Convergent Synthesis of a Polyfunctionalized Fullerene by Regioselective Five-Fold Addition of a Functionalized Organocopper Reagent to C60

[reaction: see text] A method for one-step preparation of polyfunctionalized fullerene derivatives by regioselective penta-addition of an organocopper reagent is described. A functionalized aryl iodide is first converted to the corresponding Grignard reagent and then to a copper reagent and finally is allowed to react with C(60). The method allows introduction of five functional groups to the C(60) skeleton in a convergent manner. The shuttlecock-like molecules crystallize into a columnar packing structure.