Integration of oxidative arylation with sulfonyl migration: one-pot tandem synthesis of densely functionalized (NH)-pyrrolesElectronic supplementary information (ESI) available. CCDC 1544189. For ESI and crystallographic data in CIF or other electronic format see DOI: 10.1039/c7nj01709j

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 opportu...

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Main Authors: Laha, Joydev K, Sharma, Shubhra, Bhimpuria, Rohan A, Dayal, Neetu, Dubey, Gurudutt, Bharatam, Prasad V
Format: Article
Language:English
Online Access:Get full text
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Summary: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. 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.
ISSN:1144-0546
1369-9261
DOI:10.1039/c7nj01709j