{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,4,11]],"date-time":"2026-04-11T17:51:59Z","timestamp":1775929919127,"version":"3.50.1"},"reference-count":117,"publisher":"MDPI AG","issue":"3","license":[{"start":{"date-parts":[[2024,1,28]],"date-time":"2024-01-28T00:00:00Z","timestamp":1706400000000},"content-version":"vor","delay-in-days":0,"URL":"https:\/\/creativecommons.org\/licenses\/by\/4.0\/"}],"funder":[{"name":"Unione Europea\u2014NextGenerationEU","award":["D.M. 737\/2021"],"award-info":[{"award-number":["D.M. 737\/2021"]}]},{"name":"Unione Europea\u2014NextGenerationEU","award":["FAR 2022 PNR"],"award-info":[{"award-number":["FAR 2022 PNR"]}]},{"name":"Unione Europea\u2014NextGenerationEU","award":["351\/2022 M4C1 I4.1"],"award-info":[{"award-number":["351\/2022 M4C1 I4.1"]}]},{"name":"Unione Europea\u2014NextGenerationEU","award":["PRID BIRD225980"],"award-info":[{"award-number":["PRID BIRD225980"]}]},{"DOI":"10.13039\/501100003500","name":"University of Padova","doi-asserted-by":"publisher","award":["D.M. 737\/2021"],"award-info":[{"award-number":["D.M. 737\/2021"]}],"id":[{"id":"10.13039\/501100003500","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003500","name":"University of Padova","doi-asserted-by":"publisher","award":["FAR 2022 PNR"],"award-info":[{"award-number":["FAR 2022 PNR"]}],"id":[{"id":"10.13039\/501100003500","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003500","name":"University of Padova","doi-asserted-by":"publisher","award":["351\/2022 M4C1 I4.1"],"award-info":[{"award-number":["351\/2022 M4C1 I4.1"]}],"id":[{"id":"10.13039\/501100003500","id-type":"DOI","asserted-by":"publisher"}]},{"DOI":"10.13039\/501100003500","name":"University of Padova","doi-asserted-by":"publisher","award":["PRID BIRD225980"],"award-info":[{"award-number":["PRID BIRD225980"]}],"id":[{"id":"10.13039\/501100003500","id-type":"DOI","asserted-by":"publisher"}]}],"content-domain":{"domain":[],"crossmark-restriction":false},"short-container-title":["Molecules"],"abstract":"<jats:p>The new 3-monosubstituted acetylacetone ligands, 3-(phenyl(1H-pyrazol-1-yl)methyl)pentane-2,4-dione (HLacPz) and 3-((3,5-dimethyl-1H-pyrazol-1-yl)(phenyl)methyl)pentane-2,4-dione (HLacPzMe), were synthesized and used as supporting ligands for new copper(II) and copper(I) phosphane complexes of the general formulae [Cu(HLacX)2(LacX)2] and [Cu(PPh3)2(HLacX)]PF6 (X = Pz (pyrazole) or PzMe (3,5-dimethylpyrazole)), respectively. In the syntheses of the Cu(I) complexes, the triphenylphosphine coligand (PPh3) was used to stabilize copper in the +1 oxidation state, avoiding oxidation to Cu(II). All compounds were characterized by CHN analysis, 1H-NMR, 13C-NMR, FT-IR spectroscopy, and electrospray ionization mass spectrometry (ESI-MS). The ligands HLacPz (1) and HLacPzMe (2) and the copper complex [Cu(PPh3)2(HLacPz)]PF6 (3) were also characterized by X-ray crystallography. The reactivity of these new compounds was investigated and the new compounds 4-phenyl-4-(1H-pyrazol-1-yl)butan-2-one (7) and 4-(3,5-dimethyl-1H-pyrazol-1-yl)-4-phenylbutan-2-one (8) were obtained in basic conditions via the retro-Claisen reaction of related 3-monosubstituted acetylacetone, providing efficient access to synthetically useful ketone compounds. Compound 8 was also characterized by X-ray crystallography.<\/jats:p>","DOI":"10.3390\/molecules29030621","type":"journal-article","created":{"date-parts":[[2024,1,30]],"date-time":"2024-01-30T05:14:32Z","timestamp":1706591672000},"page":"621","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":7,"title":["New Copper Complexes with N,O-Donor Ligands Based on Pyrazole Moieties Supported by 3-Substituted Acetylacetone Scaffolds"],"prefix":"10.3390","volume":"29","author":[{"given":"Jo\u2019","family":"Del Gobbo","sequence":"first","affiliation":[{"name":"School of Science and Technology, Chemistry Division, University of Camerino, Via Madonna delle Carceri (ChIP), Camerino, 62032 Macerata, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-3942-1713","authenticated-orcid":false,"given":"Carlo","family":"Santini","sequence":"additional","affiliation":[{"name":"School of Science and Technology, Chemistry Division, University of Camerino, Via Madonna delle Carceri (ChIP), Camerino, 62032 Macerata, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0003-1287-6635","authenticated-orcid":false,"given":"Alessandro","family":"Dolmella","sequence":"additional","affiliation":[{"name":"Department of Pharmaceutical and Pharmacological Sciences, University of Padova, Via Marzolo 5, 35131 Padova, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Zhenzhen","family":"Li","sequence":"additional","affiliation":[{"name":"School of Science and Technology, Chemistry Division, University of Camerino, Via Madonna delle Carceri (ChIP), Camerino, 62032 Macerata, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"given":"Miriam","family":"Caviglia","sequence":"additional","affiliation":[{"name":"School