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Article Dans Une Revue Organic Letters Année : 2013

Enabling Nucleophilic Substitution Reactions of Activated Alkyl Fluorides through Hydrogen Bonding

Résumé

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$_2$O 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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Chimie
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Dates et versions

hal-01754831 , version 1 (30-03-2018)

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Citer

Pier Alexandre Champagne, Julien Pomarole, Marie-Ève Thérien, Yasmine Benhassine, Samuel Beaulieu, et al.. Enabling Nucleophilic Substitution Reactions of Activated Alkyl Fluorides through Hydrogen Bonding. Organic Letters, 2013, 15, pp.2210 - 2213. ⟨10.1021/ol400765a⟩. ⟨hal-01754831⟩

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