{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,8,22]],"date-time":"2026-08-22T15:27:07Z","timestamp":1787412427478,"version":"build-2736575974"},"reference-count":42,"publisher":"American Chemical Society (ACS)","issue":"33","license":[{"start":{"date-parts":[[2026,8,6]],"date-time":"2026-08-06T00:00:00Z","timestamp":1785974400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-029"},{"start":{"date-parts":[[2026,8,6]],"date-time":"2026-08-06T00:00:00Z","timestamp":1785974400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-037"},{"start":{"date-parts":[[2026,8,6]],"date-time":"2026-08-06T00:00:00Z","timestamp":1785974400000},"content-version":"stm-asf","delay-in-days":0,"URL":"https:\/\/doi.org\/10.15223\/policy-045"}],"funder":[{"DOI":"10.13039\/501100004608","name":"Jiangsu Provincial Department of Science and Technology","doi-asserted-by":"publisher","award":["BK20240960"],"award-info":[{"award-number":["BK20240960"]}],"id":[{"id":"10.13039\/501100004608","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100006407","name":"Science and Technology Department of Henan Province","doi-asserted-by":"publisher","award":["252300423755"],"award-info":[{"award-number":["252300423755"]}],"id":[{"id":"10.13039\/501100006407","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100008868","name":"Jiangsu Provincial Department of Science and Technology","doi-asserted-by":"publisher","award":["BE2023693"],"award-info":[{"award-number":["BE2023693"]}],"id":[{"id":"10.13039\/501100008868","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100018922","name":"Advanced Catalysis and Green Manufacturing Collaborative Innovation Center, Changzhou University","doi-asserted-by":"publisher","award":["NA"],"award-info":[{"award-number":["NA"]}],"id":[{"id":"10.13039\/501100018922","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":[],"published-print":{"date-parts":[[2026,8,21]]},"abstract":"<jats:title>Abstract<\/jats:title>\n                  <jats:p>This work presents a ruthenium complex catalyst bearing redox-active ligands for highly selective oxidative cleavage of alkenes. The ligand serves as a dynamic electron reservoir with two core functions. Reversible electron transfer between the ligand and the Ru center generates high-valent Ru(V)\u2550O\/Ru(VI) active species to drive C\u2550C bond scission. Meanwhile, stable coordination modulates the metal\u2019s electron density and steric environment, suppressing ligand decomposition and overoxidation of aldehyde intermediates into carboxylic acids. Conducted at room temperature in an ethyl acetate\u2013water mixed solvent, the optimized system delivers outstanding chemoselectivity: C\u2550C substrates are selectively cleaved into aldehydes, whereas C\u2261C substrates are converted to \u03b1-diketones. The catalyst features wide substrate compatibility, efficiently transforming monoterpenes, amino acid derivatives, and nonsteroidal anti-inflammatory drugs. This study establishes an efficient route for selective functional group modification of structurally intricate molecules.<\/jats:p>","DOI":"10.1021\/acs.joc.6c00705","type":"journal-article","created":{"date-parts":[[2026,8,7]],"date-time":"2026-08-07T01:01:27Z","timestamp":1786064487000},"page":"11274-11285","source":"Crossref","is-referenced-by-count":0,"title":["Redox-Active Ligand-Assisted\nRuthenium-Catalyzed Lemieux\u2013Johnson-Type\nOxidation of Olefins for Aldehyde Synthesis"],"prefix":"10.1021","volume":"91","author":[{"given":"Zhiyu","family":"Zhang","sequence":"first","affiliation":[{"name":"Changzhou University , , ,","place":["Changzhou, China, 213164"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Panpan","family":"Li","sequence":"additional","affiliation":[{"name":"Changzhou University , , ,","place":["Changzhou, China, 