of Science and Technology, Chemistry Division, University of Camerino, Via Madonna delle Carceri (ChIP), Camerino, 62032 Macerata, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-5020-1730","authenticated-orcid":false,"given":"Maura","family":"Pellei","sequence":"additional","affiliation":[{"name":"School of Science and Technology, Chemistry Division, University of Camerino, Via Madonna delle Carceri (ChIP), Camerino, 62032 Macerata, Italy"}],"role":[{"role":"author","vocabulary":"crossref"}]}],"member":"1968","published-online":{"date-parts":[[2024,1,28]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","first-page":"6617","DOI":"10.1021\/jo049274l","article-title":"Preparation of \u03b2-keto esters and \u03b2-diketones by C-acylation\/deacetylation of acetoacetic esters and acetonyl ketones with 1-acylbenzotriazoles","volume":"69","author":"Katritzky","year":"2004","journal-title":"J. Org. Chem."},{"key":"ref_2","doi-asserted-by":"crossref","first-page":"10359","DOI":"10.1016\/j.tet.2004.07.087","article-title":"New access to 1,3-diketones from aldehydes","volume":"60","author":"Fargeas","year":"2004","journal-title":"Tetrahedron"},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Sharma, Y., and Ansari, A. (2022). Diketones as building block in organic synthesis with versatile applications and medicinal properties. Mater. Today Proc., in press.","DOI":"10.1016\/j.matpr.2022.12.015"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"2765","DOI":"10.2174\/1385272825666210812102416","article-title":"Recent Developments in the Synthesis of Five- and Six-membered N-heterocycles from Dicarbonyl Compounds","volume":"25","author":"Kaur","year":"2021","journal-title":"Curr. Org. Chem."},{"key":"ref_5","unstructured":"Joule, J.A., and Mills, K. (2010). Heterocyclic Chemistry, Wiley. [5th ed.]."},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Hansen, P.A.-O. (2021). Structural Studies of \u03b2-Diketones and Their Implications on Biological Effects. Pharmaceuticals, 14.","DOI":"10.3390\/ph14111189"},{"key":"ref_7","doi-asserted-by":"crossref","first-page":"721","DOI":"10.1042\/BJ20042038","article-title":"Emergent mechanistic diversity of enzyme-catalysed \u03b2-diketone cleavage","volume":"388","author":"Grogan","year":"2005","journal-title":"Biochem. J."},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"73","DOI":"10.1016\/S1381-1177(02)00153-4","article-title":"\u03b2-diketone hydrolases","volume":"19","author":"Grogan","year":"2002","journal-title":"J. Mol. Catal. B Enzym."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"291","DOI":"10.1016\/S0167-7799(97)01055-X","article-title":"\u03b2-ketolases-Forgotten hydrolytic enzymes?","volume":"15","author":"Pokorny","year":"1997","journal-title":"Trends Biotechnol."},{"key":"ref_10","doi-asserted-by":"crossref","unstructured":"Hozakova, L., Vokata, B., Ruml, T., and Ulbrich, P. (2022). Targeting the Virus Capsid as a Tool to Fight RNA Viruses. Viruses, 14.","DOI":"10.3390\/v14020174"},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"12500","DOI":"10.1039\/D2NJ01480G","article-title":"Casiopeinas\u00ae as SARS-CoV-2 main protease (Mpro) inhibitors: A combined DFT, molecular docking and ONIOM approach","volume":"46","author":"Reina","year":"2022","journal-title":"New J. Chem."},{"key":"ref_12","doi-asserted-by":"crossref","first-page":"957","DOI":"10.1016\/S0010-8545(01)00389-7","article-title":"Metalloaromaticity","volume":"219\u2013221","author":"Masui","year":"2001","journal-title":"Coord. Chem. Rev."},{"key":"ref_13","unstructured":"Wilkinson, G., Gillard, R.D., and McCleverty, J.A. (1987). Comprehensive Coordination Chemistry, Pergamon."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"51","DOI":"10.1016\/0010-8545(86)80035-2","article-title":"Variety in the coordination modes of \u03b2-dicarbonyl compounds in metal complexes","volume":"70","author":"Kawaguchi","year":"1986","journal-title":"Coord. Chem. Rev."},{"key":"ref_15","unstructured":"Mehrotra, R.C., Bohra, R., and Gaur, D.P. (1978). Metal [Beta]-Diketonates and Allied Derivatives, Academic Press."},{"key":"ref_16","unstructured":"Constable, E.C., Parkin, G., and Que, L. (2021). Comprehensive Coordination Chemistry III, Elsevier."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"9847","DOI":"10.1021\/jacs.7b06288","article-title":"Enabling the Cross-Coupling of Tertiary Organoboron Nucleophiles through Radical-Mediated Alkyl Transfer","volume":"139","author":"Primer","year":"2017","journal-title":"J. Am. Chem. Soc."},{"key":"ref_18","doi-asserted-by":"crossref","first-page":"343","DOI":"10.1038\/nature14006","article-title":"Functionalized olefin cross-coupling to construct carbon-carbon bonds","volume":"516","author":"Lo","year":"2014","journal-title":"Nature"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"8742","DOI":"10.1021\/ja063063b","article-title":"Highly selective room-temperature copper-catalyzed C-N coupling reactions","volume":"128","author":"Shafir","year":"2006","journal-title":"J. Am. Chem. Soc."