Synthesis of Sterically Hindered α-Hydroxycarbonyls through Radical-Radical Coupling
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.
Ota, Kenji,Nagao, Kazunori,Ohmiya, Hirohisa
supporting information
p. 4420 - 4425
(2021/05/26)
Ethyl Mandelate as a Convenient New Benzoyl Anion Equivalent
Ethyl mandelate acts as a convenient benzoyl anion equivalent for the formation of alkyl aryl ketones by deprotonation-alkylation followed by flash vacuum pyrolysis.
Aitken, R. Alan,Thomas, Andrew W.
p. 293 - 294
(2007/10/03)
Chemistry of novel compounds with multifunctional carbon structure. VI. Synthetic studies and 19F-nuclear magnetic resonance investigation of novel α,α-disubstituted fluoroacetates
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Takeuchi,Ogura,Ishii,Koizumi
p. 2404 - 2408
(2007/10/02)
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