{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,1]],"date-time":"2026-10-01T03:53:15Z","timestamp":1790826795301,"version":"4.1.0"},"reference-count":42,"publisher":"MDPI AG","issue":"9","license":[{"start":{"date-parts":[[2022,4,28]],"date-time":"2022-04-28T00:00:00Z","timestamp":1651104000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>In this paper we describe a detailed mechanistic studies on the [FeII(PBO)2(CF3SO3)2] (1), [FeII(PBT)2(CF3SO3)2] (2), and [FeII(PBI)3](CF3SO3)2 (3)-catalyzed (PBO = 2-(2\u2032-pyridyl)benzoxazole, PBT = 2-(2\u2032-pyridyl)benzthiazole, PBI = 2-(2\u2032-pyridyl)benzimidazole) Baeyer\u2013Villiger oxidation of cycloketones by dioxygen with cooxidation of aldehydes and peroxycarboxylic acids, including the kinetics on the reactivity of (\u03bc-1,2-peroxo)diiron(III), acylperoxo- and iodosylbenzene-iron(III) species as key intermediates.<\/jats:p>","DOI":"10.3390\/molecules27092814","type":"journal-article","created":{"date-parts":[[2022,4,28]],"date-time":"2022-04-28T22:20:06Z","timestamp":1651184406000},"page":"2814","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":11,"title":["Catalytic and Stoichiometric Baeyer\u2013Villiger Oxidation Mediated by Nonheme Peroxo-Diiron(III), Acylperoxo, and Iodosylbenzene Iron(III) Intermediates"],"prefix":"10.3390","volume":"27","author":[{"given":"D\u00f3ra","family":"Lakk-Bog\u00e1th","sequence":"first","affiliation":[{"name":"Research Group of Bioorganic and Biocoordination Chemistry, Faculty of Engineering, Center for Natural Sciences, University of Pannonia, H-8201 Veszpr\u00e9m, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Mikl\u00f3s Istv\u00e1n","family":"Sz\u00e1vuly","sequence":"additional","affiliation":[{"name":"Research Group of Bioorganic and Biocoordination Chemistry, Faculty of Engineering, Center for Natural Sciences, University of Pannonia, H-8201 Veszpr\u00e9m, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Patrik","family":"T\u00f6r\u00f6k","sequence":"additional","affiliation":[{"name":"Research Group of Bioorganic and Biocoordination Chemistry, Faculty of Engineering, Center for Natural Sciences, University of Pannonia, H-8201 Veszpr\u00e9m, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-1427-8105","authenticated-orcid":false,"given":"J\u00f3zsef","family":"Kaizer","sequence":"additional","affiliation":[{"name":"Research Group of Bioorganic and Biocoordination Chemistry, Faculty of Engineering, Center for Natural Sciences, University of Pannonia, H-8201 Veszpr\u00e9m, Hungary"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2022,4,28]]},"reference":[{"key":"ref_1","first-page":"251","article-title":"The Baeyer-Villiger Oxidation of Ketones and Aldehydes","volume":"43","author":"Krow","year":"1993","journal-title":"Org. React."},{"key":"ref_2","first-page":"73","article-title":"Baeyer-Villiger Oxidation of Ketones and Aldehydes","volume":"9","author":"Hassal","year":"1957","journal-title":"Org. React."},{"key":"ref_3","doi-asserted-by":"crossref","first-page":"1151","DOI":"10.1055\/s-1997-977","article-title":"Enantioselective metal-catalyzed Baeyer-Villiger oxidation of cyclobutanones","volume":"10","author":"Bolm","year":"1997","journal-title":"Synlett."},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"33","DOI":"10.1023\/A:1013877131474","article-title":"Lewis acid behavior of cationic complexes of palladium (II) and platinum (II): Some examples of catalytic applications","volume":"19","author":"Strucul","year":"2002","journal-title":"Top. Catal."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"737","DOI":"10.1002\/(SICI)1099-0690(199904)1999:4<737::AID-EJOC737>3.0.CO;2-B","article-title":"100 years of Baeyer\u2013Villiger oxidations","volume":"1999","author":"Renz","year":"1999","journal-title":"Eur. J. Org. Chem."