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Gold-catalyzed regiospecific C-H annulation of o-ethynylbiaryls with anthranils: π-extension by ring-expansion en route to N-doped PAHs

We describe a novel, short, and flexible approach to diverse N-doped polycyclic aromatic hydrocarbons (PAHs) through gold-catalyzed π-extension of anthranils with o-ethynylbiaryls as reagents. This strategy uses easily accessible starting materials, is simple due to high step and atom economy, and s...

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Bibliographic Details
Main Authors: Zeng, Zhongyi (Author) , Jin, Hongming (Author) , Sekine, Kohei (Author) , Rudolph, Matthias (Author) , Rominger, Frank (Author) , Hashmi, A. Stephen K. (Author)
Format: Article (Journal)
Language:English
Published: 06 April, 2018
In: Angewandte Chemie. International edition
Year: 2018, Volume: 57, Issue: 23, Pages: 6935-6939
ISSN:1521-3773
DOI:10.1002/anie.201802445
Online Access:Verlag, Volltext: http://dx.doi.org/10.1002/anie.201802445
Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201802445
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Author Notes:Zhongyi Zeng, Hongming Jin, Kohei Sekine, Matthias Rudolph, Frank Rominger, A. Stephen K. Hashmi
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Summary:We describe a novel, short, and flexible approach to diverse N-doped polycyclic aromatic hydrocarbons (PAHs) through gold-catalyzed π-extension of anthranils with o-ethynylbiaryls as reagents. This strategy uses easily accessible starting materials, is simple due to high step and atom economy, and shows good functional-group compatibility as well as scale-up potential. Mechanistically, the tandem reaction is proposed to involve a nucleophilic addition/ring opening/regiospecific C−H annulation/protodeauration sequence terminated by a Friedel-Crafts-type cyclization. Photophysical studies of the products indicated violet-blue fluorescence emission with quantum yields up to 0.45.
Item Description:Gesehen am 27.08.2018
Physical Description:Online Resource
ISSN:1521-3773
DOI:10.1002/anie.201802445

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