{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,3,16]],"date-time":"2026-03-16T23:44:50Z","timestamp":1773704690248,"version":"3.50.1"},"reference-count":132,"publisher":"MDPI AG","issue":"15","license":[{"start":{"date-parts":[[2023,8,1]],"date-time":"2023-08-01T00:00:00Z","timestamp":1690848000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia","doi-asserted-by":"publisher","award":["UIDP\/50006\/2020"],"award-info":[{"award-number":["UIDP\/50006\/2020"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100001871","name":"Funda\u00e7\u00e3o para a Ci\u00eancia e Tecnologia","doi-asserted-by":"publisher","award":["SFRH\/BD\/151159\/2021"],"award-info":[{"award-number":["SFRH\/BD\/151159\/2021"]}],"id":[{"id":"10.13039\/501100001871","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["IJMS"],"abstract":"<jats:p>The catalytic epoxidation of small alkenes and allylic alcohols includes a wide range of valuable chemical applications, with many works describing vanadium complexes as suitable catalysts towards sustainable process chemistry. But, given the complexity of these mechanisms, it is not always easy to sort out efficient examples for streamlining sustainable processes and tuning product optimization. In this review, we provide an update on major works of tunable vanadium-catalyzed epoxidations, with a focus on sustainable optimization routes. After presenting the current mechanistic view on vanadium catalysts for small alkenes and allylic alcohols\u2019 epoxidation, we argue the key challenges in green process development by highlighting the value of updated kinetic and mechanistic studies, along with essential computational studies.<\/jats:p>","DOI":"10.3390\/ijms241512299","type":"journal-article","created":{"date-parts":[[2023,8,1]],"date-time":"2023-08-01T09:06:44Z","timestamp":1690880804000},"page":"12299","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":17,"title":["Systematic Development of Vanadium Catalysts for Sustainable Epoxidation of Small Alkenes and Allylic Alcohols"],"prefix":"10.3390","volume":"24","author":[{"ORCID":"https:\/\/orcid.org\/0000-0001-7226-8995","authenticated-orcid":false,"given":"Jos\u00e9","family":"Ferraz-Caetano","sequence":"first","affiliation":[{"name":"LAQV-REQUIMTE, Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, Rua do Campo Alegre, S\/N, 4169-007 Porto, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-8786-0086","authenticated-orcid":false,"given":"Filipe","family":"Teixeira","sequence":"additional","affiliation":[{"name":"CQUM, Centre of Chemistry, University of Minho, Campus de Gualtar, 4710-057 Braga, Portugal"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-3375-8670","authenticated-orcid":false,"given":"Maria Nat\u00e1lia Dias Soeiro","family":"Cordeiro","sequence":"additional","affiliation":[{"name":"LAQV-REQUIMTE, Department of Chemistry and Biochemistry, Faculty of Sciences, University of Porto, Rua do Campo Alegre, S\/N, 4169-007 Porto, Portugal"}]}],"member":"1968","published-online":{"date-parts":[[2023,8,1]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"289","DOI":"10.1021\/acsorginorgau.2c00009","article-title":"Epoxides: Small Rings to Play with under Asymmetric Organocatalysis","volume":"2","author":"Meninno","year":"2022","journal-title":"ACS Org. Inorg. Au"},{"key":"ref_2","unstructured":"Nielsen, L.P.C., and Jacobsen, E.N. (2006). Aziridines and Epoxides in Organic Synthesis, Wiley-VCH."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"6","DOI":"10.3998\/ark.5550190.0007.302","article-title":"Epoxides and aziridines\u2014A mini review","volume":"2006","author":"Padwa","year":"2005","journal-title":"ARKIVOC"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"707","DOI":"10.1351\/pac199062040707","article-title":"Novel processes for stereoselective organic synthesis","volume":"62","author":"Molander","year":"1990","journal-title":"Pure Appl. Chem."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"11406","DOI":"10.1021\/acs.chemrev.7b00167","article-title":"Catalytic Asymmetric Oxygenations with the Environmentally Benign Oxidants H2O2 and O2","volume":"117","author":"Bryliakov","year":"2017","journal-title":"Chem. Rev."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"14285","DOI":"10.1039\/C5CC05576H","article-title":"Biologically inspired non-heme iron-catalysts for asymmetric epoxidation; design principles and perspectives","volume":"51","author":"Ribas","year":"2015","journal-title":"Chem. Commun."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"931","DOI":"10.1016\/j.scitotenv.2017.04.184","article-title":"Synthesis of vegetable-oil based polymer by terpolymerization of epoxidized soybean oil, propylene oxide and carbon dioxide","volume":"598","author":"Shaarani","year":"2017","journal-title":"Sci. Total Environ."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"3629","DOI":"10.1039\/C9GC01337G","article-title":"Allylic oxidation of olefins with a manganese based metal\u2013organic framework","volume":"21","author":"Chen","year":"2019","journal-title":"Green Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"548","DOI":"10.3390\/pr8050548","article-title":"Green Pathway in Utilizing CO2 via Cycloaddition","volume":"8","author":"Kiatkittipong","year":"2020","journal-title":"Processes"},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"100935","DOI":"10.1016\/j.scp.2022.100935","article-title":"Vegetable oils as bio-based precursors for epoxies","volume":"31","author":"Marriam","year":"2023","journal-title":"Sustain. Chem. Pharm."