Palladium-catalyzed synthesis of [60]fullerene-fused benzofurans via heteroannulation of phenols.

Palladium-catalyzed heteroannulation of [60]fullerene with phenols has been developed as a practical and efficient protocol for the one-pot synthesis of various [60]fullerene-fused benzofurans. A possible reaction mechanism is proposed to explain the formation of C60-fused benzofurans. A novel 1,2,3,16-adduct is obtained through further reaction of the electrochemically generated dianionic fullerobenzofuran with benzyl bromide.