1 Ocak 2022 Dergi makalesi Açık Erişim

Erturk, Erkan; Yesil, Tolga A.

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  <dc:creator>Erturk, Erkan</dc:creator>
  <dc:creator>Yesil, Tolga A.</dc:creator>
  <dc:date>2022-01-01</dc:date>
  <dc: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 &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 &lt;= 99:1 o:p ratio by (S)-diphenylprolinol].</dc:description>
  <dc:identifier>https://aperta.ulakbim.gov.trrecord/253051</dc:identifier>
  <dc:identifier>oai:aperta.ulakbim.gov.tr:253051</dc:identifier>
  <dc:rights>info:eu-repo/semantics/openAccess</dc:rights>
  <dc:rights>http://www.opendefinition.org/licenses/cc-by</dc:rights>
  <dc:source>JOURNAL OF ORGANIC CHEMISTRY 87(19) 12558-12573</dc:source>
  <dc:title>Catalyst-Tuned Electrophilic Chlorination of Diverse Aromatic Compounds with Sulfuryl Chloride and Regioselective Chlorination of Phenols with Organocatalysts</dc:title>
  <dc:type>info:eu-repo/semantics/article</dc:type>
  <dc:type>publication-article</dc:type>
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