4.8 Article

Visible Light-Promoted Friedel-Crafts-Type Chloroacylation of Alkenes to β-Chloroketones

Journal

ORGANIC LETTERS
Volume 22, Issue 8, Pages 3018-3022

Publisher

AMER CHEMICAL SOC
DOI: 10.1021/acs.orglett.0c00788

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Funding

  1. National Research Foundation of Korea (NRF) - Korean government (MSICT) [NRF-2015R1A5A1008958, NRF-2019R1A2C2089953]

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The photoredox chloroacylation of alkenes has been developed as a substitute for the Friedel-Crafts acylation of alkenes to beta-chloroketones. The direct generation of acyl radical species from acid chlorides under the photoredox conditions allows the formation of beta-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.

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