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The first umpolung strategy for the cycloacylation of fullerene using a N-heterocyclic carbene organocatalyst is reported. The coupling of 60fullerene with different structural α,β-unsaturated aldehydes efficiently furnishes interesting 60fullerene-fused cyclopentan-1-ones or cyclohex-2-en-1-ones in good to excellent yields. This new reaction displays a wide substrate scope and excellent functional-group tolerance, and diverse substituents such as aryl, heteroaryl, alkenyl, alkyl, and ester can be installed by using the corresponding enals.
Hu et al. (Fri,) studied this question.