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Synthesis of Polybenzoacenes: Annulative Dimerization of Phenylene Triflate by Twofold C−H Activation
Author(s) -
Uryu Mizuho,
Hiraga Taito,
Koga Yoshito,
Saito Yutaro,
Murakami Kei,
Itami Kenichiro
Publication year - 2020
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202001211
Subject(s) - trifluoromethanesulfonate , chemistry , phenanthrene , conjugated system , intramolecular force , aryl , phenylene , phenol , combinatorial chemistry , molecule , catalysis , organic chemistry , polymer , alkyl
Polycyclic aromatic hydrocarbons (PAHs) represent an emerging class of π‐conjugated molecules in the area of optoelectronic devices and materials. Unprecedented synthetic routes to various PAHs from simple phenol derivatives by a palladium‐catalyzed annulative dimerization of phenylene triflate through twofold inter‐ and intramolecular C−H activation have been established. The initially formed partially fused PAHs can be smoothly transformed into a variety of fully fused PAHs by the Scholl reaction. Furthermore, the reactions of phenanthrene‐substituted aryl triflates proceeded regioselectively. The findings inspired the development of a rapid and efficient synthesis of polybenzoacene derivatives. This study not only allows transformation of phenyl triflates, but also discloses a new retrosynthetic strategy towards PAHs, especially polybenzoacenes.