Mild conversion of beta-diketones and beta-ketoesters to carboxylic acids.
A mild protocol for the conversion of beta-ketoesters and beta-diketones to carboxylic acids with use of CAN in CH3CN is described. The method is compatible with a number of functional groups, and can generate carboxylic acids under neutral conditions at room temperature. The reaction is fast and general, providing an alternative method to the commonly used malonic ester acid preparation. Initial mechanistic studies show that initial oxidation of the enol form of the beta-dicarbonyl initiates the reaction. The presence of nitrate as an oxidant ligand or as an additive is critical for success of the reaction.
Zhang
Yang
Y
Department of Chemistry, Lehigh University, Bethlehem, Pennsylvania 18015, USA.
Jiao
Jingliang
J
Flowers
Robert A
RA
D002264:Carboxylic Acids / Q000138:chemical synthesis*; D004952:Esters / Q000737:chemistry*; D006863:Hydrogen-Ion Concentration; D007202:Indicators and Reagents; D007659:Ketones / Q000737:chemistry*; D008722:Methods; D009566:Nitrates / Q000737:chemistry; D013696:Temperature
D002264:Carboxylic Acids; D004952:Esters; D007202:Indicators and Reagents; D007659:Ketones; D009566:Nitrates