Opportunities for\nNew and Cleaner Synthesis","volume":"41","author":"James","year":"2012","journal-title":"Chem. Soc. Rev."},{"key":"2026092510114743700_cit15","doi-asserted-by":"publisher","first-page":"4007","DOI":"10.1021\/acs.joc.6b02887","article-title":"Altering Product Selectivity\nby Mechanochemistry","volume":"82","author":"Herna\u0301ndez","year":"2017","journal-title":"J. Org. Chem."},{"key":"2026092510114743700_cit16","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202401376","article-title":"Organic Reactions\nEnabled by Mechanical Force-Induced Single Electron\nTransfer","volume":"30","author":"Liu","year":"2024","journal-title":"Chem. - Eur. J."},{"key":"2026092510114743700_cit17","doi-asserted-by":"publisher","first-page":"1018","DOI":"10.1002\/anie.201906755","article-title":"Mechanochemistry for Synthesis","volume":"59","author":"Fris\u030cc\u030cic\u0301","year":"2020","journal-title":"Angew. Chem. Int. Ed."},{"key":"2026092510114743700_cit18","doi-asserted-by":"publisher","DOI":"10.1002\/cssc.202200362","article-title":"Mechanochemistry: New Tools to Navigate\nthe Uncharted Territory of \u201cImpossible\u201d Reactions","volume":"15","author":"Cuccu","year":"2022","journal-title":"ChemSusChem"},{"key":"2026092510114743700_cit19","doi-asserted-by":"publisher","first-page":"51","DOI":"10.1038\/s41570-022-00442-1","article-title":"Advancing\nMechanochemical Synthesis by Combining Milling with Different Energy\nSources","volume":"7","author":"Martinez","year":"2023","journal-title":"Nat. Rev. Chem."},{"key":"2026092510114743700_cit20","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202503061","article-title":"Mechanochemical\nStrategies Applied to the Late-Stage\nModifications of Pharmaceutically Active Compounds","volume":"64","author":"Templ","year":"2025","journal-title":"Angew. Chem. Int. Ed."},{"key":"2026092510114743700_cit21","doi-asserted-by":"publisher","first-page":"2145","DOI":"10.1002\/cssc.202100478","article-title":"Sustainability Assessment of Mechanochemistry by Using\nthe Twelve Principles of Green Chemistry","volume":"14","author":"Ardila-Fierro","year":"2021","journal-title":"ChemSusChem"},{"key":"2026092510114743700_cit22","doi-asserted-by":"publisher","first-page":"6680","DOI":"10.1039\/D2CS00997H","article-title":"Green Metrics in Mechanochemistry","volume":"52","author":"Fantozzi","year":"2023","journal-title":"Chem. Soc. Rev."},{"key":"2026092510114743700_cit23","doi-asserted-by":"publisher","first-page":"669","DOI":"10.1038\/s41467-025-67299-y","article-title":"Upcycling of PTFE and\nPVDF to Fluorochemicals Through Mechanochemical Process","volume":"17","author":"Hattori","year":"2026","journal-title":"Nat. Commun."},{"key":"2026092510114743700_cit24","doi-asserted-by":"publisher","first-page":"40895","DOI":"10.1021\/jacs.5c14052","article-title":"A Reductive\nMechanochemical Approach Enabling Direct Upcycling of Fluoride from\nPolytetrafluoroethylene (PTFE) into Fine Chemicals","volume":"147","author":"Lowe","year":"2025","journal-title":"J. Am. Chem. Soc."},{"key":"2026092510114743700_cit25","doi-asserted-by":"publisher","first-page":"4131","DOI":"10.1038\/s41467-026-70813-5","article-title":"Unlocking the Reducing\nPower of Metal Nitrides by Mechanochemical Hydrodefluorination of\nFluorinated Compounds","volume":"17","author":"Chen","year":"2026","journal-title":"Nat. Commun."