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"903","DOI":"10.1039\/C4GC01307G","article-title":"One-step propylene formation from bio-glycerol over molybdena-based catalysts","volume":"17","author":"Zacharopoulou","year":"2015","journal-title":"Green Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"128","DOI":"10.1515\/pjct-2016-0059","article-title":"Technological aspects of vegetable oils epoxidation in the presence of ion exchange resins: A review","volume":"18","author":"Milchert","year":"2016","journal-title":"Pol. J. Chem. Technol."},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"747","DOI":"10.1039\/C8RE00094H","article-title":"Development of a selective, solvent-free epoxidation of limonene using hydrogen peroxide and a tungsten-based catalyst","volume":"3","author":"Resul","year":"2018","journal-title":"React. Chem. Eng."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1007\/s10924-019-01582-0","article-title":"Review: Bio-polyethylene from Wood Wastes","volume":"28","author":"Mendieta","year":"2020","journal-title":"J. Polym. Environ."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"S111","DOI":"10.1007\/s10947-007-0154-1","article-title":"Mechanism of olefin epoxidation with transition metal peroxo complexes: DFT study","volume":"48","author":"Yudanov","year":"2007","journal-title":"J. Struct. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"5191","DOI":"10.1021\/jo950930e","article-title":"Mechanism of Acid-Catalyzed Epoxidation of Alkenes with Peroxy Acids","volume":"62","author":"Bach","year":"1997","journal-title":"J. Org. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"9513","DOI":"10.1021\/ja981531e","article-title":"MCPBA Epoxidation of Alkenes:\u2009 Reinvestigation of Correlation between Rate and Ionization Potential","volume":"120","author":"Kim","year":"1998","journal-title":"J. Am. Chem. Soc."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"497","DOI":"10.1021\/ar030065h","article-title":"Ketone-Catalyzed Asymmetric Epoxidation Reactions","volume":"37","author":"Yang","year":"2004","journal-title":"Acc. Chem. Res."},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"117","DOI":"10.3390\/90300117","article-title":"Kinetics of the Epoxidation of Geraniol and Model Systems by Dimethyldioxirane","volume":"9","author":"Baumstark","year":"2004","journal-title":"Molecules"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"2847","DOI":"10.1021\/jo00216a007","article-title":"Dioxiranes: Synthesis and reactions of methyldioxiranes","volume":"50","author":"Murray","year":"1985","journal-title":"J. Org. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"2810","DOI":"10.1021\/jo980342b","article-title":"6-Oxo-1,1,4,4-tetramethyl-1,4-diazepinium Salts. A New Class of Catalysts for Efficient Epoxidation of Olefins with Oxone","volume":"63","author":"Denmark","year":"1998","journal-title":"J. Org. Chem."},{"key":"ref_22","doi-asserted-by":"crossref","unstructured":"Meng, Y., Taddeo, F., Aguilera, A.F., Cai, X., Russo, V., Tolvanen, P., and Leveneur, S. (2021). The Lord of the Chemical Rings: Catalytic Synthesis of Important Industrial Epoxide Compounds. Catalysts, 11.","DOI":"10.3390\/catal11070765"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1563","DOI":"10.1021\/cr0306945","article-title":"Chromium\u2212 and Manganese\u2212salen Promoted Epoxidation of Alkenes","volume":"105","author":"McGarrigle","year":"2005","journal-title":"Chem. Rev."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"7903","DOI":"10.1021\/jo034493c","article-title":"Factors Affecting the Catalytic Epoxidation of Olefins by Iron Porphyrin Complexes and H2O2 in Protic Solvents","volume":"68","author":"Nam","year":"2003","journal-title":"J. Org. Chem."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"57","DOI":"10.1016\/j.catcom.2008.07.033","article-title":"Homogeneous olefin epoxidation catalysed by an imidazolium-based manganese porphyrin","volume":"10","author":"Paula","year":"2008","journal-title":"Catal. Commun."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"132604","DOI":"10.1016\/j.tet.2021.132604","article-title":"Metal-porphyrin in epoxidation of olefins: Recent advances","volume":"104","author":"Ahmad","year":"2022","journal-title":"Tetrahedron"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"295","DOI":"10.1021\/ja00756a062","article-title":"Mechanism of epoxidation of olefins by covalent peroxides of molybdenum(VI)","volume":"94","author":"Sharpless","year":"1972","journal-title":"J. Am. Chem. Soc."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"1587","DOI":"10.1021\/jo00429a024","article-title":"Mechanism of the molybdenum and vanadium catalyzed epoxidation of olefins by alkyl hydroperoxides","volume":"42","author":"Chong","year":"1977","journal-title":"J. Org. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"5125","DOI":"10.1039\/C4DT03174A","article-title":"Vanadyl cationic complexes as catalysts in olefin oxidation","volume":"44","author":"Nunes","year":"2015","journal-title":"Dalton Trans."