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"5112","DOI":"10.1021\/ja0040971","article-title":"Diastereoselective cobalt-catalyzed Aldol and Michael cycloreductions","volume":"123","author":"Baik","year":"2001","journal-title":"J. Am. Chem. Soc."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"1022","DOI":"10.1055\/s-2000-6673","article-title":"Copper-catalyzed N-arylation of amines with hypervalent iodonium salts","volume":"2000","author":"Kang","year":"2000","journal-title":"Synlett"},{"key":"ref_22","doi-asserted-by":"crossref","first-page":"569","DOI":"10.1246\/cl.1989.569","article-title":"Hydration of Olefins with Molecular Oxygen and Triethylsilane Catalyzed by Bis(trifluoroacetylacetonato)cobalt(II)","volume":"18","author":"Isayama","year":"1989","journal-title":"Chem. Lett."},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"12197","DOI":"10.1021\/acssuschemeng.8b02532","article-title":"Stabilizing Effect of Bulky \u03b2-Diketones on Homogeneous Mo Catalysts for Deoxydehydration","volume":"6","author":"Stalpaert","year":"2018","journal-title":"ACS Sustain. Chem. Eng."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"10714","DOI":"10.1039\/C9DT02293G","article-title":"Sterically encumbered \u03b2-diketonates and base metal catalysis","volume":"48","author":"Krajewski","year":"2019","journal-title":"Dalton Trans."},{"key":"ref_25","doi-asserted-by":"crossref","first-page":"7434","DOI":"10.1021\/acs.joc.9b00433","article-title":"Synthesis of Sterically Hindered \u03b2-Diketones via Condensation of Acid Chlorides with Enolates","volume":"84","author":"Crossman","year":"2019","journal-title":"J. Org. Chem."},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"11466","DOI":"10.1021\/acs.inorgchem.7b02077","article-title":"Bulky \u03b2-Diketones Enabling New Lewis Acidic Ligand Platforms","volume":"56","author":"Akturk","year":"2017","journal-title":"Inorg. Chem."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"1031","DOI":"10.1007\/s10947-005-0096-4","article-title":"Regularities of crystal structures of Cu(II) \u03b2-diketonates","volume":"45","author":"Gromilov","year":"2004","journal-title":"J. Struct. Chem."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"8200","DOI":"10.1021\/jp004531l","article-title":"Electronic Structure of 1,5-Cyclooctadiene-copper(I)-hexafluoroacetylacetonate","volume":"105","author":"Bulusheva","year":"2001","journal-title":"J. Phys. Chem. A"},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"2293","DOI":"10.1016\/S0277-5387(00)86153-7","article-title":"The chemistry of \u03b2-diketonate copper(I) compounds\u2014III. The synthesis of (\u03b2-diketonate) Cu(1,5-COD) compounds, the solid state structure and disproportionation of hexafluoroacetylacetonato (1,5-cyclooctadiene)copper(I), (hfac)Cu(1,5-COD)","volume":"10","author":"Chi","year":"1991","journal-title":"Polyhedron"},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"2127","DOI":"10.1002\/cber.19630960822","article-title":"Zur Kenntnis von Kupfer(I)-acetylacetonat","volume":"96","author":"Nast","year":"1963","journal-title":"Chem. Berichte"},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"423","DOI":"10.1021\/acs.inorgchem.9b02721","article-title":"Copper(II) as a Platform for Probing the Steric Demand of Bulky \u03b2-Diketonates","volume":"59","author":"Larson","year":"2020","journal-title":"Inorg. Chem."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"48","DOI":"10.1016\/j.ica.2013.11.019","article-title":"Chemical and electrochemical oxidation studies on new copper(I) ferrocenyl-functionalised \u03b2-diketonates","volume":"411","author":"Jakob","year":"2014","journal-title":"Inorg. Chim. Acta"},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"2371","DOI":"10.1002\/zaac.200300253","article-title":"Mono- and bimetallic copper(I)- and silver(I)-phosphane complexes with \u03b2-diketonate units","volume":"629","author":"Lang","year":"2003","journal-title":"Z. Anorg. Allg. Chem."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"585","DOI":"10.1016\/S0277-5387(01)00715-X","article-title":"Synthesis of copper(I) \u03b2-diketone complexes","volume":"20","author":"Yang","year":"2001","journal-title":"Polyhedron"},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"424","DOI":"10.1021\/ic00029a015","article-title":"Chemistry of copper(I).beta.-diketonate complexes. 2. Synthesis, characterization, and physical properties of (.beta.-diketonato)copper(I) trimethylphosphine and bis(trimethylphosphine) complexes","volume":"31","author":"Shin","year":"1992","journal-title":"Inorg. Chem."},{"key":"ref_36","doi-asserted-by":"crossref","unstructured":"Chi, K.