Categories: C=O Bond Formation > Synthesis of Ketones
Synthesis of α-keto carboxylic acids, esters and amides
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Recent Literature
Natural sunlight and air are enable an efficient oxidation of α-aryl halogen
derivatives to the corresponding α-aryl carbonyl compounds at room temperature
through the combination of photocatalysis and organocatalysis. A plausible
mechanism was proposed on the basis of the mechanistic studies.
Y. Su, L. Zhang, N. Jiao, Org. Lett., 2011,
13, 2168-2171.
The reaction of aryl diazoacetates with H2O and diethyl
azodicarboxylate (DEAD) catalyzed by dirhodium acetate gives aryl α-keto esters
in high yields.
Z. Guo, H. Huang, Q. Fu, W. Hu, Synlett, 2006,
2486-2488.
A Cu-catalyzed oxidative amidation-diketonization reaction of terminal alkynes
leads to α-ketoamides. In this copper-catalyzed radical process, O2
not only participates as the ideal oxidant but also undergoes dioxygen
activation under ambient conditions.
C. Zhang, N. Jiao, J. Am. Chem. Soc., 2010,
132, 28-29.
A transition-metal-free oxidative C-C bond cleavage process for a broad range of
ester and dicarbonyl compounds involves carbanion addition to nitrosobenzene and
proceeds via fragmentation of a previously unobserved oxazetidin-4-one
heterocycle.
J. N. Payette, H. Yamamoto, J. Am. Chem. Soc., 2008,
130, 12276-12278.
