Acenaphthenoannulation Induced by the Dual Lewis Acidity of Alumina

Overview

Journal Chemistry

Specialty Chemistry

Date 2022 Mar 21

PMID 35313382

Authors

Vladimir Akhmetov

Mikhail Feofanov

Cordula Ruppenstein

Josefine Lange

Dmitry Sharapa

Marjan Krstic

Frank Hampel

Evgeny A Kataev

Konstantin Amsharov

Affiliations

Soon will be listed here.

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.

Citing Articles

Acenaphthenoannulation Induced by the Dual Lewis Acidity of Alumina.

Akhmetov V, Feofanov M, Ruppenstein C, Lange J, Sharapa D, Krstic M Chemistry. 2022; 28(31):e202200584.

PMID: 35313382 PMC: 9321853. DOI: 10.1002/chem.202200584.

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