Tunable Copper-Catalyzed Reaction of C60 with 2-Ethoxycarbonylacetamides and Subsequent BF3·Et2O-Mediated Isomerization of the Generated Dihydrofuran-Fused Fullerenes to Fulleropyrrolidinones.

A tunable copper-catalyzed reaction of C60 with 2-ethoxycarbonylacetamides using air as the oxidant has been explored, which selectively affords methanofullerenes (2) and dihydrofuran-fused fullerenes (3) under the CuI/DMAP and CuCl/NMI catalytic systems, respectively. Furthermore, the generated dihydrofuran-fused fullerenes could be transformed to fulleropyrrolidinones (4 and 5) upon treatment with BF3·Et2O.

Reaction of C60 with Inactive Secondary Amines and Aldehydes and the Cu(OAc)2-Promoted Regioselective Intramolecular C-H Functionalization of the Generated Fulleropyrrolidines.

The thermal reaction of C60 with aromatic aldehydes and inactive secondary amines for the stereoselective synthesis of trans-1,2,5-trisubstituted fulleropyrrolidines has been developed. Moreover, when an o-hydroxyl group was located at the phenyl ring of the generated fulleropyrrolidines, the Cu(OAc)2-promoted regioselective intramolecular C-O coupling reaction occurred to generate unique tricycle-fused fullerene derivatives.

Cu(OAc)2-Mediated Reaction of C60 with Ureas for the Preparation of Fulleroimidazolidinones.

The Cu(OAc)2-mediated intermolecular diamination reaction of C60 with ureas allows the concise and efficient preparation of fulleroimidazolidinones involving the cleavage of two N-H bonds and formation of two C-N bonds. Both dialkylated and diarylated fulleroimidazolidinones can be synthesized using this method.