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

Venkatachalam Rajeshkumar, Fu‐Wei Chan, Shih‐Ching Chuang

Advanced Synthesis & Catalysis · 2012 · 37 citations · 85 references

Concepts

Abstract

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 C 60 ).

References

85