},{"key":"ref_30","doi-asserted-by":"crossref","unstructured":"Pisk, J., and Agustin, D. (2022). Molybdenum, Vanadium, and Tungsten-Based Catalysts for Sustainable (ep)Oxidation. Molecules, 27.","DOI":"10.3390\/molecules27186011"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"159","DOI":"10.1016\/0021-9517(91)90019-Z","article-title":"Synthesis of propylene oxide from propylene and hydrogen peroxide catalyzed by titanium silicalite","volume":"129","author":"Clerici","year":"1991","journal-title":"J. Catal."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"4125","DOI":"10.1016\/0040-4039(95)00675-3","article-title":"Hydrotalcite-promoted epoxidation of electron-deficient alkenes with hydrogen peroxide","volume":"36","author":"Cativiela","year":"1995","journal-title":"Tetrahedron Lett."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"75","DOI":"10.1016\/1381-1169(95)00229-4","article-title":"Selective catalytic synthesis of fine chemicals: Opportunities and trends","volume":"107","author":"Sheldon","year":"1996","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"1990","DOI":"10.1021\/ja00448a059","article-title":"Chiral hydroxamic acids as ligands in the vanadium catalyzed asymmetric epoxidation of allylic alcohols by tert-butyl hydroperoxide","volume":"99","author":"Michaelson","year":"1977","journal-title":"J. Am. Chem. Soc."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"76","DOI":"10.1016\/j.jcat.2005.05.026","article-title":"Mechanistic studies on metalloporphyrin epoxidation reactions with hydrogen peroxide: Evidence for two active oxidative species","volume":"234","author":"Rebelo","year":"2005","journal-title":"J. Catal."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"1275","DOI":"10.1246\/cl.1986.1275","article-title":"A New Iron (III) Porphyrin System for Olefin Epoxidation Catalysts","volume":"15","author":"Takagi","year":"1986","journal-title":"Chem. Lett."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"93","DOI":"10.1016\/j.ccr.2014.09.014","article-title":"Recent advances in enantioselective vanadium-catalyzed transformations","volume":"284","author":"Pellissier","year":"2015","journal-title":"Coord. Chem. Rev."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"361","DOI":"10.1021\/cs400959k","article-title":"Metal Organic Framework Catalysis: Quo vadis?","volume":"4","author":"Gascon","year":"2014","journal-title":"ACS Catal."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"4606","DOI":"10.1021\/cr9003924","article-title":"Engineering Metal Organic Frameworks for Heterogeneous Catalysis","volume":"110","author":"Corma","year":"2010","journal-title":"Chem. Rev."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"5578","DOI":"10.1039\/D2CC01137A","article-title":"Epoxidation vs. dehydrogenation of allylic alcohols: Heterogenization of the VO(acac)2 catalyst in a metal\u2013organic framework","volume":"58","author":"Negro","year":"2022","journal-title":"Chem. Commun."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"3310","DOI":"10.1021\/ja039436f","article-title":"Peroxovanadate Imidazole Complexes as Catalysts for Olefin Epoxidation:\u2009 Density Functional Study of Dynamics, 51V NMR Chemical Shifts, and Mechanism","volume":"126","author":"Schurhammer","year":"2004","journal-title":"J. Am. Chem. Soc."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1420","DOI":"10.1016\/j.ccr.2007.09.005","article-title":"Catalytic activities of Schiff base transition metal complexes","volume":"252","author":"Gupta","year":"2008","journal-title":"Coord. Chem. Rev."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"200","DOI":"10.1016\/j.ccr.2015.01.020","article-title":"Vanadium complexes: Recent progress in oxidation catalysis","volume":"301","author":"Sutradhar","year":"2015","journal-title":"Coord. Chem. Rev."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"415","DOI":"10.1016\/j.ica.2016.04.012","article-title":"Vanadium complexes supported on organic polymers as sustainable systems for catalytic oxidations","volume":"455","author":"Pessoa","year":"2017","journal-title":"Inorganica Chim. Acta"},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"2128","DOI":"10.1021\/acs.chemrev.8b00245","article-title":"Catalytic Applications of Vanadium: A Mechanistic Perspective","volume":"119","author":"Langeslay","year":"2019","journal-title":"Chem. Rev."},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"5357","DOI":"10.1016\/S0040-4020(02)00481-7","article-title":"Non-symmetrical tetradentate vanadyl Schiff base complexes derived from 1,2-phenylene diamine and 1,3-naphthalene diamine as catalysts for the oxidation of cyclohexene","volume":"58","author":"Boghaei","year":"2002","journal-title":"Tetrahedron"},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"749","DOI":"10.1007\/s11243-006-0062-9","article-title":"Effective oxidation of 1,2-cyclooctene by oxo-vanadium(IV) tetradentate Schiff base complexes under 1 atmosphere of molecular oxygen","volume":"31","author":"Mohebbi","year":"2006","journal-title":"Transit. Met. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"265","DOI":"10.1016\/j.molcata.2006.04.041","article-title":"Homogeneous green catalyst for epoxidation of cyclooctene by mono oxovanadium(IV) complexes of N2O2 donate ligand system","volume":"256","author":"Mohebbi","year":"2006","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"1336","DOI":"10.1016\/j.catcom.2006.11.021","article-title":"Catalytic oxidation of isosafrol by vanadium complexes","volume":"8","author":"Alvarez","year":"2007","journal-title":"Catal. Commun."