Regiospecific synthesis of 3,4-disubstituted furans

Abstract

Tris[4-(substituted)furan-3-yl]boroxines, prepared from the corresponding 4-(substituted)-3-(trimethylsilyl)furan, were converted successfully through palladium-catalyzed cross-coupling reactions with tri-n-butylstannyl chloride to 4-(substituted)-3-(tri-n-butylstannyl)furans, which underwent further palladium-catalyzed reactions with organohalides to afford 3,4-disubstituted furans. Oxidation of tris[4-(substituted)furan-3-yl]boroxines generated the corresponding 4-substituted-3(2H)furanones.