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- Title
Functionalization of Azapentabenzocorannulenes by Fivefold C−H Borylation and Cross‐Coupling Arylation: Application to Columnar Liquid‐Crystalline Materials.
- Authors
Nagano, Taro; Nakamura, Kimihiro; Tokimaru, Yuki; Ito, Shingo; Miyajima, Daigo; Aida, Takuzo; Nozaki, Kyoko
- Abstract
Abstract: 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 assemble into 1D hexagonal columnar structures over a wide temperature range. The present method expands the variety and utility of azapentabenzocorannulenes as promising π‐conjugated cores.
- Subjects
BORYLATION; COUPLING reactions (Chemistry); ARYLATION; LIQUID crystals; IRIDIUM catalysts
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 53, p14075
- ISSN
0947-6539
- Publication type
Article
- DOI
10.1002/chem.201803676