Faster initiation in the Friedel-Crafts reaction of benzyl fluorides using trifluoroacetic acid as activator

Rémy Hemelaere, Pier Alexandre Champagne, Justine Desroches, Jean François Paquin

Research output: Contribution to journalArticlepeer-review

18 Scopus citations

Abstract

We report that the addition of a catalytic amount of trifluoroacetic acid (TFA) shortens the induction period associated with the 1,1,1,3,3,3-hexafluoroisopropoanol (HFIP)-promoted Friedel-Crafts reaction of benzylic fluorides. This faster initiation is due to TFA's strong hydrogen-bond donation capability, not its Brønsted acidity. The improved reaction conditions were applied to a set of substrates, demonstrating how they could improve yields and reliability of this transformation.

Original languageEnglish (US)
Pages (from-to)1-6
Number of pages6
JournalJournal of Fluorine Chemistry
Volume190
DOIs
StatePublished - 2016
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Environmental Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

Keywords

  • Benzyl fluorides
  • C-F bond activation
  • Friedel-Crafts alkylation
  • Hydrogen-bonding

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