Barik, Shilpa ; Shee, Sayan ; Biju, Akkattu T. (2022) N-Heterocyclic Carbene-Catalyzed Umpolung of Cyclopent-4-ene-1,3-diones for Activated Olefin–Isatin Cross-Coupling Organic Letters, 24 (32). pp. 6066-6071. ISSN 1523-7060
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Official URL: http://doi.org/10.1021/acs.orglett.2c02413
Related URL: http://dx.doi.org/10.1021/acs.orglett.2c02413
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: | Article |
|---|---|
| Source: | Copyright of this article belongs to American Chemical Society |
| ID Code: | 128574 |
| Deposited On: | 03 Nov 2022 05:59 |
| Last Modified: | 03 Nov 2022 05:59 |
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