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

76 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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Chlorination
Halogenation
Catalysis
Chlorides
Alcohols
Trifluoroethanol
Benzene
Discrete Fourier transforms
Metals
Derivatives
Oxidation
Catalysts

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

Electrophilic aromatic chlorination and haloperoxidation of chloride catalyzed by polyfluorinated alcohols : A new manifestation of template catalysis. / Ben-Daniel, Revital; De Visser, Samuël P.; Shaik, Sason; Neumann, Ronny.

In: Journal of the American Chemical Society, Vol. 125, No. 40, 08.10.2003, p. 12116-12117.

Research output: Contribution to journalArticle

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