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"190","DOI":"10.1016\/j.molcata.2006.01.058","article-title":"Oxovanadium(IV) based coordination polymers and their catalytic potentials for the oxidation of styrene, cyclohexene and trans-stilbene","volume":"250","author":"Maurya","year":"2006","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"9509","DOI":"10.1039\/C9RA01104H","article-title":"Redox activity of nickel and vanadium porphyrins: A possible mechanism behind petroleum genesis and maturation?","volume":"9","author":"Munoz","year":"2019","journal-title":"RSC Adv."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"1416","DOI":"10.1002\/asia.201000822","article-title":"A Vanadium Porphyrin with Temperature-Dependent Phase Transformation: Synthesis, Crystal Structures, Supramolecular Motifs and Properties","volume":"6","author":"Chen","year":"2011","journal-title":"Chem. Asian J."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"1421","DOI":"10.1039\/c39820001421","article-title":"Vanadium (II) porphyrin complexes: Synthesis and characterization. Crystal structure of 2,3,7,8,12,13,17,18-octaethylporphinatobis-(dimethylphenylphosphine)vanadium(II)","volume":"24","author":"Poncet","year":"1982","journal-title":"J. Chem. Soc. Chem. Commun."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1002\/cjoc.202100576","article-title":"Oxygen Atom Transfer Mechanism for Vanadium-Oxo Porphyrin Complexes Mediated Aerobic Olefin Epoxidation","volume":"40","author":"Liu","year":"2022","journal-title":"Chin. J. Chem."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"7520","DOI":"10.1002\/anie.200802523","article-title":"Vanadium-Catalyzed Enantioselective Desymmetrization of meso Secondary Allylic Alcohols and Homoallylic Alcohols","volume":"47","author":"Li","year":"2008","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"2281","DOI":"10.1016\/j.ccr.2011.04.001","article-title":"Aerobic oxidation of organic compounds catalyzed by vanadium compounds","volume":"255","author":"Kirihara","year":"2011","journal-title":"Coord. Chem. Rev."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"2165","DOI":"10.1016\/j.ccr.2011.03.006","article-title":"Mechanistic aspects of vanadium catalysed oxidations with peroxides","volume":"255","author":"Conte","year":"2011","journal-title":"Coord. Chem. Rev."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"1","DOI":"10.1016\/j.jcat.2012.06.002","article-title":"Mechanistic insight into the cyclohexene epoxidation with VO(acac)2 and tert-butyl hydroperoxide","volume":"294","author":"Vandichel","year":"2012","journal-title":"J. Catal."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"116","DOI":"10.1016\/j.ica.2016.12.018","article-title":"Epoxidation of alkenes by an oxidovanadium(IV) tetradentate Schiff base complex as an efficient catalyst with tert-butyl hydroperoxide","volume":"457","author":"Sedighipoor","year":"2017","journal-title":"Inorganica Chim. Acta"},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"140","DOI":"10.1016\/j.jcat.2009.08.006","article-title":"Mechanism of oxidations with H2O2 catalyzed by vanadate anion or oxovanadium(V) triethanolaminate (vanadatrane) in combination with pyrazine-2-carboxylic acid (PCA): Kinetic and DFT studies","volume":"267","author":"Kirillova","year":"2009","journal-title":"J. Catal."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"5460","DOI":"10.1039\/b902424g","article-title":"Epoxidation of olefins catalysed by vanadium\u2013salan complexes: A theoretical mechanistic study","volume":"28","author":"Kuznetsov","year":"2009","journal-title":"Dalton Trans."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"95","DOI":"10.2174\/157019309788167738","article-title":"Hydrocarbon Oxygenations with Peroxides Catalyzed by Metal Compounds","volume":"6","year":"2009","journal-title":"Mini-Rev. Org. Chem."},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"135","DOI":"10.1007\/s10562-008-9406-8","article-title":"Oxidation of saturated hydrocarbons to alkyl hydroperoxides by a \u2018H2O2\/titanosilicalite-1\/NaOH\/MeCN\u2019 system","volume":"123","author":"Kirillova","year":"2008","journal-title":"Catal. Lett."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"157","DOI":"10.1016\/j.cattod.2011.07.007","article-title":"Oxidative functional group transformations with hydrogen peroxide catalyzed by a divanadium-substituted phosphotungstate","volume":"185","author":"Mizuno","year":"2012","journal-title":"Catal. Today"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"7549","DOI":"10.1002\/chem.201101001","article-title":"Efficient Epoxidation of Electron-Deficient Alkenes with Hydrogen Peroxide Catalyzed by [\u03b3-PW10O38V2(\u03bc-OH)2]3\u2212","volume":"17","author":"Kamata","year":"2011","journal-title":"Chem. A Eur. J."