Oxidative Coupling of Carbon Acid Compounds by Means of Ag₂O

Abstract

Abstract Transition-metal catalyzed coupling of carbanions by means of transition metal compounds has constituted a convenient method of the carbon-carbon bond formation in organic synthesis.1 Recently, CuCl2-promoted coupling of lithium enolates of ketones2 and esters3 has been reported, which provides new routes to 1,4-diketones and succinate derivatives, respectively. Now we found that some carbon acids, such as acylacetate and monosubstituted malonate, were readily oxidatively dimerized by Ag2O without intervention of their carbanions in dimethyl sulfoxide (DMSO) according to eq. 1.