N-Heterocyclic Carbene-Catalyzed Umpolung of Cyclopent-4-ene-1,3-diones for Activated Olefin-Isatin Cross-Coupling

Barik, S and Shee, S and Biju, AT (2022) N-Heterocyclic Carbene-Catalyzed Umpolung of Cyclopent-4-ene-1,3-diones for Activated Olefin-Isatin Cross-Coupling. In: Organic Letters, 24 (32). pp. 6066-6071.

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Abstract

N-Heterocyclic carbene (NHC)-catalyzed umpolung of cyclopent-4-ene-1,3-diones that proceeds via the generation of nucleophilic deoxy-Breslow intermediates is presented. The carbene generated from a commercially available thiazolium salt catalyzed the cross-coupling between cyclopent-4-ene-1,3-diones and isatins to furnish the functionalized oxindoles in moderate to good yields with good functional group compatibility. The key deoxy-Breslow intermediates were isolated and characterized by X-ray analysis. Detailed mechanistic studies are also presented.

Item Type:	Journal Article
Publication:	Organic Letters
Publisher:	American Chemical Society
Additional Information:	The copyright for this article belongs to the American Chemical Society.
Department/Centre:	Division of Chemical Sciences > Organic Chemistry
Date Deposited:	13 Sep 2022 06:53
Last Modified:	13 Sep 2022 06:53
URI:	https://eprints.iisc.ac.in/id/eprint/76762

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