-M., Farkas, J., Hampden-Smith, M.J., Kodas, T.T., and Duesler, E.N. (1992). The chemistry of copper(I)\u03b2-diketonate compounds. Part 4. Syntheses and characterization of CuXL(X = \u03b2-diketonate or Cl, L = PMe3, n = 2 or 4; L = PEt3, n = 2). Dalton Trans., 3111\u20133117.","DOI":"10.1039\/DT9920003111"},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"2954","DOI":"10.1139\/v92-377","article-title":"The chemistry of copper(I) \u03b2-diketonate compounds. Part V. Syntheses and characterization of (\u03b2-diketonate)CuLn species where L = PBu3, PPh3, and PCy3; n = 1 and 2; crystal and molecular structures of (acac)Cu(PCy3), (tfac)Cu(PCy3), (hfac)Cu(PCy3), and (hfac)Cu(PCy3)2","volume":"70","author":"Shin","year":"1992","journal-title":"Can. J. Chem."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"365","DOI":"10.1021\/cm00020a025","article-title":"A novel copper complex and CVD precursor: (.eta.2-butyne)copper(I) hexafluoroacetylacetonate","volume":"4","author":"Baum","year":"1992","journal-title":"Chem. Mater."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"2332","DOI":"10.1063\/1.106060","article-title":"Chemical vapor deposition of copper from 1,5-cyclooctadiene copper(I) exafluoroacetylacetonate","volume":"59","author":"Reynolds","year":"1991","journal-title":"J. Appl. Phys. Lett."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"216","DOI":"10.1021\/cm00009a002","article-title":"Low-temperature chemical vapor deposition of high purity copper from an organometallic source","volume":"2","author":"Beach","year":"1990","journal-title":"Chem. Mater."},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"795","DOI":"10.1139\/v83-146","article-title":"Triplet-state benzophenone-sensitized photoreduction of bis(acetylacetonato)copper(II): The generation and stability of copper(I) complexes","volume":"61","author":"Chow","year":"1983","journal-title":"Can. J. Chem."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"1949","DOI":"10.1139\/v75-272","article-title":"Perchlorato, Nitrato, and Acetylacetonato Complexes of Copper(I). The Crystal and Molecular Structure of Perchloratobis(tricyclohexyiphosphine)Copper(I)","volume":"53","author":"Restivo","year":"1975","journal-title":"Can. J. Chem."},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"761","DOI":"10.1139\/v71-127","article-title":"Nitrato and Acetylacetonato Complexes of Copper(I)","volume":"49","author":"Anderson","year":"1971","journal-title":"Can. J. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","unstructured":"Khamidullina, L.A., Puzyrev, I.S., Burygin, G.L., Dorovatovskii, P.V., Zubavichus, Y.V., Mitrofanova, A.V., Khrustalev, V.N., Timofeeva, T.V., Slepukhin, P.A., and Tobysheva, P.D. (2021). Unsymmetrical Trifluoromethyl Methoxyphenyl \u03b2-Diketones: Effect of the Position of Methoxy Group and Coordination at Cu(II) on Biological Activity. Molecules, 26.","DOI":"10.3390\/molecules26216466"},{"key":"ref_45","doi-asserted-by":"crossref","unstructured":"Pellei, M., Santini, C., Bagnarelli, L., Caviglia, M., Sgarbossa, P., De Franco, M., Zancato, M., Marzano, C., and Gandin, V. (2023). Novel Silver Complexes Based on Phosphanes and Ester Derivatives of Bis(pyrazol-1-yl)acetate Ligands Targeting TrxR: New Promising Chemotherapeutic Tools Relevant to SCLC Management. Int. J. Mol. Sci., 24.","DOI":"10.3390\/ijms24044091"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"4919","DOI":"10.1021\/acs.inorgchem.1c03658","article-title":"Cu(I) and Cu(II) Complexes Based on Lonidamine-Conjugated Ligands Designed to Promote Synergistic Antitumor Effects","volume":"61","author":"Pellei","year":"2022","journal-title":"Inorg. Chem."},{"key":"ref_47","doi-asserted-by":"crossref","unstructured":"Pellei, M., Bagnarelli, L., Luciani, L., Del Bello, F., Giorgioni, G., Piergentili, A., Quaglia, W., De Franco, M., Gandin, V., and Marzano, C. (2020). Synthesis and Cytotoxic Activity Evaluation of New Cu(I) Complexes of Bis(pyrazol-1-yl) Acetate Ligands Functionalized with an NMDA Receptor Antagonist. Int. J. Mol. Sci., 21.","DOI":"10.3390\/ijms21072616"},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"11878","DOI":"10.1039\/C8NJ01763H","article-title":"Novel antitumor copper(ii) complexes designed to act through synergistic mechanisms of action, due to the presence of an NMDA receptor ligand and copper in the same chemical entity","volume":"42","author":"Morelli","year":"2018","journal-title":"New J. Chem."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"13936","DOI":"10.1038\/s41598-017-13698-1","article-title":"Therapeutic potential of the phosphino Cu(I) complex (HydroCuP) in the treatment of solid tumors","volume":"7","author":"Gandin","year":"2017","journal-title":"Sci. Rep."