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Issue 11, 2017
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Post-synthetic diversification of pyrrole-fused benzosultams via trans-sulfonylations and reactions on the periphery of pyrrole

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Abstract

The chemistry (synthesis and reactions) of pyrrole-fused benzosultams has been the subject of this current investigation. Their workable access via palladium-catalyzed oxidative coupling has made this study feasible. The trans-sulfonylation in pyrrole-fused benzosultams provided access to otherwise unattainable (NH)-2-arylpyrroles containing an ortho-sulfonamide functionality. Other N–SO2 bond cleavages in pyrrole-fused benzosultams yielded synthetically useful (NH)-2-arylpyrroles containing other ortho-sulfonyl functionality. A terminal amine or hydroxyl functionality, ideally poised for bioconjugation, is another important feature of some of the synthesized (NH)-2-arylpyrroles. The rationally designed and synthesised novel fluorenes tethered with pyrrole-fused benzosultam could find applications as organic emitters in organic light-emitting devices (OLEDs).

Graphical abstract: Post-synthetic diversification of pyrrole-fused benzosultams via trans-sulfonylations and reactions on the periphery of pyrrole

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Publication details

The article was received on 02 Jun 2017, accepted on 27 Jul 2017 and first published on 28 Jul 2017


Article type: Research Article
DOI: 10.1039/C7QO00440K
Citation: Org. Chem. Front., 2017,4, 2170-2174
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    Post-synthetic diversification of pyrrole-fused benzosultams via trans-sulfonylations and reactions on the periphery of pyrrole

    J. K. Laha, R. A. Bhimpuria and A. M. Kumar, Org. Chem. Front., 2017, 4, 2170
    DOI: 10.1039/C7QO00440K

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