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Azaindenocorannulenes: Synthesis, Properties, and Chirality

By Xiaoqi Tian, Loïc Roch, Nicolas Vanthuyne, Jun Xu, Kim Baldridge and Jay Siegel


International audiencePalladium-catalyzed intramolecular arylation provides bowl-shaped azaindenocorannulenes 7−9. Crystals of 8 show bowl-in-bowl columnar stacking. A substituent model rationalizes the first reduction potential of 18 related molecular bowls. The absolute configurations of bowls 7 and 9 are correlated with VCD and ECD spectra. The bowl inversion barrier of 9 (>190 kJ/mol) shows it to be more inert configurationally than chiral biaryl, phosphenes, or [n]helicenes

Topics: [CHIM.ORGA]Chemical Sciences/Organic chemistry, [CHIM.CATA]Chemical Sciences/Catalysis
Publisher: 'American Chemical Society (ACS)'
Year: 2019
DOI identifier: 10.1021/acs.orglett.9b00718
OAI identifier: oai:HAL:hal-02514517v1
Provided by: HAL AMU
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