213164"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Zhengyi","family":"Li","sequence":"additional","affiliation":[{"name":"Changzhou University , , ,","place":["Changzhou, China, 213164"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-8592-2711","authenticated-orcid":true,"given":"Ying-Ying","family":"Li","sequence":"additional","affiliation":[{"name":"Zhengzhou Normal University , , ,","place":["Zhengzhou, China, 450044"]}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-4548-5799","authenticated-orcid":true,"given":"Jing","family":"Shi","sequence":"additional","affiliation":[{"name":"Changzhou University , , ,","place":["Changzhou, China, 213164"]}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"316","published-online":{"date-parts":[[2026,8,6]]},"reference":[{"key":"2026082211143108900_cit1","doi-asserted-by":"publisher","first-page":"81","DOI":"10.1038\/s41586-022-05211-0","article-title":"Photoexcited Nitroarenes\nfor the Oxidative Cleavage of Alkenes","volume":"610","author":"Ruffoni","year":"2022","journal-title":"Nature"},{"key":"2026082211143108900_cit2","doi-asserted-by":"publisher","first-page":"2411","DOI":"10.1021\/cr050989d","article-title":"Chemical Routes\nfor the Transformation\nof Biomass into Chemicals","volume":"107","author":"Corma","year":"2007","journal-title":"Chem. Rev."},{"key":"2026082211143108900_cit3","doi-asserted-by":"publisher","first-page":"149","DOI":"10.1016\/j.catcom.2013.06.008","article-title":"Mixed Cu-Ni-Co\nNano-Metal Oxides:\nA New Class of Catalysts for Styrene Oxidation","volume":"40","author":"Valand","year":"2013","journal-title":"Catal. Commun."},{"key":"2026082211143108900_cit4","doi-asserted-by":"publisher","first-page":"106822","DOI":"10.1016\/j.bioorg.2023.106822","article-title":"Synthesis, Biological and Molecular\nDocking Studies\nof Pyrimidine-Derived Bioactive Schiff Bases","volume":"140","author":"Manzoor","year":"2023","journal-title":"Bioorg. Chem."},{"key":"2026082211143108900_cit5","doi-asserted-by":"publisher","first-page":"146762","DOI":"10.1016\/j.ijbiomac.2025.146762","article-title":"The Soy Protein Isolate-based\nFilms Enhanced with Quaternary Ammonium Salt Lignin-Cinnamaldehyde\nComposite Particles Via Multiple Cross-Linking of Hydrogen and Chemical\nBonding","volume":"322","author":"Miao","year":"2025","journal-title":"Int. J. Biol. Macromol."},{"key":"2026082211143108900_cit6","doi-asserted-by":"publisher","first-page":"111814","DOI":"10.1016\/j.mcat.2021.111814","article-title":"Feasible Synthesis\nof Bifurfural from Renewable Furfural Derived 5-Bromofurfural for\nPolymerization","volume":"513","author":"Zhu","year":"2021","journal-title":"Mol. Catal."},{"issue":"1","key":"2026082211143108900_cit7","doi-asserted-by":"publisher","first-page":"10","DOI":"10.1016\/j.gee.2022.07.003","article-title":"Catalytic Conversion of Lignocellulosic Biomass into\nChemicals and\nFuels","volume":"8","author":"Deng","year":"2023","journal-title":"Green Energy Environ."},{"issue":"7","key":"2026082211143108900_cit8","doi-asserted-by":"publisher","first-page":"8695","DOI":"10.1021\/acsami.9b21058","article-title":"Thiophene-Based\nAldehyde Derivatives for Functionalizable and Adhesive Semiconducting\nPolymers","volume":"12","author":"Istif","year":"2020","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"2026082211143108900_cit9","doi-asserted-by":"publisher","first-page":"50","DOI":"10.1002\/chem.19960020111","article-title":"Ruthenium-Catalyzed\ncis-Dihydroxylation of Alkenes: Scope and Limitations","volume":"2","author":"Shing","year":"1996","journal-title":"Chem. - Eur. J."},{"key":"2026082211143108900_cit10","doi-asserted-by":"publisher","first-page":"7123","DOI":"10.1021\/jo034864p","article-title":"RuO4-Catalyzed\nKetohydroxylation of Olefins","volume":"68","author":"Plietker","year":"2003","journal-title":"J. Org. Chem."