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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

2021Advanced Synthesis & Catalysis17 citationsDOI

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