{"status":"ok","message-type":"work","message-version":"1.0.0","message":{"indexed":{"date-parts":[[2026,10,10]],"date-time":"2026-10-10T04:21:51Z","timestamp":1791606111725,"version":"4.3.4"},"reference-count":79,"publisher":"MDPI AG","issue":"4","license":[{"start":{"date-parts":[[2025,2,17]],"date-time":"2025-02-17T00:00:00Z","timestamp":1739750400000},"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>The carbonylation at the benzyl C-Hal bonds (Hal = F, Cl) of a number of polyfluorinated alkylbenzenes and benzocycloalkenes using carbon monoxide in the presence of SbF5 is described. The reaction provided the corresponding \u03b1-arylcarboxylic acids or their methyl esters following aqueous or methanol treatment. The products of double carbonylation were obtained from bis(chloromethyl)tetrafluorobenzenes and benzal fluorides. For benzal chloride derivatives, the possibility of selective mono- or dicarbonylation was shown to depend on the amount of antimony pentafluoride. In the case of polyfluorinated secondary benzyl halides with a hydrogen atom at the \u03b1-carbon atom and vicinal fluorine atoms, the addition of CO was found to be accompanied by the elimination of HF, resulting in \u03b1,\u03b2-unsaturated \u03b1-arylcarboxylic acids. The double elimination of HF during the carbonylation of 1,4-dichloro-2,2,3,3,5,6,7,8-octafluorotetralin yielded dimethyl perfluoronaphthalene-1,4-dicarboxylate.<\/jats:p>","DOI":"10.3390\/molecules30040931","type":"journal-article","created":{"date-parts":[[2025,2,17]],"date-time":"2025-02-17T12:36:57Z","timestamp":1739795817000},"page":"931","update-policy":"https:\/\/doi.org\/10.3390\/mdpi_crossmark_policy","source":"Crossref","is-referenced-by-count":2,"title":["Carbonylation of Polyfluorinated Alkylbenzenes and Benzocycloalkenes at the Benzyl C-F and C-Cl Bonds Under the Action of CO\/SbF5"],"prefix":"10.3390","volume":"30","author":[{"ORCID":"https:\/\/orcid.org\/0000-0003-0267-4976","authenticated-orcid":false,"given":"Yaroslav V.","family":"Zonov","sequence":"first","affiliation":[{"name":"N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk 630090, Russia"},{"name":"Department of Natural Sciences, Novosibirsk State University, Pirogov Str. 1, Novosibirsk 630090, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Siqi","family":"Wang","sequence":"additional","affiliation":[{"name":"Daqing Petrochemical Research Center, PetroChina Company Limited, Daqing 163714, China"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-6079-3039","authenticated-orcid":false,"given":"Vladislav V.","family":"Komarov","sequence":"additional","affiliation":[{"name":"N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk 630090, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"given":"Victor M.","family":"Karpov","sequence":"additional","affiliation":[{"name":"N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk 630090, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0002-6621-6520","authenticated-orcid":false,"given":"Dmitriy A.","family":"Parkhomenko","sequence":"additional","affiliation":[{"name":"N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk 630090, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]},{"ORCID":"https:\/\/orcid.org\/0000-0001-9936-0900","authenticated-orcid":false,"given":"Tatyana V.","family":"Mezhenkova","sequence":"additional","affiliation":[{"name":"N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry SB RAS, Lavrentiev Ave. 9, Novosibirsk 