},{"issue":"40","key":"2026082211143108900_cit11","doi-asserted-by":"publisher","first-page":"13987","DOI":"10.1021\/ja5075294","article-title":"A Highly Efficient Catalyst for Selective Oxidative\nScission of Olefins to Aldehydes: Abnormal- NHC-Ru(II) Complex in\nOxidation Chemistry","volume":"136","author":"Daw","year":"2014","journal-title":"J. Am. Chem. Soc."},{"issue":"30","key":"2026082211143108900_cit12","doi-asserted-by":"publisher","first-page":"4233","DOI":"10.1016\/j.tet.2017.03.039","article-title":"Alkene Ozonolysis","volume":"73","author":"Fisher","year":"2017","journal-title":"Tetrahedron"},{"issue":"28","key":"2026082211143108900_cit13","doi-asserted-by":"publisher","first-page":"15138","DOI":"10.1002\/anie.202014974","article-title":"Criegee Intermediates\nBeyond Ozonolysis: Synthetic and Mechanistic Insights","volume":"60","author":"Hassan","year":"2021","journal-title":"Angew. Chem., Int. Ed."},{"issue":"8","key":"2026082211143108900_cit14","doi-asserted-by":"publisher","first-page":"588","DOI":"10.1021\/ar2000265","article-title":"Metal-Ligand Cooperation by Aromatization-Dearomatization:\nA New Paradigm in Bond Activation and \u201cGreen\u201d Catalysis","volume":"44","author":"Gunanathan","year":"2011","journal-title":"Acc. Chem. Res."},{"issue":"34","key":"2026082211143108900_cit15","doi-asserted-by":"publisher","first-page":"15437","DOI":"10.1021\/jacs.2c05648","article-title":"Photoinduced Oxygen Transfer Using\nNitroarenes for the Anaerobic Cleavage of Alkenes","volume":"144","author":"Wise","year":"2022","journal-title":"J. Am. Chem. Soc."},{"issue":"48","key":"2026082211143108900_cit16","doi-asserted-by":"publisher","first-page":"10235","DOI":"10.1021\/acs.orglett.4c03595","article-title":"Cyclometalated Ruthenium-Complex- Catalyzed Selective Oxidation of\nOlefins to Carbonyls","volume":"26","author":"Konwar","year":"2024","journal-title":"Org. Lett."},{"key":"2026082211143108900_cit17","doi-asserted-by":"publisher","first-page":"10005","DOI":"10.1021\/jacs.1c05757","article-title":"Oxidative Cleavage\nof Alkenes by O2 with a Non-Heme Manganese Catalyst","volume":"143","author":"Huang","year":"2021","journal-title":"J. Am. Chem. Soc."},{"issue":"36","key":"2026082211143108900_cit18","doi-asserted-by":"publisher","first-page":"12821","DOI":"10.1021\/jacs.7b07909","article-title":"Mechanistically Driven Development of an Iron Catalyst\nfor Selective Syn-Dihydroxylation of Alkenes with Aqueous Hydrogen\nPeroxide","volume":"139","author":"Borrell","year":"2017","journal-title":"J. Am. Chem. Soc."},{"key":"2026082211143108900_cit19","doi-asserted-by":"publisher","first-page":"87","DOI":"10.1016\/j.jorganchem.2016.02.015","article-title":"Synthesis and Characterization of\nPiano-Stool Ruthenium Complexes with N,N\u2019-Pyridine Imine Bidentate\nLigands and Their Application in Styrene Oxidation","volume":"808","author":"Gichumbi","year":"2016","journal-title":"J. Organomet. Chem."},{"key":"2026082211143108900_cit20","doi-asserted-by":"publisher","first-page":"277","DOI":"10.1007\/b94652","article-title":"Oxidation\nUsing Ruthenium Catalysts\nTop","volume":"11","author":"Kodama","year":"2004","journal-title":"Organomet. Chem."},{"key":"2026082211143108900_cit21","doi-asserted-by":"publisher","first-page":"9186","DOI":"10.1021\/jo001348f","article-title":"Ruthenium-Catalyzed\nOxidation of Alkanes with Tert-Butyl Hydroperoxide and Peracetic Acid","volume":"65","author":"Murahashi","year":"2000","journal-title":"J. Org. Chem."},{"key":"2026082211143108900_cit22","doi-asserted-by":"publisher","first-page":"8932","DOI":"10.1002\/anie.202002014","article-title":"Donor-Flexible\nBis- (Pyridylidene\nAmide) Ligands for Highly Efficient Ruthenium-Catalyzed Olefin Oxidation","volume":"59","author":"Salzmann","year":"2020","journal-title":"Angew. Chem., Int. Ed."