Palladium-Catalyzed Three-Component 1,4-Alkoxyarylation Reaction of [60]Fullerene

Abstract

The palladium-catalyzed three-component alkoxyarylation reaction of [60]­fullerene with primary/secondary alcohols and aryl iodides generates a series of 1,4-(alkoxy)­(aryl)[60]­fullerene derivatives. Plausible reaction pathways for the formation of 1,4-(alkoxy)­(aryl)[60]­fullerenes are proposed. In addition, the electrochemical properties of the synthesized 1,4-alkoxyarylation adducts are investigated.

KOtBu-Promoted, Three-Component Domino Reaction of Arenes(indoles/phenols), C60, and (Per/poly)fluoroarenes: Achieving Direct C–C Cross-Coupling of Fullerene with (Per/poly)fluoroarenes

“…Recently, with the constant efforts of chemists, potassium tert -butoxide (KO t Bu)-promoted cross-coupling has matured into a versatile and efficient tool for constructing the C–C bond . In consideration of the tremendous potential of metal salt-promoted or -catalyzed reactions for the synthesis of novel fullerene derivatives, − we are interested in developing KO t Bu-promoted fullerene functionalization methods . Inspired by our previous work, we focused on the transition-metal-free direct selective C–C coupling of various (per/poly)­fluoroarenes with C 60 .…”

Synthesis of diverse unsymmetric 1,4-adducts via a three-component coupling reaction of malonate derivatives, [60]fullerene and electrophiles/nucleophiles

“…Among the large number of methods for preparing organic group functionalized C 60 derivatives, 1,4-unsymmetric difunctionalization of [60]fullerene(C 60 ) has become one of the important methods to synthesize many useful fullerene material molecules in recent years. 8 b,c ,9 b ,10–12 The two different organic functional groups on the 1,4-position not only completely changed the spheriform symmetry of the C 60 core from I h to C 1 , but also produced a unique broad absorption in the UV-region, increased absorption in the visible light region, and a higher LUMO energy level compared with that of the 1,2-adducts. 1 b , d ,9 b More importantly, physical properties of the 1,4-bisadducts such as solubility, visible light absorption, and LUMO energy level could be tuned by switching different combinations of organic addends on fullerene.…”

Assembly of Diverse [60]Fullerene-Fused Tricyclic Scaffolds via a Palladium-Catalyzed Cascade [2 + 2 + 2] Annulation Reaction

“…Fullerene species have garnered considerable interest in material science, biomedical chemistry, solar energy conversion, and catalysis . Chemical functionalization is a powerful tool to create structurally diverse fullerene species, and a variety of synthetic routes toward functionalization of fullerenes have been established in succession over the past 30 years. , Seeking facile and efficient protocols for the direct construction of complex and intriguing molecular architectures from simple or readily available starting materials in a step-economical process has been the pursuit of synthetic chemists, and this also applies to functionalization of fullerenes. For example, Nakamura and co-workers developed a highly selective multiaddition reaction for the facile construction of penta­(aryl)[60]­fullerenes from organocopper reagents [derived from Grignard reagents and copper­(I) halide] to fullerenes. , Gan et al demonstrated easy access to C 60 (O)­(OO t Bu) 4 and C 70 (OO t Bu) 10 via metal-catalyzed mixed peroxide addition reactions of tert -butyl hydroperoxide with fullerenes .…”