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Dibenzopleiadiene-embeded polyaromatics via [4 + 3] annulative decarbonylation/decarboxylation

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Abstract

A novel strategy is developed for the synthesis of dibenzopleiadiene-embedded polycyclic aromatic hydrocarbons from 1,8-naphthalic anhydride derivatives and cyclic diaryliodonium salts through a palladium-catalyzed cascade [4 + 3] decarbonylative/decarboxylative annulation. The mechanism of the reaction is proposed and the molecular structure, photophysical properties, and frontier molecular orbitals of diverse dibenzopleiadiene-embedded polyaromatics are elucidated by X-ray crystallography, UV-Vis and fluorescence spectroscopy, and DFT calculations.

Graphical abstract: Dibenzopleiadiene-embeded polyaromatics via [4 + 3] annulative decarbonylation/decarboxylation

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Article information


Submitted
06 Aug 2020
Accepted
16 Sep 2020
First published
18 Sep 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

Dibenzopleiadiene-embeded polyaromatics via [4 + 3] annulative decarbonylation/decarboxylation

K. Kantarod, T. Worakul, D. Soorukram, C. Kuhakarn, V. Reutrakul, P. Surawatanawong, W. Wattanathana and P. Leowanawat, Org. Chem. Front., 2020, Advance Article , DOI: 10.1039/D0QO00942C

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