},{"key":"2026082211143108900_cit23","doi-asserted-by":"publisher","first-page":"3335","DOI":"10.1039\/D1SC06355C","article-title":"Catalysis\nwith Cycloruthenated Complexes","volume":"13","author":"Findlay","year":"2022","journal-title":"Chem. Sci."},{"key":"2026082211143108900_cit24","doi-asserted-by":"publisher","first-page":"1981","DOI":"10.1021\/acs.chemrev.9b00634","article-title":"N-Heterocyclic Carbene\nComplexes in C-H Activation Reactions","volume":"120","author":"Zhao","year":"2020","journal-title":"Chem.\nRev."},{"key":"2026082211143108900_cit25","doi-asserted-by":"publisher","first-page":"478","DOI":"10.1021\/jo01110a606","article-title":"Notes-Osmium Tetroxide-Catalyzed\nPeriodate Oxidation of Olefinic Bonds","volume":"21","author":"Pappo","year":"1956","journal-title":"J. Org.\nChem."},{"key":"2026082211143108900_cit26","doi-asserted-by":"publisher","first-page":"2683","DOI":"10.1002\/cctc.201900242","article-title":"Remote \u2018Imidazole\u2019\nBased Ruthenium(II) p-Cymene Precatalyst for Selective Oxidative Cleavage\nof C-C Multiple Bonds","volume":"11","author":"Dutta","year":"2019","journal-title":"ChemCatchem"},{"key":"2026082211143108900_cit27","doi-asserted-by":"publisher","first-page":"97107","DOI":"10.1039\/C6RA19044H","article-title":"Synthesis\nand characterisation of\ncycloruthenated benzhydrazone complexes: catalytic application to\nselective oxidative cleavage of olefins to aldehydes","volume":"6","author":"Manikandan","year":"2016","journal-title":"RSC Adv."},{"key":"2026082211143108900_cit28","doi-asserted-by":"publisher","first-page":"8468","DOI":"10.1021\/acs.joc.9b00487","article-title":"(Ar-tpy)RuII(ACN)3: A Water-Soluble\nCatalyst for Aldehyde Amidation, Olefin Oxo-Scissoring, and Alkyne\nOxygenation","volume":"84","author":"Joarder","year":"2019","journal-title":"J. Org. Chem."},{"key":"2026082211143108900_cit29","doi-asserted-by":"publisher","first-page":"112014","DOI":"10.1016\/j.mcat.2021.112014","article-title":"Functionalized-1,3,4-Oxadiazole\nLigands for the Ruthenium-Catalyzed Lemieux-Johnson Type Oxidation\nof Olefins and Alkynes in Water","volume":"517","author":"Hkiri","year":"2022","journal-title":"Mol. Catal."},{"issue":"4","key":"2026082211143108900_cit30","doi-asserted-by":"publisher","first-page":"1399","DOI":"10.3390\/molecules27041399","article-title":"Electrocatalytic\nCO2 Reduction and H2 Evolution by a Copper (II)\nComplex\nwith Redox-Active Ligand","volume":"27","author":"Li","year":"2022","journal-title":"Molecules"},{"issue":"20","key":"2026082211143108900_cit31","doi-asserted-by":"publisher","first-page":"13075","DOI":"10.1021\/acscatal.2c02655","article-title":"Ligand-Based\nRedox: Catalytic Applications\nand Mechanistic Aspects","volume":"12","author":"Singh","year":"2022","journal-title":"ACS Catal."},{"issue":"7","key":"2026082211143108900_cit32","doi-asserted-by":"publisher","first-page":"3755","DOI":"10.1021\/acs.inorgchem.6c00520","article-title":"Proton-Coupled Electron\nTransfer in Coordination Chemistry","volume":"65","author":"Matson","year":"2026","journal-title":"Inorg. Chem."},{"issue":"5","key":"2026082211143108900_cit33","doi-asserted-by":"publisher","first-page":"990","DOI":"10.1021\/ja993385y","article-title":"Galactose\nOxidase Pro-Sequence Cleavage and Cofactor Assembly Are Self-Processing\nReactions","volume":"122","author":"Rogers","year":"2000","journal-title":"J. Am. Chem. Soc."},{"issue":"10","key":"2026082211143108900_cit34","doi-asserted-by":"publisher","first-page":"148059","DOI":"10.1016\/j.bbabio.2019.148059","article-title":"Mechanism of Protonation\nof the Over-reduced Mn4CaO5 Cluster in Photosystem\nII","volume":"1860","author":"Saito","year":"2019","journal-title":"Biochim. Biophys. Acta, Bioenerg."