A [3 + 2]-annulation approach to tetrasubstituted furans from MBH-carbonates of acetylenic aldehydes via sequential substitution/cycloisomerization

Abstract

A novel metal-free approach to construct the tetrasubstituted furans from Morita–Baylis–Hillman (MBH)-carbonates of acetylenic aldehydes has been developed. This strategy involves the cascade nucleophilic substitution/5-exo-dig-cycloisomerization of MBH-carbonates with 1,3-dicarbonyl compounds to give uniquely substituted 2-furan-3-yl acrylates. Additionally, the obtained furan adducts open a new entry to naphthofurans through palladium-catalyzed decarboxylative benzannulation.