630090, Russia"}],"role":[{"vocabulary":"crossref","role":"author"}]}],"member":"1968","published-online":{"date-parts":[[2025,2,17]]},"reference":[{"key":"ref_1","doi-asserted-by":"crossref","unstructured":"Chambers, R.D. (2004). Fluorine in Organic Chemistry, Blackwell Pub.","DOI":"10.1002\/9781444305371"},{"key":"ref_2","doi-asserted-by":"crossref","unstructured":"Kirsch, P. (2004). Modern Fluoroorganic Chemistry: Synthesis, Reactivity, Applications, Wiley. [1st ed.].","DOI":"10.1002\/352760393X"},{"key":"ref_3","doi-asserted-by":"crossref","unstructured":"Banks, R.E., Smart, B.E., and Tatlow, J.C. (1994). Organofluorine Chemistry: Principles and Commercial Applications, Springer.","DOI":"10.1007\/978-1-4899-1202-2"},{"key":"ref_4","doi-asserted-by":"crossref","first-page":"446","DOI":"10.1021\/cm102182x","article-title":"Halogenated Materials as Organic Semiconductors","volume":"23","author":"Tang","year":"2011","journal-title":"Chem. Mater."},{"key":"ref_5","doi-asserted-by":"crossref","first-page":"1003","DOI":"10.1039\/B611336B","article-title":"Fluorinated Organic Materials for Electronic and Optoelectronic Applications: The Role of the Fluorine Atom","volume":"10","author":"Babudri","year":"2007","journal-title":"Chem. Commun."},{"key":"ref_6","doi-asserted-by":"crossref","unstructured":"Ojima, I. (2009). Fluorine in Medicinal Chemistry and Chemical Biology, Wiley-Blackwell.","DOI":"10.1002\/9781444312096"},{"key":"ref_7","doi-asserted-by":"crossref","unstructured":"B\u00e9gu\u00e9, J.-P., and Bonnet-Delpon, D. (2008). Bioorganic and Medicinal Chemistry of Fluorine, John Wiley & Sons.","DOI":"10.1002\/9780470281895"},{"key":"ref_8","doi-asserted-by":"crossref","first-page":"320","DOI":"10.1039\/B610213C","article-title":"Fluorine in Medicinal Chemistry","volume":"37","author":"Purser","year":"2008","journal-title":"Chem. Soc. Rev."},{"key":"ref_9","doi-asserted-by":"crossref","first-page":"827","DOI":"10.1021\/cr040075b","article-title":"\u03b1-Fluorinated Ethers, Thioethers, and Amines: Anomerically Biased Species","volume":"105","author":"Leroux","year":"2005","journal-title":"Chem. Rev."},{"key":"ref_10","doi-asserted-by":"crossref","first-page":"1201","DOI":"10.4155\/fmc.14.53","article-title":"Medicinal Applications of Perfluoroalkylated Chain-Containing Compounds","volume":"6","author":"Kotora","year":"2014","journal-title":"Future Med. Chem."},{"key":"ref_11","doi-asserted-by":"crossref","first-page":"199","DOI":"10.1070\/RC1973v042n03ABEH002575","article-title":"Carbonylation of Polyunsaturated Hydrocarbons and of Saturated and Unsaturated Alcohols and Halogeno-Derivatives","volume":"42","author":"Eidus","year":"1973","journal-title":"Russ. Chem. Rev."},{"key":"ref_12","doi-asserted-by":"crossref","unstructured":"Falbe, J. (1980). New Syntheses with Carbon Monoxide, Springer.","DOI":"10.1007\/978-3-642-67452-5"},{"key":"ref_13","doi-asserted-by":"crossref","first-page":"864","DOI":"10.1021\/ja00211a027","article-title":"Electrophilic Reactions at Single Bonds. 22. Superacid-Catalyzed Electrophilic Formylation of Adamantane with Carbon Monoxide Competing with Koch-Haaf Carboxylation","volume":"110","author":"Farooq","year":"1988","journal-title":"J. Am. Chem. Soc."},{"key":"ref_14","doi-asserted-by":"crossref","first-page":"71","DOI":"10.1016\/j.jfluchem.2014.03.008","article-title":"The First Carbonylation of Perfluoroorganic Compounds: The Reactions of Perfluorobenzocyclobutene and Its Perfluoroalkyl and Pentafluorophenyl Derivatives with CO in SbF5 Medium","volume":"162","author":"Zonov","year":"2014","journal-title":"J. Fluor. Chem."