},{"key":"2026092510114743700_cit26","doi-asserted-by":"publisher","first-page":"100","DOI":"10.1038\/s41586-025-08698-5","article-title":"Phosphate-Enabled\nMechanochemical\nPFAS Destruction for Fluoride Reuse","volume":"640","author":"Yang","year":"2025","journal-title":"Nature"},{"key":"2026092510114743700_cit27","doi-asserted-by":"publisher","first-page":"1062","DOI":"10.1021\/jacs.3c12049","article-title":"Using Mechanochemistry\nto Activate Commodity Plastics as Initiators for Radical Chain Reactions\nof Small Organic Molecules","volume":"146","author":"Kubota","year":"2024","journal-title":"J. Am. Chem. Soc."},{"key":"2026092510114743700_cit28","doi-asserted-by":"publisher","first-page":"6165","DOI":"10.1021\/jacs.1c00906","article-title":"Tackling Solubility\nIssues in Organic Synthesis: Solid-State Cross-Coupling of Insoluble\nAryl Halides","volume":"143","author":"Seo","year":"2021","journal-title":"J. Am. Chem. Soc."},{"key":"2026092510114743700_cit29","doi-asserted-by":"publisher","first-page":"14803","DOI":"10.1021\/acscatal.1c03731","article-title":"Palladium-Catalyzed Solid-State Polyfluoroarylation\nof Aryl Halides Using Mechanochemistry","volume":"11","author":"Takahashi","year":"2021","journal-title":"ACS\nCatal."},{"key":"2026092510114743700_cit30","doi-asserted-by":"publisher","first-page":"669","DOI":"10.1038\/s44160-025-00949-7","article-title":"Mechanochemical Synthesis of Organosodium\nCompounds through Direct Sodiation of Organic Halides","volume":"5","author":"Kondo","year":"2026","journal-title":"Nat. Synth."},{"key":"2026092510114743700_cit31","doi-asserted-by":"publisher","first-page":"13681","DOI":"10.1021\/acscatal.2c03117","article-title":"Mechanical\nActivation\nof Zero-Valent Metal Reductants for Nickel-Catalyzed Cross-Electrophile\nCoupling","volume":"12","author":"Jones","year":"2022","journal-title":"ACS Catal."},{"key":"2026092510114743700_cit32","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202411536","article-title":"High-Energy\nBall Milling Enables an Ultra-Fast Wittig\nOlefination Under Ambient and Solvent-Free Conditions","volume":"63","author":"Templ","year":"2024","journal-title":"Angew. Chem. Int. Ed."},{"key":"2026092510114743700_cit33","doi-asserted-by":"publisher","first-page":"8559","DOI":"10.1038\/s41467-026-75499-3","article-title":"Machine Learning-Assisted Development\nof a Fast Mechanochemical Johnson\u2013Corey\u2013Chaykovsky Reaction","volume":"17","author":"Mele","year":"2026","journal-title":"Nat. Commun."},{"key":"2026092510114743700_cit35","doi-asserted-by":"publisher","first-page":"129888","DOI":"10.1016\/j.jhazmat.2022.129888","article-title":"Tuning the Olefin-VOCs Epoxidation Performance of Ceria by Mechanochemical\nLoading of Coinage Metal","volume":"441","author":"Xiong","year":"2023","journal-title":"J. Hazard. Mater."},{"key":"2026092510114743700_cit36","doi-asserted-by":"publisher","first-page":"1246","DOI":"10.1002\/adsc.202001245","article-title":"Liquid-Assisted\nGrinding Mechanochemistry in the Synthesis\nof Pharmaceuticals","volume":"363","author":"Ying","year":"2021","journal-title":"Adv. Synth. Catal."},{"key":"2026092510114743700_cit37","doi-asserted-by":"publisher","first-page":"3879","DOI":"10.1021\/acs.chemmater.0c00041","article-title":"Tuning\nMorphology and Properties of Epoxy-Based Solid-State\nPolymer Electrolytes by Molecular Interaction for Flexible All-Solid-State\nSupercapacitors","volume":"32","author":"Song","year":"2020","journal-title":"Chem. Mater."},{"key":"2026092510114743700_cit38","doi-asserted-by":"publisher","first-page":"3425","DOI":"10.1021\/jo00411a049","article-title":"Synthesis of Aryloxiranes","volume":"43","author":"Yang","year":"1978","journal-title":"J. Org. Chem."