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Enabling Nucleophilic Substitution Reactions of Activated Alkyl Fluorides through Hydrogen Bonding

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journal contribution
posted on 2016-02-19, 10:15 authored by Pier Alexandre Champagne, Julien Pomarole, Marie-Ève Thérien, Yasmine Benhassine, Samuel Beaulieu, Claude Y. Legault, Jean-François Paquin
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.