Visible Light-Promoted Friedel–Crafts-Type Chloroacylation of Alkenes to β-Chloroketones
Dilip V. Patil, Hun Young Kim, Kyungsoo Oh
Abstract
The photoredox chloroacylation of alkenes has been developed as a substitute for the Friedel–Crafts acylation of alkenes to β-chloroketones. The direct generation of acyl radical species from acid chlorides under the photoredox conditions allows the formation of β-chloroketones without dehydrochlorination with the help of KHCO3. The synthetic utility of the current method is demonstrated in the one-pot synthesis of dihydroisoxazole, dihydropyrazole, and dihydropyrimidine-2-thione in 1 mmol scale.
Topics & Concepts
ChemistryFriedel–Crafts reactionAcylationAlkenePhotoredox catalysisOrganic chemistryCombinatorial chemistryCatalysisPhotocatalysisRadical Photochemical ReactionsFluorine in Organic ChemistryOxidative Organic Chemistry Reactions