Electrophilic aromatic chlorination and haloperoxidation of chloride catalyzed by polyfluorinated alcohols: A new manifestation of template catalysis

Revital Ben-Daniel, Samuël P. De Visser, Sason Shaik, Ronny Neumann

Research output: Contribution to journalArticle

79 Citations (Scopus)

Abstract

We have demonstrated that a polyfluorinated alcohol, 2,2,2-trifluoroethanol, solvent enables haloperoxidase type activity and the oxychlorination of arenes (benzene and its alkylated derivatives) without a metal catalyst. The polyfluorinated alcohol has a dual function; it catalyzes electrophilic chlorination of less reactive arenes by several orders of magnitude and oxidation of chloride at lower H+ concentrations. DFT calculations show that a complementary charge template in the transition state explains the catalysis of the electrophilic chlorination.

Original languageEnglish
Pages (from-to)12116-12117
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number40
DOIs
Publication statusPublished - Oct 8 2003

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ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

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