},{"key":"ref_15","doi-asserted-by":"crossref","first-page":"117","DOI":"10.1016\/j.jfluchem.2016.06.014","article-title":"Transformations of Perfluorinated 1,2-Dialkyl-, 1,1- and 1,2-Alkylphenylbenzocyclobutenes to Indan-2-one and Isochromene Derivatives under the Action of CO\/SbF5","volume":"188","author":"Zonov","year":"2016","journal-title":"J. Fluor. Chem."},{"key":"ref_16","doi-asserted-by":"crossref","first-page":"24","DOI":"10.1016\/j.jfluchem.2018.07.014","article-title":"Carbonylation of Polyfluorinated Indans, Tetralins and Perfluoro-2,3- Dihydrobenzofuran under the Action of CO\/SbF5","volume":"214","author":"Zonov","year":"2018","journal-title":"J. Fluor. Chem."},{"key":"ref_17","doi-asserted-by":"crossref","first-page":"1103","DOI":"10.1134\/S1070428019080086","article-title":"Carbonylation of Polyfluorobenzocyclobutenones in a SbF5 Medium","volume":"55","author":"Zonov","year":"2019","journal-title":"Russ. J. Org. Chem."},{"key":"ref_18","doi-asserted-by":"crossref","unstructured":"Wang, S., Zonov, Y.V., Karpov, V.M., Luzina, O.A., and Mezhenkova, T.V. (2022). Carbonylation of Polyfluorinated 1-Arylalkan-1-ols and Diols in Superacids. Molecules, 27.","DOI":"10.3390\/molecules27248757"},{"key":"ref_19","doi-asserted-by":"crossref","first-page":"5481","DOI":"10.1021\/ja00852a028","article-title":"Stable Carbocations","volume":"97","author":"Olah","year":"1975","journal-title":"CLXXXIII. Haloacetylium Ions. J. Am. Chem. Soc."},{"key":"ref_20","doi-asserted-by":"crossref","first-page":"14399","DOI":"10.1021\/acs.joc.4c01783","article-title":"Synthesis and Stabilization of Highly Reactive Haloacetylium Ions","volume":"89","author":"Steiner","year":"2024","journal-title":"J. Org. Chem."},{"key":"ref_21","doi-asserted-by":"crossref","first-page":"3269","DOI":"10.1021\/cr941144x","article-title":"The Chemistry of Highly Fluorinated Carbocations","volume":"96","author":"Krespan","year":"1996","journal-title":"Chem. Rev."},{"key":"ref_22","first-page":"514","article-title":"Aromatic fluoroderivatives XCVIII. Heptafluorophenylacetic acid. Synthesis and some properties","volume":"20","author":"Bardin","year":"1984","journal-title":"J. Org. Chem. USSR"},{"key":"ref_23","doi-asserted-by":"crossref","first-page":"1733","DOI":"10.1246\/cl.1985.1733","article-title":"Carboxylation of alcohols with carbon monoxide supersaturated in strong acid. Facile synthesis of 2,2-bis(4-halophenyl)acetic, -propionic, and related acids","volume":"14","author":"Takahashi","year":"1985","journal-title":"Chem. Lett."},{"key":"ref_24","doi-asserted-by":"crossref","first-page":"11","DOI":"10.1016\/j.jfluchem.2017.07.009","article-title":"Facile Synthesis of 3-(Trifluoromethyl) Adamantane Derivatives","volume":"201","author":"Zhyhadlo","year":"2017","journal-title":"J. Fluor. Chem."},{"key":"ref_25","first-page":"499","article-title":"Reactivity of (fluoroalkyl)adamantanes and their derivatives. III. Synthesis of (fluoroalkyl)adamantanecarboxylic acids","volume":"19","author":"Nazarova","year":"1983","journal-title":"J. Org. Chem. USSR"},{"key":"ref_26","doi-asserted-by":"crossref","first-page":"17682","DOI":"10.1002\/chem.202103391","article-title":"Palladium-Catalyzed Carbonylative Four-Component Synthesis of B-Perfluoroalkyl Amides","volume":"27","author":"Zhang","year":"2021","journal-title":"Chem. A Eur. J."