},{"key":"2026092510114743700_cit39","doi-asserted-by":"publisher","first-page":"647","DOI":"10.1021\/ma302241w","article-title":"Ferrocenyl Glycidyl\nEther: A Versatile Ferrocene Monomer for Copolymerization with Ethylene\nOxide to Water-Soluble, Thermoresponsive Copolymers","volume":"46","author":"Tonhauser","year":"2013","journal-title":"Macromolecules"},{"key":"2026092510114743700_cit40","doi-asserted-by":"publisher","DOI":"10.1002\/anie.202217418","article-title":"Controlling\nthe Fluorescence Performance of AIE Polymers by Controlling the Polymer\nMicrostructure","volume":"62","author":"Xu","year":"2023","journal-title":"Angew. Chem. Int. Ed."},{"key":"2026092510114743700_cit41","doi-asserted-by":"publisher","first-page":"3964","DOI":"10.3390\/polym15193964","article-title":"Brief Overview on\nEpoxies in Electronics: Properties,\nApplications, and Modifications","volume":"15","author":"Dallaev","year":"2023","journal-title":"Polymers"},{"key":"2026092510114743700_cit42","doi-asserted-by":"publisher","first-page":"4222","DOI":"10.1021\/jo00278a045","article-title":"Camphoryl\nSulfide as a Chiral Auxiliary\nand a Mediator for One-step Synthesis of Optically Active 1,2-Diaryloxiranes","volume":"54","author":"Furukawa","year":"1989","journal-title":"J. Org. Chem."},{"key":"2026092510114743700_cit43","doi-asserted-by":"publisher","first-page":"5747","DOI":"10.1021\/ja025633n","article-title":"Unraveling the Mechanism of Epoxide\nFormation from Sulfur Ylides and Aldehydes","volume":"124","author":"Aggarwal","year":"2002","journal-title":"J. Am. Chem. Soc."},{"key":"2026092510114743700_cit44","doi-asserted-by":"publisher","first-page":"1646","DOI":"10.1063\/1.1730669","article-title":"Lattice Energies\nof the Alkali Halides and the Electron Affinities of the Halogens","volume":"31","author":"Cubicciotti","year":"1959","journal-title":"J. Chem. Phys."},{"key":"2026092510114743700_cit45","doi-asserted-by":"publisher","DOI":"10.1002\/chem.202500798","article-title":"Advances in Mechanochemical Methods for One-Pot Multistep\nOrganic Synthesis","volume":"31","author":"Biedermann","year":"2025","journal-title":"Chem. - Eur. J."},{"key":"2026092510114743700_cit46","doi-asserted-by":"publisher","first-page":"10476","DOI":"10.1039\/D4CC04150J","article-title":"Construction\nof Stable Porous Organic Cages: From the\nPerspective of Chemical Bonds","volume":"60","author":"Yang","year":"2024","journal-title":"Chem. Commun."},{"key":"2026092510114743700_cit47","doi-asserted-by":"publisher","first-page":"881","DOI":"10.1038\/s41570-022-00437-y","article-title":"Imine and Imine-Derived\nLinkages\nin Two-Dimensional Covalent Organic Frameworks","volume":"6","author":"Qian","year":"2022","journal-title":"Nat. Rev. Chem."}],"container-title":["Organic Letters"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.orglett.6c03622","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/orlef7\/article-pdf\/28\/38\/12084\/68503067\/acs.orglett.6c03622.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/orlef7\/article-pdf\/28\/38\/12084\/68503067\/acs.orglett.6c03622.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,9,25]],"date-time":"2026-09-25T14:49:42Z","timestamp":1790347782000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/orlef7\/article\/28\/38\/12084\/5429578\/Ultrafast-Mechanochemical-Epoxidation-of-Aldehydes"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,9,14]]},"references-count":46,"journal-issue":{"issue":"38","published-online":{"date-parts":[[2026,9,14]]},"published-print":{"date-parts":[[2026,9,25]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.orglett.6c03622","relation":{},"ISSN":["1523-7060","1523-7052"],"issn-type":[{"value":"1523-7060","type":"print"},{"value":"1523-7052","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,9,14]]}}}