1 Ocak 2022 Dergi makalesi Açık Erişim

Erturk, Erkan; Yesil, Tolga A.

Citation Style Language JSON

{
  "DOI": "10.1021/acs.joc.2c00230", 
  "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 <= 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].", 
  "author": [
    {
      "family": "Erturk", 
      "given": " Erkan"
    }, 
    {
      "family": "Yesil", 
      "given": " Tolga A."
    }
  ], 
  "container_title": "JOURNAL OF ORGANIC CHEMISTRY", 
  "id": "253051", 
  "issue": "19", 
  "issued": {
    "date-parts": [
      [
        2022, 
        1, 
        1
      ]
    ]
  }, 
  "page": "12558-12573", 
  "title": "Catalyst-Tuned Electrophilic Chlorination of Diverse Aromatic Compounds with Sulfuryl Chloride and Regioselective Chlorination of Phenols with Organocatalysts", 
  "type": "article-journal", 
  "volume": "87"
}