Palladium-Catalyzed and Hybrid Acids-Assisted Synthesis of [60]Fulleroazepines in One Pot under Mild Conditions: Annulation of N-Sulfonyl-2-aminobiaryls with [60]Fullerene through Sequential C-H Bond Activation, C-C and C-N Bond Formation

Abstract

An extraordinarily efficient hybrid acids-assisted, palladium-catalyzed and chelating-group-assisted C?H bond activation of N-sulfonyl-2-aminobiaryls and their annulations with [60]fullerene via sequential C?C and C?N bond formation at room temperature to afford [60]fulleroazepines is demonstrated. The formation of [60]fulleroazepines is highly regioselective and tolerant to both electron-withdrawing and electron-donating groups on the aryl moiety and the reaction gives monofunctionalized fullerenes in good yields (up to 54% isolated yield and 92% based on converted C60).