Intramolecular Aryl–Aryl Coupling of Fluoroarenes through Al2O3-Mediated HF Elimination

A strategy for effective intramolecular aryl–aryl coupling of fluoroarenes through Al2O3-mediated HF elimination is reported. It is demonstrated that the C–F bond, which is widely believed to be the most passive functionality in organic chemistry, can be reconsidered as a useful functional group all...

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Veröffentlicht in:Journal of organic chemistry 2012-06, Vol.77 (12), p.5445-5448
Hauptverfasser: Amsharov, K.Yu, Merz, P
Format: Artikel
Sprache:eng
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Zusammenfassung:A strategy for effective intramolecular aryl–aryl coupling of fluoroarenes through Al2O3-mediated HF elimination is reported. It is demonstrated that the C–F bond, which is widely believed to be the most passive functionality in organic chemistry, can be reconsidered as a useful functional group allowing very effective C–C bond formation. The solid-state strategy presented in this study opens the possibility for facile syntheses of insoluble extended polycyclic aromatic hydrocarbons.
ISSN:0022-3263
1520-6904
DOI:10.1021/jo300783y