Stereochemical outcomes of C-F activation reactions of benzyl fluoride

Neil S. Keddie, Pier Alexandre Champagne, Justine Desroches, Jean-Francois Paquin, David O'Hagan

Research output: Contribution to journalArticlepeer-review

7 Citations (Scopus)

Abstract

In recent years, the highly polar C-F bond has been utilised in activation chemistry despite its low reactivity to traditional nucleophiles, when compared to other C-X halogen bonds. Paquin's group has reported extensive studies on the C-F activation of benzylic fluorides for nucleophilic substitutions and Friedel-Crafts reactions, using a range of hydrogen bond donors such as water, triols or hexafluoroisopropanol (HFIP) as the activators. This study examines the stereointegrity of the C-F activation reaction through the use of an enantiopure isotopomer of benzyl fluoride to identify whether the reaction conditions favour a dissociative (SN1) or associative (SN2) pathway. [2H]-Isotopomer ratios in the reactions were assayed using the Courtieu 2H NMR method in a chiral liquid crystal (poly-γ-benzyl-L-glutamate) matrix and demonstrated that both associative and dissociative pathways operate to varying degrees, according to the nature of the nucleophile and the hydrogen bond donor.

Original languageEnglish
Pages (from-to)106-113
Number of pages8
JournalBeilstein Journal of Organic Chemistry
Volume14
DOIs
Publication statusPublished - 9 Jan 2018

Keywords

  • Benzylic fluorides
  • C-F activation
  • Chiral liquid crystal
  • 2H NMR
  • PBLG
  • stereochemistry

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