Electron-Deficient Fluoroarene-Mediated Synthesis of Trifluoromethyl Ketones from Carboxylic Acids
Madhukar S. Said, Nilesh S. Khonde, Pradeep Kumar, Jayant M. Gajbhiye
Abstract
Fluoroarene-mediated trifluoromethylation of carboxylic acids for the synthesis of trifluoromethyl ketones is disclosed. The fluoroarene activates the acid group and generates the fluoride source in situ for the trifluoromethylation reaction. The present protocol is safe and metal-free, operates under mild reaction conditions, and does not require any external additives to generate trifluoromethyl anion. The current transformation provides good functional group tolerance and also delivers 92% and 88% yields of trifluoromethyl ketones in batch and continuous flow, respectively.
Topics & Concepts
TrifluoromethylationTrifluoromethylChemistryFluorideCarboxylic acidFunctional groupMetalCombinatorial chemistryTransformation (genetics)Continuous flowOrganic chemistryInorganic chemistryAlkylGeneBiochemistryPhysicsMechanicsPolymerFluorine in Organic ChemistryInorganic Fluorides and Related CompoundsCyclopropane Reaction Mechanisms