Visible‐Light‐Promoted Oxy‐difluoroalkylation of Aryl Alkynes for the Synthesis of <i>β</i>‐Fluoroenones and <i>α</i>‐Difluoroalkyl Ketones
Zhong Zhang, Xiangqian Li, Dayong Shi
Abstract
Abstract A method for the selective synthesis of ( E )‐ β ‐fluoroenones and α ‐difluoroalkyl ketones have been achieved. By employing water as oxygen source, potassium carbonate as base, tetrasubstituted β ‐fluoroenones could be regio‐ and stereoselectively synthesized by oxy‐difluoroalkylation of alkynes under visible light irradiated with moderate to good yields. α‐Difluoroalkyl ketones could be obtained while using phenylpyridine as base. This transformation features mild condition, wide functional tolerance and step economy. The large‐scale transformations and further derivatization show its potential application in organic synthesis. magnified image
Topics & Concepts
ChemistryArylDerivatizationPotassium carbonateBase (topology)Visible spectrumOrganic synthesisCombinatorial chemistryCarbonateTransformation (genetics)PotassiumCatalysisPhotochemistryOrganic chemistryAlkylHigh-performance liquid chromatographyOptoelectronicsMathematicsBiochemistryGeneMathematical analysisPhysicsFluorine in Organic ChemistryRadical Photochemical ReactionsCatalytic C–H Functionalization Methods