Triol-promoted activation of C-F bonds: Amination of benzylic fluorides under highly concentrated conditions mediated by 1,1,1-tris(hydroxymethyl) propane

Pier Alexandre Champagne, Alexandre Saint-Martin, Mélina Drouin, Jean François Paquin

Research output: Contribution to journalArticlepeer-review

20 Scopus citations

Abstract

Activation of the C-F bond of benzylic fluorides was achieved using 1,1,1-tris(hydroxymethyl)propane (2) as a hydrogen bonddonating agent. Investigations demonstrated that hydrogen bond-donating solvents are promoting the activation and hydrogen bondaccepting ones are hindering it. However, the reaction is best run under highly concentrated conditions, where solvents cannot interfere with the interaction between the organofluorine compound and the triol. Various benzylic fluorides react with secondary amines or anilines to form benzylic amines in good yields.

Original languageEnglish (US)
Pages (from-to)2451-2456
Number of pages6
JournalBeilstein Journal of Organic Chemistry
Volume9
DOIs
StatePublished - Nov 13 2013
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Organic Chemistry

Keywords

  • C-F bond activation
  • Highly concentrated conditions
  • Hydrogen bond
  • Nucleophilic substitution
  • Organofluorine
  • Triol

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