Related Experiment Video
Updated: Dec 25, 2025

Light-driven Enzymatic Decarboxylation
Published on: May 22, 2016
Visible Light-Promoted Friedel-Crafts-Type Chloroacylation of Alkenes to β-Chloroketones
Dilip V Patil1, Hun Young Kim1, Kyungsoo Oh1
1Center for Metareceptome Research, Graduate School of Pharmaceutical Sciences, Chung-Ang University, 84 Heukseok-ro, Dongjak, Seoul 06974, Republic of Korea.
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.
More Related Videos
Related Concept Videos
Electrophilic Aromatic Substitution: Friedel–Crafts Alkylation of Benzene
Limitations of Friedel–Crafts Reactions
Electrophilic Aromatic Substitution: Friedel–Crafts Acylation of Benzene
Halogenation of Alkenes
Consider the bromination of cyclopentene. Molecular bromine is polarized in the proximity of the π electrons of cyclopentene. An electrophilic bromine atom adds across the double bond, forming a cyclic bromonium ion intermediate.
Radical Substitution: Allylic Chlorination
Alkynes to Aldehydes and Ketones: Hydroboration-Oxidation
One of the convenient methods for the preparation of aldehydes and ketones is via hydration of alkynes. Hydroboration-oxidation of alkynes is an indirect hydration reaction in which an alkyne is treated with borane followed by oxidation with alkaline peroxide to form an enol that rapidly converts into an aldehyde or a ketone. Terminal alkynes form aldehydes, whereas internal alkynes give ketones as the final product.