},{"key":"ref_6","doi-asserted-by":"crossref","first-page":"1198","DOI":"10.1002\/(SICI)1521-3773(19980518)37:9<1198::AID-ANIE1198>3.0.CO;2-Y","article-title":"Transition metal catalysis in the Baeyer\u2013Villiger oxidation of ketones","volume":"37","author":"Strukul","year":"1998","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"7557","DOI":"10.1016\/S0040-4039(00)60823-7","article-title":"Fe2O3-catalyzed baeyer-villiger oxidation of ketones with molecular oxygen in the presence of aldehydes","volume":"33","author":"Murahashi","year":"1992","journal-title":"Tetrahedron Lett."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"135","DOI":"10.1016\/1381-1169(95)00055-0","article-title":"Catalysis of transition metal-functionalized hydrotalcites for the Baeyer-Villiger oxidation of ketones in the presence of molecular oxygen and benzaldehyde","volume":"102","author":"Kaneda","year":"1995","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"2973","DOI":"10.1002\/1521-3765(20010716)7:14<2972::AID-CHEM2972>3.0.CO;2-Z","article-title":"Solvent-free routes to clean technology","volume":"7","author":"Thomas","year":"2001","journal-title":"Chem. Eur. J."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Bolm, C., Palazzi, C., Francio, G., and Leitner, W. (2002). Baeyer\u2013Villiger oxidation in compressed CO2. Chem. Commun., 1588\u20131589.","DOI":"10.1039\/b202727e"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"138","DOI":"10.1016\/j.cej.2013.12.027","article-title":"Biomimetic Baeyer\u2013Villiger oxidation of ketones with SnO2 as cocatalyst, features in activating carbonyl group of substrates","volume":"241","author":"Chen","year":"2014","journal-title":"Chem. Eng. J."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"779","DOI":"10.1002\/cctc.201501107","article-title":"Fabrication of Fe3O4-l-dopa-CuII\/SnIV@Micro-Mesoporous-SiO2 Catalyst Applied to Baeyer\u2013Villiger Oxidation Reaction","volume":"8","author":"Huo","year":"2016","journal-title":"ChemCatChem"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"13364","DOI":"10.1039\/C7DT02534C","article-title":"Flexibility and lability of a phenyl ligand in hetero-organometallic 3d metal\u2013Sn(iv) compounds and their catalytic activity in Baeyer\u2013Villiger oxidation of cyclohexanone","volume":"46","author":"Hazra","year":"2017","journal-title":"Dalton Trans."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"2443","DOI":"10.1002\/anie.199524431","article-title":"Synthetic Aspects of Metal-Catalyzed Oxidations of Amines and Related Reactions","volume":"34","author":"Murahashi","year":"1995","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"3405","DOI":"10.1016\/S0040-4039(00)79167-2","article-title":"Use of molecular oxygen in the Baeyer-Villiger oxidation the influence of metal catalysts","volume":"34","author":"Bolm","year":"1993","journal-title":"Tetrahedron Lett."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"295","DOI":"10.1007\/s11144-016-1094-6","article-title":"Ordered mesoporous Sn\u2013TiO2catalysts via an evaporation induced self-assembly method for the Baeyer\u2013Villiger oxidation of cyclohexanone by molecular oxygen","volume":"120","author":"Zhou","year":"2017","journal-title":"React. Kinet. Mech. Catal."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"191","DOI":"10.1016\/j.cattod.2015.07.051","article-title":"Insight into the cocatalyst effect of 4A molecular sieve on Sn (II) porphyrin-catalyzed B\u2013V oxidation of cyclohexanone","volume":"264","author":"Chen","year":"2016","journal-title":"Catal. Today"},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"2915","DOI":"10.1021\/jo00090a001","article-title":"Baeyer-Villiger oxidation of ketones using molecular oxygen and benzaldehyde in the absence of metal catalysts","volume":"59","author":"Kaneda","year":"1994","journal-title":"J. Org. Chem."