Issue 19, 2020

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

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.

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

Supplementary files

Article information

Article type
Research Article
Submitted
11 aug 2020
Accepted
28 aug 2020
First published
28 aug 2020

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

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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