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Issue 11, 2016
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A cross-coupling-annulation cascade from peri-dibromonaphthalimide to pseudo-rylene bisimides

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Abstract

Herein we report a synthetic method to annulate naphthalimide moieties at different positions of a pyrene core by a cascade reaction involving palladium-mediated Suzuki–Miyaura cross-coupling and direct C–H arylation affording a new class of rylene bisimides, which we term as pseudo-rylene bisimides. The Pd-mediated reactions of peri-dibromonaphthalimide and pyrene boronic acid esters lead exclusively to six-membered ring annulation by a cascade C–C bond formation, for which a mechanistic rationale is proposed. Depending on the molecular geometry of the new pseudo-rylene bisimides, their optical properties resemble those of zethrene or terrylene bisimides, or polycyclic aromatic hydrocarbons like coronenes. The structural integrity of this new type of pseudo-rylene bisimides was confirmed by single crystal X-ray analysis.

Graphical abstract: A cross-coupling-annulation cascade from peri-dibromonaphthalimide to pseudo-rylene bisimides

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Publication details

The article was received on 01 Aug 2016, accepted on 06 Sep 2016 and first published on 14 Sep 2016


Article type: Research Article
DOI: 10.1039/C6QO00421K
Citation: Org. Chem. Front., 2016,3, 1435-1442
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    A cross-coupling-annulation cascade from peri-dibromonaphthalimide to pseudo-rylene bisimides

    S. Seifert, D. Schmidt and F. Würthner, Org. Chem. Front., 2016, 3, 1435
    DOI: 10.1039/C6QO00421K

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