},{"key":"ref_27","doi-asserted-by":"crossref","first-page":"24292","DOI":"10.1002\/anie.202111206","article-title":"Palladium-Catalyzed Perfluoroalkylative Carbonylation of Unactivated Alkenes: Access to B- Perfluoroalkyl Esters","volume":"60","author":"Zhang","year":"2021","journal-title":"Angew. Chem. Intl. Ed."},{"key":"ref_28","doi-asserted-by":"crossref","first-page":"4996","DOI":"10.1021\/jo00016a041","article-title":"A Facile Synthesis of. Alpha.,.Omega.-Dicarboxylic Acids Containing Perfluoroalkylene Groups","volume":"56","author":"Urata","year":"1991","journal-title":"J. Org. Chem."},{"key":"ref_29","doi-asserted-by":"crossref","first-page":"4403","DOI":"10.1016\/S0040-4039(00)99372-9","article-title":"Carbonylation of 1-Perfluoroalkyl-Substituted 2-Iodoalkanes Catalyzed by Transition-Metal Complexes","volume":"30","author":"Urata","year":"1989","journal-title":"Tetrahedron Lett."},{"key":"ref_30","doi-asserted-by":"crossref","first-page":"4407","DOI":"10.1016\/S0040-4039(00)99373-0","article-title":"Palladium-Catalyzed Double Carbonylation of Alkyl Iodides Bearing Perfluoroalkyl Group","volume":"30","author":"Urata","year":"1989","journal-title":"Tetrahedron Lett."},{"key":"ref_31","doi-asserted-by":"crossref","first-page":"1466","DOI":"10.1039\/D0CC07578G","article-title":"Rhodium-Catalyzed Carbonylative Coupling of Alkyl Halides with Thiols: A Radical Process Faster than Easier Nucleophilic Substitution","volume":"57","author":"Ai","year":"2021","journal-title":"Chem. Commun."},{"key":"ref_32","doi-asserted-by":"crossref","first-page":"2481","DOI":"10.1039\/D1SC06581E","article-title":"Ruthenium Pincer Complex-Catalyzed Heterocycle Compatible Alkoxycarbonylation of Alkyl Iodides: Substrate Keeps the Catalyst Active","volume":"13","author":"Ai","year":"2022","journal-title":"Chem. Sci."},{"key":"ref_33","doi-asserted-by":"crossref","first-page":"12238","DOI":"10.1039\/C8CC07470D","article-title":"Development of Efficient Palladium Catalysts for Alkoxycar- bonylation of Alkenes","volume":"54","author":"Liu","year":"2018","journal-title":"Chem. Commun."},{"key":"ref_34","doi-asserted-by":"crossref","first-page":"5235","DOI":"10.1039\/D0CC00650E","article-title":"A General Platinum-Catalyzed Alkoxycarbonylation of Olefins","volume":"56","author":"Yang","year":"2020","journal-title":"Chem. Commun."},{"key":"ref_35","doi-asserted-by":"crossref","first-page":"14365","DOI":"10.1002\/anie.201908451","article-title":"Synthesis of Carboxylic Acids by Palladium-Catalyzed Hydroxycarbonylation","volume":"58","author":"Sang","year":"2019","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_36","doi-asserted-by":"crossref","first-page":"3803","DOI":"10.1021\/jo00169a040","article-title":"Regioselective Hydroesterification and Hydrocarboxylation of 3,3,3-Trifluoropropene and Pentafluorostyrene Catalyzed by Phosphine-Palladium Complex","volume":"48","author":"Fuchikami","year":"1983","journal-title":"J. Org. Chem."},{"key":"ref_37","doi-asserted-by":"crossref","first-page":"17693","DOI":"10.1002\/anie.202105977","article-title":"Asymmetric Alkoxy- and Hydroxy-Carbonylations of Functionalized Alkenes Assisted by B-Carbonyl Groups","volume":"60","author":"Ren","year":"2021","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_38","doi-asserted-by":"crossref","first-page":"4690","DOI":"10.1002\/anie.201813801","article-title":"Pd-Catalyzed Selective Carbonylation of Gem-Difluoroalkenes: A Practical Synthesis of Difluoromethylated Esters","volume":"58","author":"Liu","year":"2019","journal-title":"Angew. Chem. Int. Ed."