Copper-mediated synthesis of fullerooxazoles from [60]fullerene and N-hydroxybenzimidoyl cyanides.

A novel and efficient copper-mediated [3 + 2] heteroannulation reaction of [60]fullerene with N-hydroxybenzimidoyl cyanides has been developed for the synthesis of fullerooxazoles. A possible reaction mechanism involving unique C-CN and N-OH bond cleavages and subsequent C-OH bond formation for N-hydroxybenzimidoyl cyanides is proposed to explain the generation of fullerooxazoles. In addition, the formed fullerooxazoles can be further electrochemically transformed into amidated 1,2-hydrofullerenes.