1 Ocak 2022 Dergi makalesi Açık Erişim

Erturk, Erkan; Yesil, Tolga A.

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  <identifier identifierType="URL">https://aperta.ulakbim.gov.tr/record/253051</identifier>
  <creators>
    <creator>
      <creatorName>Erturk, Erkan</creatorName>
      <givenName>Erkan</givenName>
      <familyName>Erturk</familyName>
      <affiliation>TUBITAK Marmara Res Ctr, TR-41470 Kocaeli, Turkey</affiliation>
    </creator>
    <creator>
      <creatorName>Yesil, Tolga A.</creatorName>
      <givenName>Tolga A.</givenName>
      <familyName>Yesil</familyName>
    </creator>
  </creators>
  <titles>
    <title>Catalyst-Tuned Electrophilic Chlorination Of Diverse Aromatic Compounds With Sulfuryl Chloride And Regioselective Chlorination Of Phenols With Organocatalysts</title>
  </titles>
  <publisher>Aperta</publisher>
  <publicationYear>2022</publicationYear>
  <dates>
    <date dateType="Issued">2022-01-01</date>
  </dates>
  <resourceType resourceTypeGeneral="Text">Journal article</resourceType>
  <alternateIdentifiers>
    <alternateIdentifier alternateIdentifierType="url">https://aperta.ulakbim.gov.tr/record/253051</alternateIdentifier>
  </alternateIdentifiers>
  <relatedIdentifiers>
    <relatedIdentifier relatedIdentifierType="DOI" relationType="IsIdenticalTo">10.1021/acs.joc.2c00230</relatedIdentifier>
  </relatedIdentifiers>
  <rightsList>
    <rights rightsURI="http://www.opendefinition.org/licenses/cc-by">Creative Commons Attribution</rights>
    <rights rightsURI="info:eu-repo/semantics/openAccess">Open Access</rights>
  </rightsList>
  <descriptions>
    <description descriptionType="Abstract">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 &amp;lt;= 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 &amp;lt;= 99:1 o:p ratio by (S)-diphenylprolinol].</description>
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