1 Ocak 2022 Dergi makalesi Açık Erişim

Erturk, Erkan; Yesil, Tolga A.

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        "affiliation": "TUBITAK Marmara Res Ctr, TR-41470 Kocaeli, Turkey", 
        "name": "Erturk, Erkan"
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        "name": "Yesil, Tolga A."
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    "description": "In 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].", 
    "doi": "10.1021/acs.joc.2c00230", 
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    "journal": {
      "issue": "19", 
      "pages": "12558-12573", 
      "title": "JOURNAL OF ORGANIC CHEMISTRY", 
      "volume": "87"
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    "publication_date": "2022-01-01", 
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    "title": "Catalyst-Tuned Electrophilic Chlorination of Diverse Aromatic Compounds with Sulfuryl Chloride and Regioselective Chlorination of Phenols with Organocatalysts"
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