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Base-Mediated α-<i>gem</i>-Difluoroalkenylations of Aldehydes and Ketones

Yu‐Qing Ni, Dongjie Li, Mei Yan, Yan Jiang, Junlei Zhang, Ke‐Han He, Fei Pan

2023Organic Letters10 citationsDOI

Abstract

Herein, we present a base-mediated nucleophilic substitution reaction of α-trifluoromethylstyrenes with simple silyl enol ethers, enabling the efficient synthesis of carbonyl-substituted gem -difluoroalkenes. The merit of this protocol is exhibited by its mild reaction conditions, broad substrate scope, and scalable preparation. Notably, this method demonstrates its applicability for late-stage functionalization of structurally complex molecules. Moreover, we illustrate that the resulting products can serve as valuable precursors for the synthesis of diverse medicinally relevant compounds.

Topics & Concepts

ChemistrySilylationEnolCombinatorial chemistrySubstrate (aquarium)NucleophileBase (topology)Reaction conditionsSurface modificationScope (computer science)MoleculeOrganic chemistryCatalysisComputer scienceMathematical analysisPhysical chemistryOceanographyGeologyMathematicsProgramming languageFluorine in Organic ChemistryCatalytic C–H Functionalization MethodsCyclopropane Reaction Mechanisms