Single-step synthesis of pentaaryl-monohydro[60]fullerenes through fivefold addition of organocopper reagent to C60

The reaction of an organocopper reagent (ArMgBr/CuBr·SMe2) with C60 was optimized for the fivefold addition forming a novel Cp-type ligand precursor 1,4,11,15,30-pentaaryl-2-hydro[60]fullerene (C60Ar5H, 1), where Ar stands for Ph, 4-CF3C6H4, 4-MeOC6H4, 4-ClC6H4, 4-BuC6H4, 4-PhC6H4, and 1-naphthyl groups. Under the optimized conditions, a large quantity (8.90 g) of C60Ph5H has been synthesized in a single operation.