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N-Heterocyclic Carbene-Catalyzed Umpolung of Cyclopent-4-ene-1,3-diones for Activated Olefin–Isatin Cross-Coupling
Organic Letters ( IF 5.2 ) Pub Date : 2022-08-05 , DOI: 10.1021/acs.orglett.2c02413
Shilpa Barik 1 , Sayan Shee 1 , Akkattu T Biju 1
Affiliation  

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.

中文翻译:

N-杂环卡宾催化 Cyclopent-4-ene-1,3-diones 活化烯烃-靛红交叉偶联

介绍了 N-杂环卡宾 (NHC) 催化的 cyclopent-4-ene-1,3-diones 的 umpolung,其通过产生亲核脱氧-Breslow 中间体进行。由市售噻唑鎓盐生成的卡宾催化 cyclopent-4-ene-1,3-diones 和靛红之间的交叉偶联,以中等至良好的产率提供官能化的羟吲哚,并具有良好的官能团相容性。通过 X 射线分析分离和表征了关键的脱氧-Breslow 中间体。还介绍了详细的机理研究。
更新日期:2022-08-05
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