},{"key":"ref_39","doi-asserted-by":"crossref","first-page":"713","DOI":"10.1021\/acs.oprd.9b00402","article-title":"Pd(OH)2\/C, a Practical and Efficient Catalyst for the Carboxylation of Benzylic Bromides with Carbon Monoxide","volume":"24","author":"Dewez","year":"2020","journal-title":"Org. Process Res. Dev."},{"key":"ref_40","doi-asserted-by":"crossref","first-page":"369","DOI":"10.1055\/s-0039-1690786","article-title":"An Efficient Palladium-Catalysed Aminocarbonylation of Benzyl Chlorides","volume":"31","author":"Oram","year":"2020","journal-title":"Synlett"},{"key":"ref_41","doi-asserted-by":"crossref","first-page":"548","DOI":"10.1177\/1747519819876202","article-title":"An Improved Method for the Synthesis of Phenylacetic Acid Derivatives via Carbonylation","volume":"43","author":"Li","year":"2019","journal-title":"J. Chem. Res."},{"key":"ref_42","doi-asserted-by":"crossref","first-page":"7264","DOI":"10.1016\/j.tet.2013.06.083","article-title":"An Efficiently Cobalt-Catalyzed Carbonylative Approach to Phenylacetic Acid Derivatives","volume":"69","author":"She","year":"2013","journal-title":"Tetrahedron"},{"key":"ref_43","doi-asserted-by":"crossref","first-page":"541","DOI":"10.1039\/b209553j","article-title":"Synthesis of 11C-Amides Using [11C] Carbon Monoxide and in Situ Activated Amines by Palladium- Mediated Carboxaminations","volume":"1","author":"Karimi","year":"2003","journal-title":"Org. Biomol. Chem."},{"key":"ref_44","doi-asserted-by":"crossref","first-page":"2132","DOI":"10.1002\/ejoc.200200586","article-title":"Synthesis of 11C-Labelled Amides by Palladium-Mediated Carboxamination Using [11C]Carbon Monoxide, in Situ Activated Amines and 1,2,2,6,6-Pentamethylpiperidine","volume":"2003","author":"Karimi","year":"2003","journal-title":"Eur. J. Org. Chem."},{"key":"ref_45","doi-asserted-by":"crossref","first-page":"2256","DOI":"10.1039\/B206420K","article-title":"Palladium-Mediated Carboxylation of Aryl Halides (Triflates) or Benzyl Halides Using [13C]\/[11C] Carbon Monoxide with Tetrabutylammonium Hydroxide or Trimethylphenylammonium Hydroxide","volume":"20","author":"Karimi","year":"2002","journal-title":"J. Chem. Soc. Perkin Trans. 1"},{"key":"ref_46","doi-asserted-by":"crossref","first-page":"2541","DOI":"10.1002\/adsc.202100112","article-title":"Palladium-Catalyzed Thiocarbonylation of Benzyl Chlorides with Sulfonyl Chlorides for the Synthesis of Arylacetyl Thioesters","volume":"363","author":"Wang","year":"2021","journal-title":"Adv. Synth. Catal."},{"key":"ref_47","doi-asserted-by":"crossref","first-page":"969","DOI":"10.1039\/C7GC03619A","article-title":"A Sustainable Procedure toward Alkyl Arylacetates: Palladium-Catalysed Direct Carbonylation of Benzyl Alcohols in Organic Carbonates","volume":"20","author":"Li","year":"2018","journal-title":"Green. Chem."},{"key":"ref_48","doi-asserted-by":"crossref","first-page":"5938","DOI":"10.1021\/acs.orglett.8b02631","article-title":"Palladium-Catalyzed Decarboxylative Carbonylative Transformation of Benzyl Aryl Carbonates: Direct Synthesis of Aryl 2-Arylacetates","volume":"20","author":"Xu","year":"2018","journal-title":"Org. Lett."},{"key":"ref_49","doi-asserted-by":"crossref","first-page":"2735","DOI":"10.1016\/0040-4039(91)85071-C","article-title":"The Hydrogenation of Fluoroolefins","volume":"32","author":"Allmendinger","year":"1991","journal-title":"Tetrahedron Lett."