Synthesis of Sterically Hindered α-Hydroxycarbonyls through Radical-Radical Coupling.

Org Lett

Division of Pharmaceutical Sciences, Graduate School of Medical Sciences, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan.

Published: June 2021

AI Article Synopsis

  • The text discusses a new method for creating challenging α-hydroxy carbonyl compounds using radical-radical coupling techniques.* -
  • It utilizes organic photoredox catalysis to convert specific carboxylic acids and α-ketocarbonyls into alkyl and ketyl radicals that can couple selectively.* -
  • This approach supports the use of different types of carboxylic acids, allowing for the incorporation of various alkyl groups into ketone structures under mild conditions.*

Article Abstract

We describe a synthetic approach to sterically hindered α-hydroxy carbonyl compounds through radical-radical coupling. An organic photoredox catalysis reaction converts an aliphatic carboxylic acid and α-ketocarbonyl to a transient alkyl radical and a persistent ketyl radical, respectively, which couple selectively based on the persistent radical effect. This protocol allows the use of primary, secondary, and tertiary aliphatic carboxylic acids to introduce various alkyl substituents onto ketone moieties of α-ketocarbonyls under mild reaction conditions.

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Source
http://dx.doi.org/10.1021/acs.orglett.1c01358DOI Listing

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