Catalyst-Tuned Electrophilic Chlorination of Diverse Aromatic Compounds with Sulfuryl Chloride and Regioselective Chlorination of Phenols with Organocatalysts

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dc.authoridYESIL, Tolga Acar/0000-0001-5983-8447
dc.authoridErturk, Erkan/0000-0001-5746-5683
dc.contributor.authorErturk, Erkan
dc.contributor.authorYesil, Tolga A.
dc.date.accessioned2025-03-23T19:35:52Z
dc.date.available2025-03-23T19:35:52Z
dc.date.issued2022
dc.departmentSinop Üniversitesi
dc.description.abstractIn this work, we demonstrate that diverse aromatic compounds can be selectively chlorinated through the fine-tuning of the reactivity of sulfuryl chloride (SO2Cl2) by organocatalysts. Acetonitrile has been identified to activate SO2Cl2 most strongly, thus enabling even chlorination of p-xylene with high yields. 1,4-Dioxane effects chlorination of oxidation-labile aromatic compounds such as p-cresol and 2-naphthol with high yields, 95% and 85%, respectively. An array of potential catalysts has been screened for ortho- and para-selective chlorination of phenols. Thus, we found that acetonitrile, (S)-BINAPO (5 mol %), and diisopropyl ether (4.00 equiv) can catalyze the chlorination of phenols in a para-selective manner (with <= 4:96 o:p ratio), whereas Nagasawa's bis-thiourea (1 mol %), phenyl boronic acid (5 mol %), and (S)-diphenylprolinol (1 mol %) exhibit high ortho selectivity [with <= 99:1 o:p ratio by (S)-diphenylprolinol].
dc.identifier.doi10.1021/acs.joc.2c00230
dc.identifier.endpage12573
dc.identifier.issn0022-3263
dc.identifier.issn1520-6904
dc.identifier.issue19
dc.identifier.pmid36137270
dc.identifier.scopusqualityQ2
dc.identifier.startpage12558
dc.identifier.urihttps://doi.org/10.1021/acs.joc.2c00230
dc.identifier.urihttps://hdl.handle.net/11486/5953
dc.identifier.volume87
dc.identifier.wosWOS:000861630800001
dc.identifier.wosqualityQ1
dc.indekslendigikaynakWeb of Science
dc.indekslendigikaynakPubMed
dc.language.isoen
dc.publisherAmer Chemical Soc
dc.relation.ispartofJournal of Organic Chemistry
dc.relation.publicationcategoryMakale - Uluslararası Hakemli Dergi - Kurum Öğretim Elemanı
dc.rightsinfo:eu-repo/semantics/closedAccess
dc.snmzKA_WOS_20250323
dc.subjectLewis-Base Catalysis
dc.subjectSelective Chlorination
dc.subjectCarbonyl-Compounds
dc.subjectAlpha-Arylation
dc.subjectBronsted Acid
dc.subjectChemistry
dc.subjectHalogenation
dc.subjectReactivity
dc.subjectBiology
dc.subjectKetones
dc.titleCatalyst-Tuned Electrophilic Chlorination of Diverse Aromatic Compounds with Sulfuryl Chloride and Regioselective Chlorination of Phenols with Organocatalysts
dc.typeArticle

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