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.
Download full-text PDF |
Source |
---|---|
http://dx.doi.org/10.1021/acs.orglett.1c01358 | DOI Listing |
Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!