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Issue 74, 2018
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Metal-free naphthannulation reactions of yne-allenone esters for accessing polycyclic aromatic hydrocarbons

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Abstract

The first metal-free base-promoted naphthannulation reactions of yne-allenone esters were established for the direct assembly of a wide range of polycyclic aromatic hydrocarbons with generally good yields. The naphthannulation reaction of yne-allenone esters with β-ketonitriles provided new phenanthrene-1-carboxylates via a base-mediated [2+2] cycloaddition/ring expansion sequence, whereas hitherto unreported tetracyclic tetrahydrotetraphene-7-carboxylates were obtained with good yield via a sequential double annulation cascade of yne-allenone esters with dimedone as a diphilic reagent.

Graphical abstract: Metal-free naphthannulation reactions of yne-allenone esters for accessing polycyclic aromatic hydrocarbons

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Publication details

The article was received on 23 Jun 2018, accepted on 25 Jul 2018 and first published on 26 Jul 2018


Article type: Communication
DOI: 10.1039/C8CC05018J
Citation: Chem. Commun., 2018,54, 10415-10418
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    Metal-free naphthannulation reactions of yne-allenone esters for accessing polycyclic aromatic hydrocarbons

    H. Sha, T. Xu, F. Liu, B. Tang, W. Hao, S. Tu and B. Jiang, Chem. Commun., 2018, 54, 10415
    DOI: 10.1039/C8CC05018J

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