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"80","DOI":"10.1016\/j.jinorgbio.2016.07.007","article-title":"Insights into the cytotoxic activity of the phosphane copper(I) complex Cu(thp)4PF6","volume":"165","author":"Tisato","year":"2016","journal-title":"J. Inorg. Biochem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"1103","DOI":"10.1016\/j.inoche.2008.06.005","article-title":"New homoleptic carbene transfer ligands and related coinage metal complexes","volume":"11","author":"Papini","year":"2008","journal-title":"Inorg. Chem. Commun."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"12098","DOI":"10.1039\/D3DT02179C","article-title":"Synthesis and cytotoxicity studies of Cu(I) and Ag(I) complexes based on sterically hindered \u03b2-diketonates with different degrees of fluorination","volume":"52","author":"Pellei","year":"2023","journal-title":"Dalton Trans."},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"147","DOI":"10.1007\/BFb0111456","article-title":"The composition, structure and hydrogen bonding of the \u03b2-diketones","volume":"Volume 57","author":"Emsley","year":"1984","journal-title":"Complex Chemistry"},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1706","DOI":"10.1021\/acs.orglett.3c00372","article-title":"Asymmetric Retro-Claisen Reaction Catalyzed by Chiral Aza-Bisoxazoline\u2013Zn(II) Complex: Enantioselective Synthesis of \u03b1-Arylated Ketones","volume":"25","author":"Liu","year":"2023","journal-title":"Org. Lett."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"773","DOI":"10.1070\/RC1971v040n09ABEH001969","article-title":"Investigation of Keto\u2013Enol Tautomerism by Nuclear Magnetic Resonance Spectroscopy","volume":"40","author":"Kheifets","year":"1971","journal-title":"Russ. Chem. Rev."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"3190","DOI":"10.1246\/bcsj.42.3190","article-title":"Tautomerism in 3-Substituted-2,4-pentanediones and Their Copper Chelates","volume":"42","author":"Tanaka","year":"1969","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"30","DOI":"10.1021\/acs.cgd.8b01406","article-title":"Controlled Synthesis of Supramolecular Architectures of Homo- and Heterometallic Complexes by Programmable Self-Assembly","volume":"19","author":"Tong","year":"2019","journal-title":"Cryst. Growth Des."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"121","DOI":"10.1016\/j.ccr.2017.08.005","article-title":"Assembling latter d-block heterometal coordination polymers: Synthetic strategies and structural outcomes","volume":"348","author":"Lee","year":"2017","journal-title":"Coord. Chem. Rev."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"7001","DOI":"10.1021\/cr5005666","article-title":"Recent Developments in the Preparation and Chemistry of Metallacycles and Metallacages via Coordination","volume":"115","author":"Cook","year":"2015","journal-title":"Chem. Rev."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"139","DOI":"10.1016\/j.ccr.2014.08.014","article-title":"Multi-component coordination-driven self-assembly toward heterometallic macrocycles and cages","volume":"293\u2013294","author":"Li","year":"2015","journal-title":"Coord. Chem. Rev."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"1619","DOI":"10.1039\/C2CS35123D","article-title":"Functional behaviour from controlled self-assembly: Challenges and prospects","volume":"42","author":"Ward","year":"2013","journal-title":"Chem. Soc. Rev."},{"key":"ref_62","doi-asserted-by":"crossref","first-page":"3113","DOI":"10.1016\/S0277-5387(01)00935-4","article-title":"An effective synthesis of alkyl \u03b2-cyano-\u03b1,\u03b3-diketones using chlorosulfonylisocyanate and a representative Cu(II) complex","volume":"20","author":"Silvernail","year":"2001","journal-title":"Polyhedron"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"118","DOI":"10.1016\/S0020-1693(00)00058-X","article-title":"Reactions of dicarbonyltitanocenes with 2-diazo-1,3-diketones: O-,N-versus O-,O-chelation and self-assembly of a novel heteroleptic Ti5O6-cage compound","volume":"304","author":"Nieuwenhuyzen","year":"2000","journal-title":"Inorg. Chim. Acta"},{"key":"ref_64","doi-asserted-by":"crossref","unstructured":"Turner, S.S., Collison, D., Mabbs, F.E., and Halliwell, M. (1997). Preparation, magnetic properties and crystal structure of bis 3-(4-pyridyl)pentane-2,4-dionato copper(II). J. Chem. Soc. Dalton Trans., 1117\u20131118.","DOI":"10.1039\/a700198c"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"1097","DOI":"10.1016\/S0277-5387(00)00358-2","article-title":"gamma-Halogenated iridium(III) acetylacetonates","volume":"19","author":"Isakova","year":"2000","journal-title":"Polyhedron"},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"3178","DOI":"10.1021\/acs.inorgchem.2c04101","article-title":"A Rigid Linker for Site-Selective Coordination of Transition Metal Cations: Combining an Acetylacetone with a Caged Phosphine","volume":"62","author":"Gildenast","year":"2023","journal-title":"Inorg. Chem."