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Issue 17, 2017
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Integration of oxidative arylation with sulfonyl migration: one-pot tandem synthesis of densely functionalized (NH)-pyrroles

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Abstract

A one-pot synthesis of 2-aryl-3-alkyl/aryl-sulfonyl-(NH)-pyrroles from N-sulfonylpyrroles, developed for the first time, via palladium-catalyzed oxidative C-2 arylation followed by sulfonyl migration is described. The simple, easy access to the highly functionalized free-NH pyrroles secures opportunities for the preparation of compounds with promising biological activities in contemporary organic synthesis. The event of sulfonyl migration from pyrrole-N to C-3 is thermodynamically favored as revealed by density functional methods. The different plausible mechanisms for the migration of the sulfonyl group are also discussed.

Graphical abstract: Integration of oxidative arylation with sulfonyl migration: one-pot tandem synthesis of densely functionalized (NH)-pyrroles

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Publication details

The article was received on 17 May 2017, accepted on 11 Jul 2017 and first published on 12 Jul 2017


Article type: Paper
DOI: 10.1039/C7NJ01709J
Citation: New J. Chem., 2017,41, 8791-8803
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    Integration of oxidative arylation with sulfonyl migration: one-pot tandem synthesis of densely functionalized (NH)-pyrroles

    J. K. Laha, S. Sharma, R. A. Bhimpuria, N. Dayal, G. Dubey and P. V. Bharatam, New J. Chem., 2017, 41, 8791
    DOI: 10.1039/C7NJ01709J

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