Friedel-crafts reaction of benzyl fluorides: Selective activation of C-f bonds as enabled by hydrogen bonding

Pier Alexandre Champagne, Yasmine Benhassine, Justine Desroches, Jean François Paquin

Research output: Contribution to journalArticlepeer-review

128 Scopus citations

Abstract

A Friedel-Crafts benzylation of arenes with benzyl fluorides has been developed. The reaction produces 1,1-diaryl alkanes in good yield under mild conditions without the need for a transition metal or a strong Lewis acid. A mechanism involving activation of the C-F bond through hydrogen bonding is proposed. This mode of activation enables the selective reaction of benzylic C-F bonds in the presence of other benzylic leaving groups.

Original languageEnglish (US)
Pages (from-to)13835-13839
Number of pages5
JournalAngewandte Chemie - International Edition
Volume53
Issue number50
DOIs
StatePublished - Oct 10 2014
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Keywords

  • Arenes
  • Benzyl fluorides
  • C-F activation
  • Friedel-Crafts reaction
  • Hydrogen bonds

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