},{"key":"ref_67","doi-asserted-by":"crossref","first-page":"1041","DOI":"10.1039\/C9CE01932D","article-title":"3-(4-Methylthiophenyl)acetylacetone\u2013ups and downs of flexibility in the synthesis of mixed metal\u2013organic frameworks. Ditopic bridging of hard and soft cations and site-specific desolvation","volume":"22","author":"Gildenast","year":"2020","journal-title":"CrystEngComm"},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"5127","DOI":"10.1021\/acs.cgd.6b00710","article-title":"An Acetylacetonate or a Pyrazole? Both! 3-(3,5-Dimethyl-pyrazol-4-yl)pentane-2,4-dione as a Ditopic Ligand","volume":"16","author":"Guo","year":"2016","journal-title":"Cryst. Growth Des."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"2962","DOI":"10.1021\/acs.cgd.1c00122","article-title":"N-Donor-Functionalized Acetylacetones for Heterobimetallic Coordination Polymers, the Next Episode: Trimethylpyrazoles","volume":"21","author":"Nachtigall","year":"2021","journal-title":"Cryst. Growth Des."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"4383","DOI":"10.1039\/C5CE00043B","article-title":"Crosslinking of the Pd(acacCN)2 building unit with Ag(I) salts: Dynamic 1D polymers and an extended 3D network","volume":"17","author":"Guo","year":"2015","journal-title":"Crystengcomm"},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"705","DOI":"10.1107\/S2052520614006210","article-title":"3-(4-Pyridyl)-acetylacetone-a fully featured substituted pyridine and a flexible linker for complex materials","volume":"70","author":"Merkens","year":"2014","journal-title":"Acta Crystallogr. Sect. B Struct. Sci. Cryst. Eng. Mater."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"340","DOI":"10.1002\/zaac.201200386","article-title":"Crystal-to-Crystal Transformations in a Seven-Coordinated Scandium Complex","volume":"639","author":"Merkens","year":"2013","journal-title":"Z. Anorg. Allg. Chem."},{"key":"ref_73","doi-asserted-by":"crossref","first-page":"8153","DOI":"10.1039\/c3ce41306c","article-title":"3-(4-Pyridyl)-2,4-pentanedione-a bridge between coordinative, halogen, and hydrogen bonds","volume":"15","author":"Merkens","year":"2013","journal-title":"Crystengcomm"},{"key":"ref_74","doi-asserted-by":"crossref","first-page":"4664","DOI":"10.1039\/c2dt11772j","article-title":"Ordered bimetallic coordination networks featuring rare earth and silver cations","volume":"41","author":"Merkens","year":"2012","journal-title":"Dalton Trans."},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"8594","DOI":"10.1039\/c2dt30623a","article-title":"Bimetallic coordination networks based on Al(acacCN)3: A building block between inertness and lability","volume":"41","author":"Merkens","year":"2012","journal-title":"Dalton Trans."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"10246","DOI":"10.1021\/ic800748f","article-title":"Bimetallic Coordination Polymers via Combination of Substitution-inert Building Blocks and Labile Connectors","volume":"47","author":"Kondracka","year":"2008","journal-title":"Inorg. Chem."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"4433","DOI":"10.1021\/ic800183v","article-title":"A nanoporous Ag-Fe mixed-metal-organic framework exhibiting single-crystal-to-single-crystal transformations upon guest exchange","volume":"47","author":"Zhang","year":"2008","journal-title":"Inorg. Chem."},{"key":"ref_78","doi-asserted-by":"crossref","unstructured":"Burrows, A.D., Cassar, K., Mahon, M.F., and Warren, J.E. (2007). The stepwise formation of mixed-metal coordination networks using complexes of 3-cyanoacetylacetonate. Dalton Trans., 2499\u20132509.","DOI":"10.1039\/b702074k"},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"917","DOI":"10.1016\/j.poly.2005.02.023","article-title":"Heterobimetallic Cd(Zn)\/Be coordination polymers involving pyridyl functionalized beryllium diketonates","volume":"24","author":"Vreshch","year":"2005","journal-title":"Polyhedron"},{"key":"ref_80","doi-asserted-by":"crossref","first-page":"8209","DOI":"10.1021\/ic048992n","article-title":"Porous Cu-Cd mixed-metal-organic frameworks constructed from Cu(PyaC)2 {Bis 3-(4-pyridyl)pentane-2,4-dionato copper(II)}","volume":"43","author":"Chen","year":"2004","journal-title":"Inorg. Chem."},{"key":"ref_81","doi-asserted-by":"crossref","unstructured":"Vreshch, V.D., Lysenko, A.B., Chernega, A.N., Howard, J.A.K., Krautscheid, H., Sieler, J., and Domasevitch, K.V. (2004). Extended coordination frameworks incorporating heterobimetallic squares. Dalton Trans., 2899\u20132903.","DOI":"10.1039\/b407244h"},{"key":"ref_82","doi-asserted-by":"crossref","unstructured":"Vreshch, V.D., Chernega, A.N., Howard, J.A.K., Sieler, J., and Domasevitch, K.V. (2003). Two-step construction of molecular and polymeric mixed-metal Cu(Co)\/Be complexes employing functionality of a pyridyl substituted acetylacetonate. Dalton Trans., 1707\u20131711.","DOI":"10.1039\/b212733d"},{"key":"ref_83","doi-asserted-by":"crossref","first-page":"3435","DOI":"10.1002\/1521-3773(20010917)40:18<3435::AID-ANIE3435>3.0.CO;2-M","article-title":"Acentric extended solids by self assembly of 4,4\u2032-bipyrazolyls","volume":"40","author":"Boldog","year":"2001","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_84","doi-asserted-by":"crossref","unstructured":"Mackay, L.G., Anderson, H.L., and Sanders, J.K.M. (1992). A platinum-linked cyclic porphyrin trimer. J. Chem. Soc. Chem. Commun., 43\u201344.","DOI":"10.1039\/c39920000043"},{"key":"ref_85","doi-asserted-by":"crossref","first-page":"437","DOI":"10.1515\/zkri-2017-2131","article-title":"N Donor substituted acetylacetones\u2013versatile ditopic ligands","volume":"233","author":"Kremer","year":"2018","journal-title":"Z. F\u00fcr Krist. Cryst. Mater."