Synthesis of Polybenzoacenes: Annulative Dimerization of Phenylene Triflate by Twofold C−H Activation
Correction(s) for this article
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Berichtigung: Synthesis of Polybenzoacenes: Annulative Dimerization of Phenylene Triflate by Twofold C−H Activation
- Volume 133Issue 11Angewandte Chemie
- pages: 5659-5659
- First Published online: March 1, 2021
Mizuho Uryu
Graduate School of Science, Nagoya University, Chikusa, Nagoya, 464-8602 Japan
These authors contributed equally to this work.
Search for more papers by this authorTaito Hiraga
Graduate School of Science, Nagoya University, Chikusa, Nagoya, 464-8602 Japan
These authors contributed equally to this work.
Search for more papers by this authorYoshito Koga
Graduate School of Science, Nagoya University, Chikusa, Nagoya, 464-8602 Japan
Search for more papers by this authorDr. Yutaro Saito
Graduate School of Science, Nagoya University, Chikusa, Nagoya, 464-8602 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Kei Murakami
Graduate School of Science, Nagoya University, Chikusa, Nagoya, 464-8602 Japan
Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya, 464-8602 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Kenichiro Itami
Graduate School of Science, Nagoya University, Chikusa, Nagoya, 464-8602 Japan
Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya, 464-8602 Japan
JST-ERATO, Itami Molecular Nanocarbon Project, Nagoya University, Chikusa, Nagoya, 464-8602 Japan
Search for more papers by this authorMizuho Uryu
Graduate School of Science, Nagoya University, Chikusa, Nagoya, 464-8602 Japan
These authors contributed equally to this work.
Search for more papers by this authorTaito Hiraga
Graduate School of Science, Nagoya University, Chikusa, Nagoya, 464-8602 Japan
These authors contributed equally to this work.
Search for more papers by this authorYoshito Koga
Graduate School of Science, Nagoya University, Chikusa, Nagoya, 464-8602 Japan
Search for more papers by this authorDr. Yutaro Saito
Graduate School of Science, Nagoya University, Chikusa, Nagoya, 464-8602 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Kei Murakami
Graduate School of Science, Nagoya University, Chikusa, Nagoya, 464-8602 Japan
Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya, 464-8602 Japan
Search for more papers by this authorCorresponding Author
Prof. Dr. Kenichiro Itami
Graduate School of Science, Nagoya University, Chikusa, Nagoya, 464-8602 Japan
Institute of Transformative Bio-Molecules (WPI-ITbM), Nagoya University, Chikusa, Nagoya, 464-8602 Japan
JST-ERATO, Itami Molecular Nanocarbon Project, Nagoya University, Chikusa, Nagoya, 464-8602 Japan
Search for more papers by this authorAbstract
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.
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