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"56","DOI":"10.1016\/j.cattod.2012.01.024","article-title":"Insights on the mechanistic features of catalytic oxidations of simple and conjugated olefins promoted by VO(acac)2\/H2O2 system, in acetonitrile: A computational study","volume":"192","author":"Aschi","year":"2012","journal-title":"Catal. Today"},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"785","DOI":"10.1103\/PhysRevB.37.785","article-title":"Development of the Colle-Salvetti correlation-energy formula into a functional of the electron density","volume":"37","author":"Lee","year":"1988","journal-title":"Phys. Rev. B"},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"211","DOI":"10.1016\/j.apcata.2010.02.022","article-title":"Synthesis and characterization of novel oxovanadium(IV) complexes with 4-acyl-5-pyrazolone donor ligands: Evaluation of their catalytic activity for the oxidation of styrene derivatives","volume":"378","author":"Marchetti","year":"2010","journal-title":"Appl. Catal. A Gen."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"6337","DOI":"10.1002\/anie.201005742","article-title":"Synthesis of 2-Keto-anti-1,3-diols by Chemoselective Tandem Oxidation of 2-B(pin)-Substituted Allylic Alcohols","volume":"50","author":"Hussain","year":"2011","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"1231","DOI":"10.1039\/C3CC47921H","article-title":"Dearomatization of tryptophols via a vanadium-catalyzed asymmetric epoxidation and ring-opening cascade","volume":"50","author":"Han","year":"2014","journal-title":"Chem. Commun."},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"3203","DOI":"10.1021\/acs.joc.5b00185","article-title":"Asymmetric Epoxidation of Allylic Alcohols Catalyzed by Vanadium\u2013Binaphthylbishydroxamic Acid Complex","volume":"80","author":"Noji","year":"2015","journal-title":"J. Org. Chem."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"5321","DOI":"10.1016\/j.tet.2014.05.011","article-title":"Formation of 3-acyloxy-\u03b3-butyrolactones from 4-pentenols in vanadium-catalyzed oxidations","volume":"70","author":"Amberg","year":"2014","journal-title":"Tetrahedron"},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"120","DOI":"10.1016\/j.ica.2014.02.007","article-title":"cis-2,6-Bis-(methanolate)-piperidine oxovanadium(V) complexes as catalysts for oxidative alkenol cyclization by tert-butyl hydroperoxide","volume":"420","author":"Amberg","year":"2014","journal-title":"Inorganica Chim. Acta"},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1016\/j.inoche.2011.12.044","article-title":"Synthesis, characterization and crystal structure determination of a new oxovanadium(IV) Schiff base complex: The catalytic activity in the epoxidation of cyclooctene","volume":"18","author":"Grivani","year":"2012","journal-title":"Inorg. Chem. Commun."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"779","DOI":"10.1016\/j.cclet.2015.03.014","article-title":"A new oxidovanadium(IV) Schiff base complex containing asymmetric tetradentate ONN\u2032O\u2032 Schiff base ligand: Synthesis, characterization, crystal structure determination, thermal study and catalytic activity","volume":"26","author":"Grivani","year":"2015","journal-title":"Chin. Chem. Lett."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"265","DOI":"10.1016\/j.poly.2011.09.011","article-title":"Synthesis, characterization and crystal structures of new bidentate Schiff base ligand and its vanadium(IV) complex: The catalytic activity of vanadyl complex in epoxidation of alkenes","volume":"31","author":"Grivani","year":"2012","journal-title":"Polyhedron"},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"556","DOI":"10.1080\/24701556.2021.1897618","article-title":"Synthesis, crystal structures and catalytic activity of oxidovanadium(V) complexes with tridentate ONO aroylhydrazone ligands","volume":"52","author":"Liang","year":"2022","journal-title":"Inorg. Nano-Met. Chem."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"441","DOI":"10.17344\/acsi.2020.6553","article-title":"Synthesis, X-Ray Crystal Structures and Catalytic Epoxidation of Oxidovanadium(V) Complexes with Aroylhydrazone and Ethyl Maltolate Ligands","volume":"68","author":"Zou","year":"2021","journal-title":"Acta Chim. Slov."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"29","DOI":"10.1016\/j.catcom.2008.07.035","article-title":"Oxidation of anethole with hydrogen peroxide catalyzed by oxovanadium aromatic carboxylate complexes","volume":"10","author":"Xiao","year":"2008","journal-title":"Catal. Commun."},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"1337","DOI":"10.1016\/j.tetasy.2011.07.011","article-title":"An efficient enantioselective synthesis of florfenicol via a vanadium-catalyzed asymmetric epoxidation","volume":"22","author":"Li","year":"2011","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_81","unstructured":"McNaught, A.D., and Wilkinson, A. (1997). Compendium of Chemical Terminology, (the \u201cGold Book\u201d), Blackwell Scientific Publications. [2nd ed.]. Online version (2019-) created by S. J. Chalk."},{"key":"ref_82","doi-asserted-by":"crossref","first-page":"0942","DOI":"10.1055\/s-2002-31894","article-title":"VO(acac)2\/TBHP Catalyzed Epoxidation of 2-(2-Alkenyl)phenols. Highly Regio- and Diastereoselective Oxidative Cyclization to 2,3-Dihydro-benzofuranols and 3-Chromanols","volume":"2002","author":"Lattanzi","year":"2002","journal-title":"Synlett"},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"4037","DOI":"10.1016\/j.tet.2004.03.010","article-title":"A new approach to 2,2-disubstituted chromenes and tetrahydroquinolines through intramolecular cyclization of chiral 3,4-epoxy alcohols","volume":"60","author":"Goujon","year":"2004","journal-title":"Tetrahedron"},{"key":"ref_84","doi-asserted-by":"crossref","first-page":"2625","DOI":"10.1016\/S0957-4166(02)00741-3","article-title":"Asymmetric epoxidation of allylic alcohols catalyzed by new chiral vanadium(V) complexes","volume":"13","author":"Wu","year":"2002","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"3194","DOI":"10.1039\/b505324b","article-title":"Amino acid-derived hydroxamic acids as chiral ligands in the vanadium catalysed epoxidation","volume":"3","author":"Malkov","year":"2005","journal-title":"Org. Biomol. Chem."