},{"key":"ref_86","doi-asserted-by":"crossref","first-page":"9877","DOI":"10.1039\/c1dt10486a","article-title":"Nitroimidazole and glucosamine conjugated heteroscorpionate ligands and related copper(II) complexes. Syntheses, biological activity and XAS studies","volume":"40","author":"Pellei","year":"2011","journal-title":"Dalton Trans."},{"key":"ref_87","doi-asserted-by":"crossref","unstructured":"Pearson, R.G. (1997). Chemical Hardness, Wiley-VCH Verlag GmbH.","DOI":"10.1002\/3527606173"},{"key":"ref_88","doi-asserted-by":"crossref","first-page":"137","DOI":"10.1002\/anie.198001371","article-title":"\u03b2-Azolyl-\u03b1,\u03b1-dicarbonyl compounds","volume":"19","author":"Maier","year":"1980","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_89","doi-asserted-by":"crossref","first-page":"867","DOI":"10.1016\/j.saa.2013.09.109","article-title":"Lasing the DNA fragments through \u03b2-diketimine framed Knoevenagel condensed Cu(II) and Zn(II) complexes\u2013An in vitro and in vivo approach","volume":"118","author":"Raman","year":"2014","journal-title":"Spectrochim. Acta Part A"},{"key":"ref_90","doi-asserted-by":"crossref","first-page":"835","DOI":"10.1246\/bcsj.51.835","article-title":"The Reductive Deacylation of the Knoevenagel Condensates by the Use of the Tetracarbonylhydridoferrate(0) Anion. A New Synthetic Route of Ketones from Aldehydes","volume":"51","author":"Yamashita","year":"1978","journal-title":"Bull. Chem. Soc. Jpn."},{"key":"ref_91","doi-asserted-by":"crossref","first-page":"206","DOI":"10.1021\/om501053k","article-title":"Revealing the Ligand Effect on Copper(I) Disproportionation via Operando IR Spectra","volume":"34","author":"Cheng","year":"2014","journal-title":"Organometallics"},{"key":"ref_92","doi-asserted-by":"crossref","first-page":"12970","DOI":"10.1039\/C8CC07329E","article-title":"An efficient method for retro-Claisen-type C-C bond cleavage of diketones with tropylium catalyst","volume":"54","author":"Hussein","year":"2018","journal-title":"Chem. Commun."},{"key":"ref_93","first-page":"965","article-title":"Synthesis and biological evaluation of some novel quinoline based pyrimidine derivatives","volume":"57","author":"Desai","year":"2018","journal-title":"Indian J. Chem. Sect. B Org. Chem. Incl. Med. Chem."},{"key":"ref_94","doi-asserted-by":"crossref","first-page":"744","DOI":"10.1016\/j.tetlet.2017.01.026","article-title":"Unexpected formation of diethyl 2-ethoxy-6-CF3-2H-pyran-3,5-dicarboxylate from the condensation of ethyl 4,4,4-trifluoroacetoacetate with CH(OEt)3","volume":"58","author":"Kudyakova","year":"2017","journal-title":"Tetrahedron Lett."},{"key":"ref_95","doi-asserted-by":"crossref","first-page":"28","DOI":"10.1016\/j.jfluchem.2016.04.009","article-title":"Detrifluoroacetylation of 4,4,4-trifluoro-3,3-dihydroxy-2-(hydroxyimino)butan-1-ones as a convenient synthetic strategy for acyl cyanides","volume":"186","author":"Bazhin","year":"2016","journal-title":"J. Fluor. Chem."},{"key":"ref_96","doi-asserted-by":"crossref","first-page":"4171","DOI":"10.1021\/jo400280p","article-title":"Synthesis of Trifluoromethyl Ketones via Tandem Claisen Condensation and Retro-Claisen C-C Bond-Cleavage Reaction","volume":"78","author":"Yang","year":"2013","journal-title":"J. Org. Chem."},{"key":"ref_97","doi-asserted-by":"crossref","first-page":"2861","DOI":"10.1002\/ejoc.201000128","article-title":"An Efficient Iron-Catalyzed Carbon-Carbon Single-Bond Cleavage via Retro-Claisen Condensation: A Mild and Convenient Approach to Synthesize a Variety of Esters or Ketones","volume":"2010","author":"Biswas","year":"2010","journal-title":"Eur. J. Org. Chem."},{"key":"ref_98","doi-asserted-by":"crossref","first-page":"1677","DOI":"10.1002\/adsc.201300232","article-title":"C-C Hydrolases for Biocatalysis","volume":"355","author":"Siirola","year":"2013","journal-title":"Adv. Synth. Catal."},{"key":"ref_99","doi-asserted-by":"crossref","first-page":"29502","DOI":"10.1039\/C4RA04618H","article-title":"Base-catalyzed retro-Claisen condensation: A convenient esterification of alcohols via C-C bond cleavage of ketones to afford acylating sources","volume":"4","author":"Xie","year":"2014","journal-title":"Rsc Adv."