Revisiting hexakis(azulen-2-yl)benzenes: A new synthetic approach using Suzuki cross-coupling

27 March 2025, Version 1
This content is a preprint and has not undergone peer review at the time of posting.

Abstract

Here, we present a novel and significantly shorter synthetic approach to hexakis(azulen-2-yl)benzenes, compared to previously reported strategies. A six-fold Suzuki cross-coupling reaction between hexabromobenzene and borylated azulenes afforded the propeller-shaped hexakis(azulen-2-yl)benzenes 1c and 1d in yields ranging from 46% to 81%. The resulting azulene-containing hydrocarbons were fully characterized, including X-ray single-crystal diffraction analysis. We believe, that these hexakis(azulen-2-yl)benzenes hold great potential as building blocks for larger, conjugated polycyclic aromatic hydrocarbons.

Keywords

azulene
Suzuki reaction
PAH
non-alternant hydrocarbons

Supplementary materials

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Supporting Information
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Copies of NMR, UV/Vis and HRMS spectra
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Supplementary weblinks

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