Tetrasubstituted
furans were efficiently synthesized from Fe(OAc)2-catalyzed
C–H/C–H cross-dehydrogenative-coupling (CDC) reactions
of activated carbonyl methylenes with S,S-functionalized internal olefins, that is, α-oxo ketene dithioacetals
and analogues, under oxidative conditions. β-Ketoesters, 1,3-dicarbonyls,
β-keto nitrile, and amide derivatives were used as the coupling
partners. The resultant alkylthio- and carbonyl-functionalized furans
could be further transformed to diverse arylated furan derivatives
and furan-fused N-heterocycles, respectively. The
control experiments have revealed a radical reaction pathway.