},{"key":"ref_100","doi-asserted-by":"crossref","first-page":"488","DOI":"10.2174\/157017912802651438","article-title":"Recent Advances in the Retro-Claisen Reaction and Its Synthetic Applications","volume":"9","author":"Jukic","year":"2012","journal-title":"Curr. Org. Synth."},{"key":"ref_101","doi-asserted-by":"crossref","first-page":"2855","DOI":"10.1002\/ejoc.201000140","article-title":"Retro-Claisen Condensation with Fe-III as Catalyst under Solvent-Free Conditions","volume":"2010","author":"Rao","year":"2010","journal-title":"Eur. J. Org. Chem."},{"key":"ref_102","doi-asserted-by":"crossref","first-page":"7793","DOI":"10.1002\/anie.200702798","article-title":"Indium-catalyzed retro-claisen condensation","volume":"46","author":"Kawata","year":"2007","journal-title":"Angew. Chem. Int. Ed. Engl."},{"key":"ref_103","unstructured":"Johnson, C.K. (1976). ORTEP, Report ORNL\u20135138."},{"key":"ref_104","unstructured":"New and Improved CSD\u2013The 2023 November Data Update (2023, December 27). Cambridge Structural Database (CSD). Available online: https:\/\/www.ccdc.cam.ac.uk\/discover\/blog\/new-and-improved-csd-the-2023-november-data-update\/."},{"key":"ref_105","doi-asserted-by":"crossref","first-page":"380","DOI":"10.1107\/S0108768102003890","article-title":"The Cambridge Structural Database: A quarter of a million crystal structures and rising","volume":"58","author":"Allen","year":"2002","journal-title":"Acta Crystallogr. Sect. B Struct. Sci."},{"key":"ref_106","first-page":"o1529","article-title":"Ethyl N-(2-acetyl-3-oxo-1-phenylbutyl)carbamate","volume":"69","author":"Volov","year":"2013","journal-title":"Acta Crystallogr. Sect. E Crystallogr. Commun."},{"key":"ref_107","doi-asserted-by":"crossref","unstructured":"Gotsko, M.D., Saliy, I.V., Vashchenko, A.V., and Trofimov, B.A. (2022). 1-Phenyl-3,3-di(1H-pyrazol-1-yl)propan-1-one. Molbank, 2022.","DOI":"10.3390\/M1472"},{"key":"ref_108","doi-asserted-by":"crossref","first-page":"2319","DOI":"10.1016\/j.jorganchem.2009.03.037","article-title":"3,3-Bis(3,5-dimethylpyrazol-1-yl)propionic acid: A tripodal N,N,O ligand for manganese and rhenium complexes-Syntheses and structures","volume":"694","author":"Peters","year":"2009","journal-title":"J. Organomet. Chem."},{"key":"ref_109","doi-asserted-by":"crossref","first-page":"471","DOI":"10.1002\/zaac.200801298","article-title":"Functionalised Tris(pyrazolyl)methane Ligands and Re(CO)3 Complexes Thereof","volume":"635","author":"Kunz","year":"2009","journal-title":"Z. Anorg. Allg. Chem."},{"key":"ref_110","doi-asserted-by":"crossref","first-page":"466","DOI":"10.1107\/S0021889807067908","article-title":"Mercury CSD 2.0-New features for the visualization and investigation of crystal structures","volume":"41","author":"Macrae","year":"2008","journal-title":"J. Appl. Crystallogr."},{"key":"ref_111","unstructured":"Malecki, J.G. Personal communication."},{"key":"ref_112","doi-asserted-by":"crossref","first-page":"47","DOI":"10.1016\/j.poly.2015.01.035","article-title":"Coordination polymers and molecular structures among complexes of mercury(II) halides with selected 1-benzoylthioureas","volume":"90","author":"Okuniewski","year":"2015","journal-title":"Polyhedron"},{"key":"ref_113","doi-asserted-by":"crossref","unstructured":"Yang, L., Powell, D.R., and Houser, R.P. (2007). Structural variation in copper(I) complexes with pyridylmethylamide ligands: Structural analysis with a new four-coordinate geometry index, \u03c44. Dalton Trans., 955\u2013964.","DOI":"10.1039\/B617136B"},{"key":"ref_114","unstructured":"(2022). CrysAlisPro. Versions 1.171.41.123a and 1.171.42.49 (Rigaku Oxford Diffraction)."},{"key":"ref_115","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053273314026370","article-title":"SHELXT-Integrated space-group and crystal-structure determination","volume":"A71","author":"Sheldrick","year":"2015","journal-title":"Acta Crystallogr. Sect. A Found. Adv."},{"key":"ref_116","doi-asserted-by":"crossref","first-page":"3","DOI":"10.1107\/S2053229614024218","article-title":"Crystal structure refinement with SHELXL","volume":"C71","author":"Sheldrick","year":"2015","journal-title":"Acta Crystallogr. Sect. C Struct. Chem."},{"key":"ref_117","doi-asserted-by":"crossref","first-page":"339","DOI":"10.1107\/S0021889808042726","article-title":"OLEX2: A complete structure solution, refinement and analysis program","volume":"42","author":"Dolomanov","year":"2009","journal-title":"J. Appl. Crystallogr."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/3\/621\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,10]],"date-time":"2025-10-10T13:50:36Z","timestamp":1760104236000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/29\/3\/621"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2024,1,28]]},"references-count":117,"journal-issue":{"issue":"3","published-online":{"date-parts":[[2024,2]]}},"alternative-id":["molecules29030621"],"URL":"https:\/\/doi.org\/10.3390\/molecules29030621","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2024,1,28]]}}}