},{"key":"ref_50","doi-asserted-by":"crossref","first-page":"3942","DOI":"10.1021\/jo702318d","article-title":"Efficient Synthesis of Trifluoromethyl and Related Trisubstituted Alkene Dipeptide Isosteres by Palladium-Catalyzed Carbonylation of Amino Acid Derived Allylic Carbonates","volume":"73","author":"Inokuchi","year":"2008","journal-title":"J. Org. Chem."},{"key":"ref_51","doi-asserted-by":"crossref","first-page":"79","DOI":"10.1016\/j.ejmech.2017.01.028","article-title":"Synthesis and Biological Evaluation of Fluorinated N-Benzoyl and N -Phenylacetoyl Derivatives of 3-(4-Aminophenyl)-Coumarin-7-O-Sulfamate as Steroid Sulfatase Inhibitors","volume":"128","author":"Rachon","year":"2017","journal-title":"Eur. J. Med. Chem."},{"key":"ref_52","doi-asserted-by":"crossref","first-page":"473","DOI":"10.1016\/j.tet.2009.11.053","article-title":"Synthesis of 2-Aryl-3,3,3-Trifluoropropanoic Acids Using Electrochemical Carboxylation of (1- Bromo-2,2,2-Trifluoroethyl) Arenes and Its Application to the Synthesis of \u03b2,\u03b2,\u03b2-Trifluorinated Non-Steroidal Anti-Inflammatory Drugs","volume":"66","author":"Yamauchi","year":"2010","journal-title":"Tetrahedron"},{"key":"ref_53","doi-asserted-by":"crossref","first-page":"48","DOI":"10.1016\/j.bmcl.2009.11.044","article-title":"Solvent-Free, Microwave Assisted Synthesis of Polyhalo Heterocyclic Ketene Aminals as Novel Anti-Cancer Agents","volume":"20","author":"Yan","year":"2010","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_54","doi-asserted-by":"crossref","first-page":"1832","DOI":"10.1016\/j.bmcl.2011.01.048","article-title":"Maintaining Potent HTLV-I Protease Inhibition without the P3-Cap Moiety in Small Tetrapeptidic Inhibitors","volume":"21","author":"Nguyen","year":"2011","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_55","doi-asserted-by":"crossref","first-page":"2489","DOI":"10.1016\/j.bmc.2005.01.043","article-title":"Fluorinated Phenylcyclopropylamines. Part 4: Effects of Aryl Substituents and Stereochemistry on the Inhibition of Monoamine Oxidases by 1-Aryl-2-Fluoro-Cyclopropylamines","volume":"13","author":"Ye","year":"2005","journal-title":"Bioorg. Med. Chem."},{"key":"ref_56","doi-asserted-by":"crossref","first-page":"3578","DOI":"10.1016\/j.bmcl.2011.04.114","article-title":"Methyl-Monofluorination of Ibuprofen Selectively Increases Its Inhibitory Activity toward Cyclooxygenase-1 Leading to Enhanced Analgesic Activity and Reduced Gastric Damage in Vivo","volume":"21","author":"Su","year":"2011","journal-title":"Bioorg. Med. Chem. Lett."},{"key":"ref_57","doi-asserted-by":"crossref","first-page":"133","DOI":"10.1016\/0014-2999(94)90311-5","article-title":"Pharmacological Properties of R-84760, a Novel \u03ba-Opioid Receptor Agonist","volume":"261","author":"Fujibayashi","year":"1994","journal-title":"Eur. J. Pharmacol."},{"key":"ref_58","doi-asserted-by":"crossref","first-page":"2964","DOI":"10.1016\/j.bmc.2016.05.002","article-title":"Design, Synthesis and Biological Evaluation of Novel Tetrahydroisoquinoline Quaternary Derivatives as Peripheral \u03ba-Opioid Receptor Agonists","volume":"24","author":"Guo","year":"2016","journal-title":"Bioorg. Med. Chem."},{"key":"ref_59","doi-asserted-by":"crossref","first-page":"565","DOI":"10.1038\/aps.2014.145","article-title":"Novel \u03ba-Opioid Receptor Agonist MB-1C-OH Produces Potent Analgesia with Less Depression and Sedation","volume":"36","author":"Zhang","year":"2015","journal-title":"Acta Pharm. Sin."