Functionalization reactions lead to fullerene derivatives with substantially improved solubility and modified chemical and physical properties, increasing their potential applications in many different fields. Due to the formation of relatively stable cycloadducts in good yields and easy access of reactants, cycloadditions have been one of the most intensively used reactions to prepare fullerene derivatives. This talk will describe two new cycloaddition reactions on fullerenes and metallofullerenes studied in our group. In the first story, an oxidative [4+2] reaction of aromatic diamines on C60 and C70 will be covered, which shows as an inversed electron demand [4+2] cycloaddition. A new [4+2] adduct on the [5,6]- junction of C70 is isolated as a major product for the first time.Next, an isocyanide-induced multicomponent reaction involving sp-hybridized alkynes or allenes on Lu3N@C80 and C60 will be introduced. The different reactivity and substrate scope of the reactions between fullerenes and metallofullerenes are explored. Notably, one metallofulleroid shows restricted cluster motion caused by the close interaction with the exohedral organic appendant of a neighbor molecule. Finally, further studies in bisaddition reactions on metallofullerenes by utilizing this reaction will be presented.

New functionalization reactions on fullerenes and metallofullerenes

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ACS Fall 2022

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