Enabling nucleophilic substitution reactions of activated alkyl fluorides through hydrogen bonding

Pier Alexandre Champagne, Julien Pomarole, Marie Ève Thérien, Yasmine Benhassine, Samuel Beaulieu, Claude Y. Legault, Jean François Paquin

Research output: Contribution to journalArticlepeer-review

58 Scopus citations

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···H 2O 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.

Original languageEnglish (US)
Pages (from-to)2210-2213
Number of pages4
JournalOrganic Letters
Volume15
Issue number9
DOIs
StatePublished - May 3 2013
Externally publishedYes

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

Fingerprint

Dive into the research topics of 'Enabling nucleophilic substitution reactions of activated alkyl fluorides through hydrogen bonding'. Together they form a unique fingerprint.

Cite this