Functionalization of Azapentabenzocorannulenes by Fivefold C-H Borylation and Cross-Coupling Arylation: Application to Columnar Liquid-Crystalline Materials.

  title={Functionalization of Azapentabenzocorannulenes by Fivefold C-H Borylation and Cross-Coupling Arylation: Application to Columnar Liquid-Crystalline Materials.},
  author={Taro Nagano and Kimihiro Nakamura and Yuki Tokimaru and Shingo Ito and Daigo Miyajima and Takuzo Aida and Kyoko Nozaki},
  volume={24 53},
Herein, the one-shot fivefold functionalization of azapentabenzocorannulenes by an iridium-catalyzed fivefold C-H borylation reaction that exhibits excellent regioselectivity is reported. The borylated product can be used as a versatile synthetic intermediate for further derivatization via Suzuki-Miyaura cross-coupling reactions. This fivefold borylation/arylation sequence was employed to synthesize liquid-crystalline azapentabenzocorannulenes with five 3,4,5-trialkoxyphenyl groups, which… 
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