Palladium-Catalyzed Cyclization: Regioselectivity and Structure of Arene-Fused C_(60) Derivatives

摘要

The palladium-catalyzed cyclization on the fullerene C_(60) cage has been achieved using several aryl halides and C_(60). This reaction was found to be accelerated by the addition of pivalic acid, which can be rationally explained by the computational study based on the concerted metalation-deprotonation mechanism. We also demonstrated the regioselective π-functionalization using prefunctionalized designed molecules possessing the same substructure on the C_(60) cage. The single crystal X-ray analysis and electrostatic potential map revealed that the orientation of entrapped H_2O inside the naphthalene-fused open-cage C_(60) derivative is electrostatically demanded due to the naphthalene-fusion and construction of the opening.