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
21 ذو الحجة 1441
Accepted
09 محرم 1442
First published
09 محرم 1442

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

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements