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Six-fold C–H Borylation of Hexa-peri-hexabenzocoronene

Mai Nagase, Kenta Kato, Akiko Yagi, Yasutomo Segawa,* and Kenichiro Itami*
Beilstein J. Org. Chem. 2020, 16, 391-397. DOI: 10.3762/bjoc.16.37

Hexa-peri-hexabenzocoronene (HBC) is known to be a poorly soluble polycyclic aromatic hydrocarbon for which direct functionalization methods have been very limited. Herein, the synthesis of hexaborylated HBC from unsubstituted HBC is described. Iridium-catalyzed six-fold C–H borylation of HBC was successfully achieved by screening solvents. The crystal structure of hexaborylated HBC was confirmed via X-ray crystallography. Optoelectronic properties of the thus-obtained hexaborylated HBC were analyzed with the support of density functional theory calculations. The spectra revealed a bathochromic shift of absorption bands compared with unsubstituted HBC under the effect of the σ-donation of boryl groups.

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