Drastic fluorine effect: complete reversal of the selectivity in the Au-catalyzed hydroalkoxylation reaction of fluorinated haloalkynes
Mélissa Cloutier, Marius Mamone, Jean‐François Paquin
Abstract
The gold-catalyzed hydration reaction of haloalkynes is highly regioselective producing 2-halomethylketones as the sole products. Herein, we document a drastic fluorine effect where the reaction of 1-halo-3,3-difluoroalkynes as substrates leads to a complete reversal of selectivity and produces 3,3-difluoroesters as the unique products.
Topics & Concepts
CatalysisFluorineSelectivityChemistryReaction conditionsMedicinal chemistryCombinatorial chemistryOrganic chemistryFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsCatalytic Alkyne Reactions