Addition of Tetrahydrofuran to [60]Fullerene through C−H Bond Activation Induced by Arylzinc Reagents

The reaction of [60]fullerene with an arylzinc halide in a mixture of THF and DMF produces a mono(2-tetrahydrofuranyl) adduct of [60]fullerene C60(C4H7O)H instead of the expected arylated fullerene. The reaction involves a C−H bond activation at the 2-position of THF that probably takes place through a radical mechanism. In the presence of a copper(I) complex, the reaction does not stop at the stage of mono-addition, with the aryl group of the zinc reagent adding four times regioselectively to the mono(2-tetrahydrofuranyl) adduct to produce a penta-adduct C60Ar4(C4H7O)H. This product can be converted further to the corresponding buckyferrocene Fe[C60Ar4(C4H7O)]Cp and its derivatives.