Copper-Catalyzed Reaction of C60 with Tertiary Amines for the Preparation of Spiro-Linked Methanofullerenes and Fullerenoalkanals.

CuI-catalyzed reaction of C60 with tertiary amines by using air as the sole oxidant has been developed. Spiro-linked methanofullerenes bearing cyclic amides and fullerenoalkanals can be obtained selectively using the cyclic and acyclic amines as starting materials, respectively. The reactions show a wide functional group tolerance. In addition, four ([6,6]-phenyl-C61-butyric acid methyl ester) analogues can be easily prepared through the developed method.