Synthesis of Oxygen-Substituted Hexa-<i>peri</i>-hexabenzocoronenes through Ir-Catalyzed Direct Borylation

Direct C–H borylation of hexa-peri-hexabenzocoronenes (HBCs) has been achieved under iridium catalysis, which allows efficient synthesis of hydroxy-substituted HBCs by oxidation of the boryl groups. Further oxidation of dihydroxy HBC with phenyliodine bis(trifluoroacetate) (PIFA) afforded tetraoxo-substituted HBC without any regioisomers, which can be considered as a π-extended quinone.