},{"key":"ref_19","doi-asserted-by":"crossref","unstructured":"Karcz, R., Napruszewska, B.D., Michalik, A., Krysciak-Czerwenka, J., Duraczynska, D., and Serwicka, E.M. (2021). Fine Crystalline Mg-Al Hydrotalcites as Catalysts for Baeyer-Villiger Oxidation of Cyclohexanone with H2O2. Catalysts, 11.","DOI":"10.3390\/catal11121493"},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"81","DOI":"10.1039\/a708975i","article-title":"Room temperature Baeyer-Villiger oxidation of cycllic and linear ketones using molecular oxygen, catalysed by a novel silica-supported nickel complex","volume":"22","author":"Chisem","year":"1998","journal-title":"New J. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","unstructured":"Raja, R., Thomas, J.M., and Sankar, G. (1999). Baeyer\u2013Villiger oxidations with a difference: Molecular sieve redox catalysts for the low-temperature conversion of ketones to lactones. Chem. Commun., 525\u2013526.","DOI":"10.1039\/a900080a"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"99","DOI":"10.1016\/j.molcata.2005.03.027","article-title":"Iron-containing MCM41 catalysts for Baeyer-Villiger oxidation of ketones using molecular oxygen and benzaldehyde","volume":"236","author":"Kawabata","year":"2005","journal-title":"J. Mol. Catal. A"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"279","DOI":"10.1016\/j.molcata.2006.03.077","article-title":"Improved Fe\/Mg-Al hydrotalcite catalyst for Baeyer\u2013Villiger oxidation of ketones with molecular oxygen and benzaldehyde","volume":"253","author":"Kawabata","year":"2006","journal-title":"J. Mol. Catal. A Chem."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"48","DOI":"10.1016\/j.catcom.2018.01.014","article-title":"Effect of MgAl hydrotalcite crystallinity on catalytic Baeyer-Villiger oxidation of cyclohexanone with H2O2\/acetonitrile","volume":"107","author":"Karcz","year":"2018","journal-title":"Catal. Comm."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"94","DOI":"10.1142\/S1088424608000121","article-title":"Baeyer-Villiger oxidation of ketones catalyzed by iron(III) meso-tetraphenylporphyrin chloride in the presence of molecular oxygen","volume":"12","author":"Zhou","year":"2008","journal-title":"J. Porphyr. Phthalocyanines"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"4241","DOI":"10.1016\/j.tet.2013.03.088","article-title":"Remarkable differences between benzaldehyde and isobutyraldehyde as coreductant in the performance toward the iron(III) porphyrins-catalyzed aerobic Baeyer\u2013Villiger oxidation of cyclohexanone, kinetic and mechanistic features","volume":"69","author":"Lan","year":"2013","journal-title":"Tetrahedron"},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"2397","DOI":"10.1105\/tpc.105.033738","article-title":"Arabidopsis CYP85A2, a cytochrome P450, mediates the Baeyer-Villiger oxidation of castasterone to brassinolide in brassinosteroid biosynthesis","volume":"8","author":"Kim","year":"2005","journal-title":"Plant Cell"},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"649","DOI":"10.1128\/jb.93.2.649-655.1967","article-title":"Bacterial Oxidation of 2-Tridecanone to 1-Undecanol","volume":"93","author":"Forney","year":"1967","journal-title":"J. Bacteriol."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"31","DOI":"10.1016\/0006-291X(69)90876-6","article-title":"An enzyme system for aliphatic methyl ketone oxidation","volume":"37","author":"Forney","year":"1969","journal-title":"Biochem. Biophys. Res. Commun."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"363","DOI":"10.1042\/bj1210363","article-title":"The metabolism of cyclohexanol by Nocardia globerula CL1","volume":"121","author":"Norris","year":"1971","journal-title":"Biochem. J."