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

Laha, Joydev K. ; Sharma, Shubhra ; Bhimpuria, Rohan A. ; Dayal, Neetu ; Dubey, Gurudutt ; Bharatam, Prasad V. (2017) Integration of oxidative arylation with sulfonyl migration: one-pot tandem synthesis of densely functionalized (NH)-pyrroles New Journal of Chemistry, 41 (17). pp. 8791-8803. ISSN 1144-0546

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Official URL: http://doi.org/10.1039/C7NJ01709J

Related URL: http://dx.doi.org/10.1039/C7NJ01709J

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.

Item Type:Article
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ID Code:116328
Deposited On:12 Apr 2021 09:24
Last Modified:12 Apr 2021 09:24

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