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"286","DOI":"10.1021\/ja067495y","article-title":"Vanadium-Catalyzed Asymmetric Epoxidation of Homoallylic Alcohols","volume":"129","author":"Zhang","year":"2007","journal-title":"J. Am. Chem. Soc."},{"key":"ref_87","doi-asserted-by":"crossref","first-page":"3350","DOI":"10.1021\/jo900294h","article-title":"Vanadium-Catalyzed Asymmetric Epoxidation of Allylic Alcohols in Water","volume":"74","author":"Malkov","year":"2009","journal-title":"J. Org. Chem."},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"4592","DOI":"10.1039\/b509436d","article-title":"Ligand-accelerated vanadium-catalysed epoxidation in water","volume":"36","author":"Bourhani","year":"2005","journal-title":"Chem. Commun."},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"1355","DOI":"10.1016\/S0957-4166(03)00213-1","article-title":"Control of enantioselectivity through a hydrogen-bonded template in the vanadium(V)-catalyzed epoxidation of allylic alcohols by optically active hydroperoxides","volume":"14","author":"Adam","year":"2003","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"1669","DOI":"10.1002\/ejoc.200400736","article-title":"Vanadium-Catalyzed Asymmetric Epoxidation of Allylic Alcohols Mediated by (+)-Norcamphor-Derived Hydroperoxide","volume":"2005","author":"Lattanzi","year":"2005","journal-title":"Eur. J. Org. Chem."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"5923","DOI":"10.1016\/j.tetlet.2006.06.051","article-title":"Tuning the oxidation properties of vanadium(V) through ligand stoichiometry","volume":"47","author":"Zeng","year":"2006","journal-title":"Tetrahedron Lett."},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"609","DOI":"10.1039\/b208748k","article-title":"Multinuclear NMR study of the reactive intermediates in enantioselective epoxidations of allylic alcohols catalyzed by a vanadium complex derived from a planar-chiral hydroxamic acid","volume":"27","author":"Bryliakov","year":"2003","journal-title":"New J. Chem."},{"key":"ref_93","doi-asserted-by":"crossref","first-page":"98","DOI":"10.1007\/s10562-010-0281-8","article-title":"Oxidovanadium(IV) Complexes of 3-Hydroxy-4-pyrone and 3-Hydroxy-4-pyridinone Ligands: A New Generation of Homogeneous Catalysts for the Epoxidation of Geraniol","volume":"135","author":"Pereira","year":"2010","journal-title":"Catal. Lett."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"2232","DOI":"10.1016\/j.ccr.2011.05.009","article-title":"Oxovanadium complexes in catalytic oxidations","volume":"255","author":"Pombeiro","year":"2011","journal-title":"Coord. Chem. Rev."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"67","DOI":"10.1016\/j.micromeso.2012.03.041","article-title":"Oxidovanadium(IV) acetylacetonate immobilized onto CMK-3 for heterogeneous epoxidation of geraniol","volume":"160","author":"Dorbes","year":"2012","journal-title":"Microporous Mesoporous Mater."},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"4582","DOI":"10.1002\/ejic.200500435","article-title":"Anchoring of Vanadyl Acetylacetonate onto Amine-Functionalised Activated Carbons: Catalytic Activity in the Epoxidation of an Allylic Alcohol","volume":"2005","author":"Jarrais","year":"2005","journal-title":"Eur. J. Inorg. Chem."},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"9171","DOI":"10.1002\/anie.201103713","article-title":"Highly Enantioselective and Efficient Asymmetric Epoxidation Catalysts: Inorganic Nanosheets Modified with \u03b1-Amino Acids as Ligands","volume":"50","author":"Wang","year":"2011","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_98","doi-asserted-by":"crossref","first-page":"70","DOI":"10.1016\/j.jcat.2012.11.022","article-title":"Multilple host\u2013guest interactions in heterogeneous vanadium catalysts: Inorganic nanosheets modified alpha-amino acids as ligands","volume":"298","author":"Liu","year":"2013","journal-title":"J. Catal."},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"12350","DOI":"10.1002\/chem.201301150","article-title":"Validity of Inorganic Nanosheets as an Efficient Planar Substituent To Enhance the Enantioselectivity of Transition-Metal-Catalyzed Asymmetric Synthesis","volume":"19","author":"Zhao","year":"2013","journal-title":"Chem. A Eur. J."},{"key":"ref_100","doi-asserted-by":"crossref","first-page":"9911","DOI":"10.1002\/chem.201201659","article-title":"Nanosheet-Enhanced Enantioselectivity in the Vanadium-Catalyzed Asymmetric Epoxidation of Allylic Alcohols","volume":"18","author":"Zhao","year":"2012","journal-title":"Chem. A Eur. J."},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"8322","DOI":"10.1021\/acs.orglett.2c03305","article-title":"Directed Diastereoselective Cyclopropanation and Epoxidation of Alkenyl Cyclopropyl Carbinol Derivatives","volume":"24","author":"Cohen","year":"2022","journal-title":"Org. Lett."