Synthesis of Polybenzoacenes: Annulative Dimerization of Phenylene Triflate by Twofold C–H Activation

“Synthesis of Polybenzoacenes: Annulative Dimerization of Phenylene Triflate by Twofold C–H Activation”
Mizuho Uryu,† Taito Hiraga,† Yoshito Koga, Yutaro Saito, Kei Murakami,* Kenichiro Itami*
Angew. Chem., Int. Ed. 2020, Early View. DOI: 10.1002/anie.202001211.



Polycyclic aromatic hydrocarbons (PAHs) have attracted a broad interest for organic electronic devices, including field effect transistors and photovoltaics. Because their properties depend on structures, the development of a straightforward and efficient approach to PAHs is still in high demand.

Herein we have developed an annulative dimerization of phenylene triflate through double C–H activation. This reaction showed a broad scope of phenylene triflate. In particular, dimerization proceeded regioselectively when a phenyl triflate with pyrene structure is used. One of the major advantages of this methodology is that dibenzofuran derivatives can be used as precursors for 2-hydroxybiphenyl. Thereafter, fully fused PAHs can be derived from the dimerizatio products through Scholl reaction. This study presented a new strategy for PAH synthesis using phenol derivatives and dibenzofuran derivatives as feedstocks.

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