Synthesis of alkyl 2,5-dihydro-5-oxofuran-2-carboxylates via palladium-catalyzed carbonylative cyclization of β-bromovinyl aldehydes in alcohols

β-Bromovinyl aldehydes reacts with carbon monoxide and alcohols at 125 °C in the presence of a catalytic amount of a palladium catalyst along with a base to give the corresponding carbonylative cyclized alkyl 2,5-dihydro-5-oxofuran-2-carboxylates in good yields. A reaction pathway involving intramolecular addition of acylpalladium to formyl group is proposed as a key step of this catalytic process.

Graphical abstractβ-Bromovinyl aldehydes are carbonylatively cyclized under carbon monoxide pressure in alcohols at 125 °C in the presence of a catalytic amount of a palladium catalyst along with a base to give the corresponding alkyl 2,5-dihydro-5-oxofuran-2-carboxylates in good yields.Figure optionsDownload full-size imageDownload as PowerPoint slide