Acenaphthenoannulation Induced by the Dual Lewis Acidity of Alumina. Issue 31 (26th April 2022)

• Record Type: Journal Article
• Authors: Akhmetov, Vladimir; Feofanov, Mikhail; Ruppenstein, Cordula; Lange, Josefine; Sharapa, Dmitry; Krstić, Marjan; Hampel, Frank; Kataev, Evgeny A.; Amsharov, Konstantin
• Is Part Of: Chemistry. Volume 28:Issue 31(2022)
• Page Start: n/a
• Page End: n/a
• Publication Date: 2022-04-26
• Subjects: alkyne activation -- alumina -- buckybowls -- C−F activation -- geodesic nanoribbons; Chemistry -- Periodicals; 540
• DOI: 10.1002/chem.202200584
• Languages: English
• ISSNs: 0947-6539

Abstract

Abstract: We have discovered a dual (i. e., soft and hard) Lewis acidity of alumina that enables rapid one‐pot π‐extension through the activation of terminal alkynes followed by C−F activation. The tandem reaction introduces an acenaphthene fragment – an essential moiety of geodesic polyarenes. This reaction provides quick access to elusive non‐alternant polyarenes such as π‐extended buckybowls and helicenes through three‐point annulation of the 1‐(2‐ethynyl‐6‐fluorophenyl)naphthalene moiety. The versatility of the developed method was demonstrated by the synthesis of unprecedented structural fragments of elusive geodesic graphene nanoribbons. Abstract : The dual Lewis acidity of γ‐alumina is reported to enable rapid π‐extension of readily available building blocks through the tandem activation of "soft" triple C−C bonds and hard C−F bonds. The reaction gives facile access to elusive non‐alternant polycyclic aromatic hydrocarbons such as π‐extended helicenes and geodesic carbon nanoribbon fragments.