Dramatic Mechanistic Change in Acid-Catalyzed Arylation of Azafulleroids Depending on their Ambident N/C Basicity: Formation of Cyclopentene Centered Pentakisadduct

作者：Ikuma Naohiko^*; Doi Yuta; Fujioka Koichi; Mikie Tsubasa; Kokubo Ken; Oshima Takumi

来源：Chemistry-An Asian Journal, 2014, 9(11): 3084-3088.

DOI：10.1002/asia.201402728

• arylation
• homogeneous catalysis
• fullerenes
• nucleophilic substitution
• protonation

Azafulleroid, amino-bridged [5,6]-open fullerene, has the ambident N/C basicity of the incorporated enamine moiety. Acid-catalyzed arylation of N-substituted azafulleroids proceeded via two types of initial N/C protonation to perform monoarylation or 1,4-bisarylation for the N-alkyl substituents and shuttlecock-type pentakisarylation for the N-phenyl substituent. The dramatic product change was explained by considering the possible mechanism as well as the DFT computational results.

• 出版日期2014-11