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"175","DOI":"10.1111\/j.1432-1033.1976.tb10220.x","article-title":"The purification and properties of cyclohexanone oxygenase from Nocardia globerula CL1 and Acinetobacter NCIB 9871","volume":"63","author":"Donoghue","year":"1976","journal-title":"Eur. J. Biochem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"333","DOI":"10.1002\/anie.198803331","article-title":"Enzymic Baeyer-Villiger oxidations by flavin-dependent monooxygenases","volume":"27","author":"Walsh","year":"1988","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"41","DOI":"10.1016\/0045-2068(89)90006-0","article-title":"Enzymatic Baeyer-Villiger type oxidations of ketones catalyzed by cyclohexanone oxygenase","volume":"17","author":"Abril","year":"1989","journal-title":"Bioorg. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"8245","DOI":"10.1039\/C5NJ02093J","article-title":"Oxoiron(IV)-mediated Baeyer-Villiger oxidation of cyclohexanones generated by dioxygen with co-oxidation of aldehydes","volume":"39","author":"Speier","year":"2015","journal-title":"New J. Chem."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"141","DOI":"10.1016\/j.inoche.2018.04.024","article-title":"Kinetics and enantioselectivity of the Baeyer-Villiger oxidation of cyclohexanones by chiral tetrapyridyl oxoiron(IV) complex","volume":"92","author":"Turcas","year":"2018","journal-title":"Inorg. Chem. Commun."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"14290","DOI":"10.1002\/chem.201903727","article-title":"Stoichiometric Aldehyde Deformylation Mediated by nucleophilic Peroxo-diiron(III) Complex as a Functional Model of Aldehyde Deformylating Oxygenase","volume":"25","author":"Kripli","year":"2019","journal-title":"Chem. Eur. J."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"1742","DOI":"10.1039\/C9DT04551A","article-title":"Functional models of nonheme diiron enzymes: Reactivity of the m-oxo-m-1,2-peroxo-diiron(III) intermediate in electrophilic and nucleophilic reactions","volume":"49","author":"Kripli","year":"2020","journal-title":"Dalton Trans."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"7181","DOI":"10.1039\/D1DT01502H","article-title":"A nonheme peroxo-diiron(III) complex exhibiting both nucleophilic and electrophilic oxidation of organic substrates","volume":"50","author":"Unjaroen","year":"2021","journal-title":"Dalton Trans."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"37","DOI":"10.1021\/acs.inorgchem.1c03468","article-title":"Nonheme Diiron Oxygenase Mimic That Generates a Diferric-Peroxo Intermediate Capable of Catalytic Olefin Epoxidation and Alkane Hydroxylation Including Cyclohexane","volume":"61","author":"Oloo","year":"2022","journal-title":"Inorg. Chem."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"1326","DOI":"10.1039\/C3CC48196D","article-title":"Stabilisation of \u03bc-peroxido-bridged Fe(III) intermediates with non-symmetric bidentate N-donor ligands","volume":"50","author":"Pap","year":"2014","journal-title":"Chem. Commun."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"14709","DOI":"10.1039\/C6DT01598K","article-title":"Functional models on nonheme diiron enzymes: Kinetic and computational evidence for the formation of oxoiron(IV) species from peroxo-diiron(III) complexes, and their reactivity towards phenols and H2O2","volume":"45","author":"Surducan","year":"2016","journal-title":"Dalton Trans."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"81","DOI":"10.1016\/j.inoche.2012.02.022","article-title":"Low temperature reaction of [Fe(TPA)(CH3CN)2]2+ with excess 3-chloroperoxybenzoic acid in semi-frozen acetonitrile; EPR detection of an acylperoxo iron(III) adduct","volume":"20","author":"Zhang","year":"2012","journal-title":"Inorg. Chem. Commun."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/9\/2814\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T23:03:32Z","timestamp":1760137412000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/27\/9\/2814"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2022,4,28]]},"references-count":42,"journal-issue":{"issue":"9","published-online":{"date-parts":[[2022,5]]}},"alternative-id":["molecules27092814"],"URL":"https:\/\/doi.org\/10.3390\/molecules27092814","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2022,4,28]]}}}