Angewandte Chemie International Edition · 2014 · 190 citations · 62 references
Natural SciencesChemical EngineeringChemistryCatalysisOrganic ChemistryReaction EngineeringCarboxylic AcidsCarboxylic DerivativesEmulsion FormationEmulsion FormulationSurfactantsActivation Of Carboxylic AcidsAliphatic Carboxylic AcidsEmulsion BehaviorMild Reaction ConditionsOil-in-water Emulsion Systems
A silver-catalyzed decarboxylative trifluoromethylthiolation of secondary and tertiary carboxylic acids under mild conditions tolerates a wide range of functional groups. The reaction was dramatically accelerated by its performance in an aqueous emulsion, which was formed by the addition of sodium dodecyl sulfate to water. It was proposed that the radical, which was generated from the silver-catalyzed decarboxylation in the "oil-in-water" droplets, could easily react with the trifluoromethylthiolating reagent to form the product.
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