Issue 11, 2017

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
02 Jun 2017
Accepted
27 Jul 2017
First published
28 Jul 2017

Org. Chem. Front., 2017,4, 2170-2174

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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