SilverCatalyzed Cascade Carboxylation and Cyclization of Trimethyl(2-methylenebut-3-yn-1-yl)silane Derivatives

Abstract

C–C bond-forming carboxylation and cyclization of trimethyl­(2-methylenebut-3-yn-1-yl)­silane derivatives and carbon dioxide was developed. Silver catalysts and CsF promoted the reaction to afford the corresponding 2-furanone and 2-pyrone derivatives in good-to-high yields. The structure of the 2-furanone was confirmed by single-crystal X-ray crystallography, which revealed that the geometry of the <i>exo</i>-olefin was that of a <i>Z</i>-isomer. When an aromatic ring-substituted alkyne was used, 2-furanone derivatives were selectively obtained via 5-<i>exo-dig</i> cyclization, whereas the reaction of alkyl-substituted alkynes produced 2-pyrone derivatives with high selectivity