ol9b00718_si_001.pdf (4.4 MB)
Azaindenocorannulenes: Synthesis, Properties, and Chirality
journal contribution
posted on 2019-04-17, 17:03 authored by Xiaoqi Tian, Loïc M. Roch, Nicolas Vanthuyne, Jun Xu, Kim K. Baldridge, Jay S. SiegelPalladium-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.