Categories: C-C Bond Formation > Oxygen-containing molecules > Carboxyl derivatives >

Synthesis of α-keto carboxylic acids, esters and amides

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Recent Literature

Photoirradiation enables an intermolecular carbon-carbon bond formation between acylsilanes and carbon dioxide to provide α-ketocarboxylic derivatives in good yields under catalyst-free conditions.
Z. Fan, Y. Yi, S. Chen, C. Xi, Org. Lett., 2021, 23, 2303-2307.

A photoredox/NHC cocatalyzed decarboxylative acylation of oxamic acid with acyl fluoride provides a variety of useful α-keto amides, including sterically congested ones, under mild conditions via a two-component radical cross-coupling reaction.
H.-B. Yang, X.-F. Jin, H. Y. Jiang, W. Luo, Org. Lett., 2023, 25, 1829-1833.

A general Pd-catalyzed double carbonylation of aryl iodides with secondary or primary amines provides α-ketoamides in high yields with excellent chemoselectivities at atmospheric CO pressure. This transformation proceeds successfully even at room temperature and in the absence of any ligand and additive.
H. Du, Q. Ruan, M. Qi, W. Han, J. Org. Chem., 2015, 80, 7816-7823.