},{"key":"2026082211143108900_cit35","doi-asserted-by":"publisher","first-page":"4442","DOI":"10.1039\/b815547j","article-title":"Alcohol\nCross-Coupling Reactions Catalyzed By Ru and Ir Terpyridine Complexes","volume":"6","author":"Gnanamgari","year":"2008","journal-title":"Org. Biomol. Chem."},{"issue":"12","key":"2026082211143108900_cit36","doi-asserted-by":"publisher","first-page":"7468","DOI":"10.1021\/acs.inorgchem.8b01095","article-title":"Sterically Demanding Phosphines with\n2,6-Dibenzhydryl-4-methylphenyl Core: Synthesis of Ru(II), Pd(II),\nand Pt(II) Complexes, and Structural and Catalytic Studies","volume":"57","author":"Pandey","year":"2018","journal-title":"Inorg. Chem."},{"issue":"8","key":"2026082211143108900_cit37","doi-asserted-by":"publisher","first-page":"3750","DOI":"10.1021\/acs.inorgchem.5b02518","article-title":"Photocatalytic Oxygenation\nof Sulfide and Alkenes by Trinuclear Ruthenium Clusters","volume":"55","author":"Phungsripheng","year":"2016","journal-title":"Inorg. Chem."},{"issue":"6","key":"2026082211143108900_cit38","doi-asserted-by":"publisher","first-page":"1184","DOI":"10.1021\/acs.orglett.3c04263","article-title":"Cyclometalated\nRuthenium Catalyst Enables Selective\nOxidation of N-Substituted Tetrahydroquinolines to Lactams","volume":"26","author":"Konwar","year":"2024","journal-title":"Org. Lett."},{"issue":"7","key":"2026082211143108900_cit39","doi-asserted-by":"publisher","DOI":"10.1002\/ajoc.202500201","article-title":"Structurally\nMMO Active Site-Like Ruthenium Complex for Catalytic Oxidation of\nOlefins to Aldehydes","volume":"14","author":"Xie","year":"2025","journal-title":"Asian J. Org. Chem."},{"key":"2026082211143108900_cit40","doi-asserted-by":"publisher","first-page":"140159","DOI":"10.1016\/j.molstruc.2024.140159","article-title":"Synthesis\nand Reactivity of Isomeric\nRu Complexes with Hydroxypyridyl Fragment: Active Catalysts for \u03b2Alkylation\nof Secondary Alcohols with Primary Alcohols","volume":"1321","author":"Shi","year":"2025","journal-title":"J. Mol. Struct."},{"key":"2026082211143108900_cit41","doi-asserted-by":"publisher","first-page":"2109","DOI":"10.1039\/DT9920002109","article-title":"Synthesis,\nStructure, Reactivity and Electrochemistry\nof cis-Dioxoruthenium-(VI) and-(V) Complexes containing N,N,N\u2019,N\u2019,3,6-Hexamethyl-3,6-diazaoctane-1,8-diamine","author":"Li","year":"1992","journal-title":"J. Chem. Soc., Dalton Trans."},{"key":"2026082211143108900_cit42","doi-asserted-by":"publisher","first-page":"16727","DOI":"10.1039\/C6DT03024F","article-title":"Characteristics and reactivity of\nruthenium-oxo complexes","volume":"45","author":"Ishizuka","year":"2016","journal-title":"Dalton Trans."}],"container-title":["The Journal of Organic Chemistry"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/pubs.acs.org\/doi\/pdf\/10.1021\/acs.joc.6c00705","content-type":"application\/pdf","content-version":"vor","intended-application":"unspecified"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/91\/33\/11274\/66451872\/acs.joc.6c00705.pdf","content-type":"application\/pdf","content-version":"vor","intended-application":"syndication"},{"URL":"https:\/\/pubs.acs.org\/joceah\/article-pdf\/91\/33\/11274\/66451872\/acs.joc.6c00705.pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2026,8,22]],"date-time":"2026-08-22T15:15:36Z","timestamp":1787411736000},"score":1,"resource":{"primary":{"URL":"https:\/\/pubs.acs.org\/joceah\/article\/91\/33\/11274\/5249841\/Redox-Active-Ligand-Assisted-Ruthenium-Catalyzed"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2026,8,6]]},"references-count":42,"journal-issue":{"issue":"33","published-online":{"date-parts":[[2026,8,6]]},"published-print":{"date-parts":[[2026,8,21]]}},"URL":"https:\/\/doi.org\/10.1021\/acs.joc.6c00705","relation":{},"ISSN":["0022-3263","1520-6904"],"issn-type":[{"value":"0022-3263","type":"print"},{"value":"1520-6904","type":"electronic"}],"subject":[],"published":{"date-parts":[[2026,8,6]]}}}