Copper-Promoted Synthesis of 2-Fulleropyrrolines via Heteroannulation of [60]Fullerene with α-Amino Ketones.

A Cu(OAc)2-promoted heteroannulation of [60]fullerene with α-amino ketones has been exploited for the efficient synthesis of 2-fulleropyrrolines containing a trisubstituted or tetrasubstituted C═C bond via the formation of C-C and C-N bonds. Mechanistic study indicates that a radical process should be involved in this transformation. Furthermore, theoretical computations show that the process via the attack of the carbon radical generated from the employed α-amino ketone to [60]fullerene should be the preferred pathway. The electrochemical properties of the synthesized 2-fulleropyrrolines have also been investigated.