},{"key":"ref_102","doi-asserted-by":"crossref","first-page":"131","DOI":"10.1002\/anie.199301313","article-title":"Sequential Transformations in Organic Chemistry: A Synthetic Strategy with a Future","volume":"32","author":"Tietze","year":"1993","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_103","doi-asserted-by":"crossref","first-page":"115","DOI":"10.1021\/cr950027e","article-title":"Domino Reactions in Organic Synthesis","volume":"96","author":"Tietze","year":"1996","journal-title":"Chem. Rev."},{"key":"ref_104","doi-asserted-by":"crossref","first-page":"693","DOI":"10.1016\/j.tetasy.2007.03.002","article-title":"Organocatalytic enantioselective multicomponent reactions (OEMCRs)","volume":"18","author":"Guillena","year":"2007","journal-title":"Tetrahedron Asymmetry"},{"key":"ref_105","doi-asserted-by":"crossref","first-page":"442","DOI":"10.1021\/cr300271k","article-title":"Stereocontrolled Domino Reactions","volume":"113","author":"Pellissier","year":"2013","journal-title":"Chem. Rev."},{"key":"ref_106","doi-asserted-by":"crossref","first-page":"3347","DOI":"10.1002\/adsc.201200254","article-title":"Recent Developments in Enantioselective Metal-Catalyzed Domino Reactions","volume":"354","author":"Clavier","year":"2012","journal-title":"Adv. Synth. Catal."},{"key":"ref_107","doi-asserted-by":"crossref","first-page":"1619","DOI":"10.1016\/j.tet.2005.10.040","article-title":"Asymmetric domino reactions. Part A: Reactions based on the use of chiral auxiliaries","volume":"62","author":"Pellissier","year":"2006","journal-title":"Tetrahedron"},{"key":"ref_108","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1016\/S1381-1169(01)00330-2","article-title":"Synthesis, characterization and study of vanadyl tetradentate Schiff base complexes as catalyst in aerobic selective oxidation of olefins","volume":"179","author":"Boghaei","year":"2002","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_109","doi-asserted-by":"crossref","first-page":"789","DOI":"10.3390\/catal12070789","article-title":"Mechanistic Details of the Sharpless Epoxidation of Allylic Alcohols&mdash; A Combined URVA and Local Mode Study","volume":"12","author":"Freindorf","year":"2022","journal-title":"Catalysts"},{"key":"ref_110","doi-asserted-by":"crossref","first-page":"263","DOI":"10.1016\/j.apcata.2004.10.005","article-title":"Oxovanadium(IV) complexes as homogeneous catalyst\u2014Aerobic epoxidation of olefins","volume":"278","author":"Mohebbi","year":"2005","journal-title":"Appl. Catal. A Gen."},{"key":"ref_111","doi-asserted-by":"crossref","first-page":"132888","DOI":"10.1016\/j.molstruc.2022.132888","article-title":"Structural investigations and catalytic performances of a new oxovanadium complex derived from 1,2-bis((E)-5-bromo-2-hydroxybenzylideneamino)-4-methylbenzene","volume":"1261","author":"Dekar","year":"2022","journal-title":"J. Mol. Struct."},{"key":"ref_112","doi-asserted-by":"crossref","first-page":"104192","DOI":"10.1016\/j.jtice.2021.104192","article-title":"Nickel (II), copper (II), and vanadyl (II) complexes with tridentate nicotinoyl hydrazone derivative functionalized as effective catalysts for epoxidation processes and as biological reagents","volume":"132","author":"Adam","year":"2022","journal-title":"J. Taiwan Inst. Chem. Eng."},{"key":"ref_113","doi-asserted-by":"crossref","first-page":"115268","DOI":"10.1016\/j.poly.2021.115268","article-title":"Substituent effects in dioxovanadium(V) schiff-base complexes: Tuning the outcomes of oxidation reactions","volume":"205","author":"McCaffrey","year":"2021","journal-title":"Polyhedron"},{"key":"ref_114","doi-asserted-by":"crossref","first-page":"65","DOI":"10.1016\/j.apcata.2008.05.016","article-title":"Oxovanadium(IV) Schiff base complexes derived from 2,2\u2032-dimethylpropandiamine: A homogeneous catalyst for cyclooctene and styrene oxidation","volume":"346","author":"Rayati","year":"2008","journal-title":"Appl. Catal. A Gen."},{"key":"ref_115","doi-asserted-by":"crossref","first-page":"1545","DOI":"10.1016\/j.inoche.2007.09.023","article-title":"A new di-\u03bc-oxo bis[oxovanadium(V)] complex containing Schiff base ligand derived from 1,2-diaminopropane and 2\u2032-hydroxy-4\u2032-methoxyacetophenone: Synthesis, structure and catalytic properties","volume":"10","author":"Rayati","year":"2007","journal-title":"Inorg. Chem. Commun."},{"key":"ref_116","doi-asserted-by":"crossref","first-page":"1722","DOI":"10.1016\/j.jorganchem.2010.04.020","article-title":"A new single pot synthesis of \u03bc-bis(oxido)bis{oxidovanadium(V)} dipicolinato complex with 2-aminopyridinium as counter cation: Spectroscopic, structural, catalytic and theoretical studies","volume":"695","author":"Trivedi","year":"2010","journal-title":"J. Organomet. Chem."},{"key":"ref_117","doi-asserted-by":"crossref","first-page":"4634","DOI":"10.1039\/D1NJ06015E","article-title":"Oxo(corrolato)vanadium(iv) catalyzed epoxidation: Oxo(peroxo)(corrolato)vanadium(v) is the true catalytic species","volume":"46","author":"Nayak","year":"2022","journal-title":"New J. Chem."