DOI: 10.1021/acs.orglett.6c04291 ISSN: 1523-7060
Construction of Acenaphtho[1,2- b ]quinolines through Cyclization of 8-Alkynyl-1-naphthonitriles with Diaryliodonium Salts
Shanshan Liu, Enzo Bequet, Eugénie Roullier, Nicolas Casaretto, Gaël Zucchi, Sébastien PrévostAbstract
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.