Issue 19, 2022

A sequential cyclization/π-extension strategy for modular construction of nanographenes enabled by stannole cycloadditions

Abstract

The synthesis of polycyclic aromatic hydrocarbons (PAHs) and related nanographenes requires the selective and efficient fusion of multiple aromatic rings. For this purpose, the Diels–Alder cycloaddition has proven especially useful; however, this approach currently faces significant limitations, including the lack of versatile strategies to access annulated dienes, the instability of the most commonly used dienes, and difficulties with aromatization of the [4 + 2] adduct. In this report we address these limitations via the marriage of two powerful cycloaddition strategies. First, a formal Cp2Zr-mediated [2 + 2 + 1] cycloaddition is used to generate a stannole-annulated PAH. Secondly, the stannoles are employed as diene components in a [4 + 2] cycloaddition/aromatization cascade with an aryne, enabling π-extension to afford a larger PAH. This discovery of stannoles as highly reactive – yet stable for handling – diene equivalents, and the development of a modular strategy for their synthesis, should significantly extend the structural scope of PAHs accessible by a [4 + 2] cycloaddition approach.

Graphical abstract: A sequential cyclization/π-extension strategy for modular construction of nanographenes enabled by stannole cycloadditions

Supplementary files

Article information

Article type
Edge Article
Submitted
21 1 2022
Accepted
29 3 2022
First published
01 4 2022
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2022,13, 5568-5573

A sequential cyclization/π-extension strategy for modular construction of nanographenes enabled by stannole cycloadditions

H. M. Bergman, D. D. Beattie, G. R. Kiel, R. C. Handford, Y. Liu and T. D. Tilley, Chem. Sci., 2022, 13, 5568 DOI: 10.1039/D2SC00397J

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