Synthesis of Fused Dihydroazepine Derivatives of Fullerenes by a Rh-Catalyzed Cascade Process

A synthetic methodology is reported that functionalizes C-60 and C-70 fullerenes with dihydroazepine rings by a cascade reaction encompassing a rhodium-catalyzed cycloisomerization of 1,5-bisallenes and a [4+2] cycloaddition. This transition metal-catalyzed cascade reaction provides a versatile and step-economical approach to the synthesis of 6,7-membered polyheterocyclic fullerene adducts. Electrochemical characterization of the products obtained ventures their application in organic and perovskite photovoltaic devices.

Automated summary

A synthetic methodology for functionalizing C-60 and C-70 fullerenes by cascading reactions has been reported. The resulting polyheterocyclic fullerene adducts can be potentially used in organic and perovskite photovoltaic devices.