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

Abstract

A synthetic methodology is reported that functionalizes C60 and C70 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