Journal
CHEMISTRY-A EUROPEAN JOURNAL
Volume 24, Issue 53, Pages 14075-14078Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/chem.201803676
Keywords
azacorannulenes; buckybowls; C-H borylation; cross-coupling; liquid crystals
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Funding
- Japan Society for the Promotion of Science (JSPS) KAKENHI, Japan [16H06030]
- MEXT, Japan
- JSPS
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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 -conjugated cores.
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