Synthesis of polycyclic aromatic hydrocarbons by palladium-catalysed [3 + 3] annulation

Bartłomiej Pigulski; Marta Ximenis; Kazutaka Shoyama; Frank Würthner

doi:10.1039/D0QO00968G

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Synthesis of polycyclic aromatic hydrocarbons by palladium-catalysed [3 + 3] annulation†

Bartłomiej Pigulski,

^a Marta Ximenis,

^a Kazutaka Shoyama

^ab and Frank Würthner

*^ab

Author affiliations

* Corresponding authors

^a Institut für Organische Chemie, Universität Würzburg, Am Hubland, 97074 Würzburg, Germany
E-mail: wuerthner@uni-wuerzburg.de

^b Center for Nanosystems Chemistry (CNC), Universität Würzburg, Theodor-Boveri-Weg, 97074 Würzburg, Germany

Abstract

Here we report a new palladium-catalysed [3 + 3] annulation method for the synthesis of polycyclic aromatic hydrocarbons (PAHs) from two smaller aromatic fragments. The successful application to various perylene derivatives is demonstrated based on optimized reaction conditions for the cross-coupling of 1,8-dibromonaphthalene and 4,5-dibromoacenaphthene with various PAH boronic esters. The reported synthetic protocols could be applied for curved and heteroaromatic substrates as well. The structure and packing arrangements of four products were confirmed by single crystal X-ray diffraction.

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DOI: https://doi.org/10.1039/D0QO00968G
Article type: Research Article
Submitted: 11 Aug 2020
Accepted: 28 Aug 2020
First published: 28 Aug 2020

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Org. Chem. Front., 2020,7, 2925-2930

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Synthesis of polycyclic aromatic hydrocarbons by palladium-catalysed [3 + 3] annulation

B. Pigulski, M. Ximenis, K. Shoyama and F. Würthner, Org. Chem. Front., 2020, 7, 2925 DOI: 10.1039/D0QO00968G

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Organic Chemistry Frontiers

Synthesis of polycyclic aromatic hydrocarbons by palladium-catalysed [3 + 3] annulation†

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Synthesis of polycyclic aromatic hydrocarbons by palladium-catalysed [3 + 3] annulation

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