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Enabling nucleophilic substitution reactions of activated alkyl fluorides through hydrogen bonding.

Authors
  • Champagne, Pier Alexandre
  • Pomarole, Julien
  • Thérien, Marie-Ève
  • Benhassine, Yasmine
  • Beaulieu, Samuel
  • Legault, Claude Y
  • Paquin, Jean-François
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
May 03, 2013
Volume
15
Issue
9
Pages
2210–2213
Identifiers
DOI: 10.1021/ol400765a
PMID: 23614350
Source
Medline
License
Unknown

Abstract

It was discovered that the presence of water as a cosolvent enables the reaction of activated alkyl fluorides for bimolecular nucleophilic substitution reactions. DFT calculations show that activation proceeds through stabilization of the transition structure by a stronger F···H2O interaction and diminishing C-F bond elongation, and not simple transition state electrostatic stabilization. Overall, the findings put forward a distinct strategy for C-F bond activation through H-bonding.

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