Construction of Acenaphtho[1,2- b ]quinolines through Cyclization of 8-Alkynyl-1-naphthonitriles with Diaryliodonium Salts

Abstract Diaryliodonium salts are known to promote the electrophilic activation of nitriles, typically through copper-catalyzed processes. Herein, we report a metal-free approach to acenaphtho[1,2-b]quinolines through nitrile activation with diaryliodonium salts, followed by an intramolecular [2 + 2 + 2] cyclization. The method enables the introduction of a broad range of substituents onto the aromatic scaffold. The fluorescence properties of the resulting compounds were also investigated, revealing a correlation between the substitution pattern and the emission wavelength.

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Publication Details

Journal
Organic Letters
Published
2026-10-29
DOI
https://doi.org/10.1021/acs.orglett.6c04291
Primary Topic
Oxidative Organic Chemistry Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Construction of Acenaphtho[1,2- b ]quinolines through Cyclization of 8-Alkynyl-1-naphthonitriles with Diaryliodonium Salts

Sébastien Prévost, G. Zucchi, Nicolas Casaretto, Eugénie Roullier et al.
Organic Letters
Oxidative Organic Chemistry Reactions
article

Construction of Acenaphtho[1,2- b ]quinolines through Cyclization of 8-Alkynyl-1-naphthonitriles with Diaryliodonium Salts

Sébastien Prévost, G. Zucchi, Nicolas Casaretto, Eugénie Roullier, Shanshan Liu, Enzo Bequet
article en

Abstract

Abstract Diaryliodonium salts are known to promote the electrophilic activation of nitriles, typically through copper-catalyzed processes. Herein, we report a metal-free approach to acenaphtho[1,2-b]quinolines through nitrile activation with diaryliodonium salts, followed by an intramolecular [2 + 2 + 2] cyclization. The method enables the introduction of a broad range of substituents onto the aromatic scaffold. The fluorescence properties of the resulting compounds were also investigated, revealing a correlation between the substitution pattern and the emission wavelength.

Organic Letters
Centre National de la Recherche Scientifique (FR), École Polytechnique (FR), École Nationale Supérieure de Techniques Avancées (FR), Institut Polytechnique de Paris (FR)
Institut Polytechnique de Paris, China Scholarship Council, Centre National de la Recherche Scientifique
Openalex Percentile: Top 26%
Oxidative Organic Chemistry Reactions
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