},{"key":"ref_60","doi-asserted-by":"crossref","first-page":"125","DOI":"10.1134\/S2079978016020011","article-title":"Synthesis and Structure-Activity-Relationships of Indan Acid Derivatives as Analgesic and Anti-Inflammatory Agents","volume":"6","author":"Bachar","year":"2016","journal-title":"Ref. J. Chem."},{"key":"ref_61","doi-asserted-by":"crossref","first-page":"3413","DOI":"10.1016\/j.tetlet.2011.03.055","article-title":"Synthesis of Hexahydro [2] Benzopyrano [3,4-c] Pyrroles as Serotonin 5-HT2C Receptor Agonists via Intramolecular Hetero Diels\u2013Alder Reactions","volume":"52","author":"Kiyoi","year":"2011","journal-title":"Tetrahedron Lett."},{"key":"ref_62","doi-asserted-by":"crossref","unstructured":"Im, J., Sterner, E., and Swager, T. (2016). Integrated Gas Sensing System of SWCNT and Cellulose Polymer Concentrator for Benzene, Toluene, and Xylenes. Sensors, 16.","DOI":"10.3390\/s16020183"},{"key":"ref_63","doi-asserted-by":"crossref","first-page":"22943","DOI":"10.1039\/C5RA01020A","article-title":"Self-Assembly and Hydrogelation from Multicomponent Coassembly of Pentafluorobenzyl-Phenylalanine and Pentafluorobenzyl-Diphenylalanine","volume":"5","author":"Hsu","year":"2015","journal-title":"RSC Adv."},{"key":"ref_64","doi-asserted-by":"crossref","first-page":"15079","DOI":"10.1021\/acsami.8b03226","article-title":"Glucosamine-Based Supramolecular Nanotubes for Human Mesenchymal Cell Therapy","volume":"10","author":"Talloj","year":"2018","journal-title":"ACS Appl. Mater. Interfaces"},{"key":"ref_65","doi-asserted-by":"crossref","first-page":"4749","DOI":"10.1021\/cm101193g","article-title":"2-Aminopyrimidine-Silver (I) Based Hybrid Organic Polymers: Self-Assembly and Phase Transitions of a Novel Class of Electronic Material","volume":"22","author":"Stoll","year":"2010","journal-title":"Chem. Mater."},{"key":"ref_66","doi-asserted-by":"crossref","first-page":"572","DOI":"10.1071\/CH21333","article-title":"Monometallic Ln3+ and heterometallic Ln3+\u2013Cd2+ complexes based on pentafluorophenylacetic acid: Efficient control of dimension and luminescent properties","volume":"75","author":"Belousov","year":"2022","journal-title":"Aust. J. Chem."},{"key":"ref_67","first-page":"1863","article-title":"On the hydrolysis of diethyl 2-(perfluorophenyl) malonate","volume":"16","author":"Taydakov","year":"2020","journal-title":"Org. Chem."},{"key":"ref_68","doi-asserted-by":"crossref","first-page":"523","DOI":"10.1134\/S1070428012040100","article-title":"Generation of perfluoro- and 1-chloropolyfluorobenzocycloalken-1-yl cations and their relative stability","volume":"48","author":"Beregovaya","year":"2012","journal-title":"Russ. J. Org. Chem."},{"key":"ref_69","doi-asserted-by":"crossref","first-page":"1010","DOI":"10.1134\/S1070428013070099","article-title":"Reactions of perfluorobenzocycloalkenes with ethyl cyanoacetate and methyllithium and some transformations of the products","volume":"49","author":"Sinyakov","year":"2013","journal-title":"Russ. J. Org. Chem."},{"key":"ref_70","doi-asserted-by":"crossref","first-page":"1797","DOI":"10.1016\/S0040-4020(96)01090-3","article-title":"Transformations of perfluoroxylenes and perfluoro-p-cymene under the action of Zn(Cu)-D-DMF-H2O","volume":"53","author":"Krasnov","year":"1997","journal-title":"Tetrahedron"},{"key":"ref_71","doi-asserted-by":"crossref","first-page":"101","DOI":"10.1016\/S0022-1139(00)82182-X","article-title":"The attempted synthesis of polyparatetrafluorophenylene vinylene via water-soluble and organic solvent-soluble precursor polymers","volume":"50","author":"Brooke","year":"1990","journal-title":"J. Fluor. Chem."