},{"key":"ref_118","doi-asserted-by":"crossref","first-page":"1041","DOI":"10.1016\/S0013-4686(02)00819-8","article-title":"Paired electrosynthesis of epoxides and dibromides from olefinic compounds","volume":"48","author":"Shen","year":"2003","journal-title":"Electrochim. Acta"},{"key":"ref_119","first-page":"69","article-title":"Complexes of glutathione with heavy metals as catalysts for oxidation","volume":"99","author":"Dimitrova","year":"2010","journal-title":"React. Kinet. Mech. Catal."},{"key":"ref_120","doi-asserted-by":"crossref","first-page":"3542","DOI":"10.1021\/ic8017985","article-title":"Synthesis, Characterization, and Application of Vanadium\u2212Salan Complexes in Oxygen Transfer Reactions","volume":"48","author":"Henriques","year":"2009","journal-title":"Inorg. Chem."},{"key":"ref_121","doi-asserted-by":"crossref","first-page":"120813","DOI":"10.1016\/j.ica.2022.120813","article-title":"Synthesis, structure and catalytic activity of new oxovanadium(V) complexes with deferiprone and N,N-donor ligands","volume":"534","author":"Sultana","year":"2022","journal-title":"Inorganica Chim. Acta"},{"key":"ref_122","doi-asserted-by":"crossref","first-page":"669","DOI":"10.1007\/s11243-011-9517-8","article-title":"Binuclear vanadium(V) complexes of bis(aryl)adipohydrazone: Synthesis, spectroscopic studies, crystal structure and catalytic activity","volume":"36","author":"Noei","year":"2011","journal-title":"Transit. Met. Chem."},{"key":"ref_123","doi-asserted-by":"crossref","first-page":"477","DOI":"10.1007\/s13738-014-0505-8","article-title":"Epoxidation of alkenes and oxidation of sulfides catalyzed by a new binuclear vanadium bis-oxazoline complex","volume":"12","author":"Javadi","year":"2015","journal-title":"J. Iran. Chem. Soc."},{"key":"ref_124","doi-asserted-by":"crossref","first-page":"52","DOI":"10.1016\/j.molcata.2015.03.016","article-title":"Pyridoxal based ONS and ONO vanadium(V) complexes: Structural analysis and catalytic application in organic solvent free epoxidation","volume":"403","author":"Pisk","year":"2015","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_125","doi-asserted-by":"crossref","first-page":"267","DOI":"10.1007\/s11243-012-9687-z","article-title":"Synthesis, structure and catalytic activity of an oxo-bridged dinuclear oxovanadium complex of an isonicotinohydrazide ligand","volume":"38","author":"Farrokhi","year":"2013","journal-title":"Transit. Met. Chem."},{"key":"ref_126","doi-asserted-by":"crossref","first-page":"144","DOI":"10.1016\/j.ica.2010.09.021","article-title":"Oxo-bridged bis oxo-vanadium(V) complexes with tridentate Schiff base ligands (VOL)2O (L = SAE, SAMP, SAP): Synthesis, structure and epoxidation catalysis under solvent-free conditions","volume":"364","author":"Cordelle","year":"2010","journal-title":"Inorganica Chim. Acta"},{"key":"ref_127","doi-asserted-by":"crossref","first-page":"78","DOI":"10.1016\/j.ica.2016.07.058","article-title":"Catalytic oxidation of olefins and sulfides in the presence of hydrazone-oxidovanadium(V) complex containing VOCl2+ core","volume":"453","author":"Bikas","year":"2016","journal-title":"Inorganica Chim. Acta"},{"key":"ref_128","doi-asserted-by":"crossref","first-page":"15","DOI":"10.1016\/j.ica.2016.10.005","article-title":"Dioxidovanadium(V) complexes containing thiazol-hydrazone NNN-donor ligands and their catalytic activity in the oxidation of olefins","volume":"455","author":"Ghorbanloo","year":"2017","journal-title":"Inorganica Chim. Acta"},{"key":"ref_129","doi-asserted-by":"crossref","first-page":"123","DOI":"10.1016\/j.poly.2016.09.060","article-title":"Synthesis, crystal structures of oxovanadium(V) complexes with hydrazone ligands and their catalytic performance for the styrene oxidation","volume":"121","author":"Zhang","year":"2017","journal-title":"Polyhedron"},{"key":"ref_130","doi-asserted-by":"crossref","first-page":"6968","DOI":"10.1039\/c1dt10261c","article-title":"Synthesis, characterization, reactivity and catalytic activity of oxidovanadium(iv), oxidovanadium(v) and dioxidovanadium(v) complexes of benzimidazole modified ligands","volume":"40","author":"Maurya","year":"2011","journal-title":"Dalton Trans."},{"key":"ref_131","doi-asserted-by":"crossref","first-page":"258","DOI":"10.1016\/j.molstruc.2016.11.059","article-title":"Synthesis, characterization, EPR spectroscopy and catalytic activity of a new oxidovanadium(IV) complex with N2O2-donor ligand","volume":"1131","author":"Bikas","year":"2017","journal-title":"J. Mol. Struct."},{"key":"ref_132","first-page":"1351","article-title":"Oxidations by the reagent \u201cO2\u2013H2O2\u2013vanadium derivative\u2013pyrazine-2-carboxylic acid\u201d. Part 12.1 Main features, kinetics and mechanism of alkane hydroperoxidation","volume":"2","author":"Kozlov","year":"2001","journal-title":"J. Chem. Soc. Perkin Trans."}],"container-title":["International Journal of Molecular Sciences"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1422-0067\/24\/15\/12299\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T20:23:42Z","timestamp":1760127822000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1422-0067\/24\/15\/12299"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2023,8,1]]},"references-count":132,"journal-issue":{"issue":"15","published-online":{"date-parts":[[2023,8]]}},"alternative-id":["ijms241512299"],"URL":"https:\/\/doi.org\/10.3390\/ijms241512299","relation":{},"ISSN":["1422-0067"],"issn-type":[{"value":"1422-0067","type":"electronic"}],"subject":[],"published":{"date-parts":[[2023,8,1]]}}}