},{"key":"ref_72","doi-asserted-by":"crossref","first-page":"2012","DOI":"10.1021\/jo00269a051","article-title":"Metacyclophanes and related compounds. 23. Preparation of fluorinated [2,2]metacyclophanes","volume":"54","author":"Tashiro","year":"1989","journal-title":"J. Org. Chem."},{"key":"ref_73","first-page":"1880","article-title":"Reactions of polyfluoroindans with aluminum chloride and some other Lewis acids. Synthesis of 1,1-dichloropolyfluoroindans","volume":"19","author":"Karpov","year":"1983","journal-title":"J. Org. Chem. USSR"},{"key":"ref_74","doi-asserted-by":"crossref","unstructured":"Barbour, A.K., Buxton, M.W., Coe, P.L., Stephens, R., and Tatlow, J.C. (1961). 173. Aromatic Polyfluoro-Compounds. Part VIII. Pentafluorobenzaldehyde and Related Pentafluorophenyl Ketones and Carboxylic Acids. J. Chem. Soc., 808\u2013817.","DOI":"10.1039\/jr9610000808"},{"key":"ref_75","doi-asserted-by":"crossref","first-page":"780","DOI":"10.1134\/S1070428022060045","article-title":"Reduction of Perfluorinated Benzocycloalkenones and Other Polyfluoroaryl Ketones to Alcohols with LiBH4","volume":"58","author":"Wang","year":"2022","journal-title":"Russ. J. Org. Chem."},{"key":"ref_76","doi-asserted-by":"crossref","first-page":"1652","DOI":"10.1134\/S107042800811016X","article-title":"Reaction of perfluoro-1-methylindan with SiO2-SbF5","volume":"44","author":"Zonov","year":"2008","journal-title":"Russ. J. Org. Chem."},{"key":"ref_77","doi-asserted-by":"crossref","first-page":"1574","DOI":"10.1016\/j.jfluchem.2006.08.006","article-title":"Oxygen replacement by fluorine in carbonyl derivatives of perfluoroaromatic compounds and isomerization of perfluoroindan-1,3-dione to perfluoro-3-methylenephthalide under the action of HF\/SbF5","volume":"127","author":"Zonov","year":"2006","journal-title":"J. Fluor. Chem."},{"key":"ref_78","doi-asserted-by":"crossref","first-page":"1058","DOI":"10.1016\/j.jfluchem.2007.05.020","article-title":"Transformation of Perfluorinated Benzocycloalkenes and Alkylbenzenes to Their Carbonyl Derivatives under the Action of CF3COOH\/SbF5","volume":"128","author":"Zonov","year":"2007","journal-title":"J. Fluor. Chem."},{"key":"ref_79","doi-asserted-by":"crossref","first-page":"317","DOI":"10.1016\/S0022-1139(00)80867-2","article-title":"Fluorine-containing carbocations. IV. The use of salt solutions of stable polyfluorinated \u03b1,\u03b1-difluorobenzyl and \u03b1-fluorodiphenylmethyl cations in antimony pentafluoride in the synthesis of polyfluorinated benzoic acids, benzophenones and diphenyldifluoromethanes","volume":"4","author":"Pozdnyakovich","year":"1974","journal-title":"J. Fluor. Chem."}],"container-title":["Molecules"],"original-title":[],"language":"en","link":[{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/4\/931\/pdf","content-type":"unspecified","content-version":"vor","intended-application":"similarity-checking"}],"deposited":{"date-parts":[[2025,10,9]],"date-time":"2025-10-09T16:36:24Z","timestamp":1760027784000},"score":1,"resource":{"primary":{"URL":"https:\/\/www.mdpi.com\/1420-3049\/30\/4\/931"}},"subtitle":[],"short-title":[],"issued":{"date-parts":[[2025,2,17]]},"references-count":79,"journal-issue":{"issue":"4","published-online":{"date-parts":[[2025,2]]}},"alternative-id":["molecules30040931"],"URL":"https:\/\/doi.org\/10.3390\/molecules30040931","relation":{},"ISSN":["1420-3049"],"issn-type":[{"value":"1420-3049","type":"electronic"}],"subject":[],"published":{"date-parts":[[2025,2,17]]}}}