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Lipophilic indole mediated chemoselective α-monobromination of 1,3-dicarbonyl compounds
Tetrahedron Letters ( IF 1.5 ) Pub Date : 2020-02-22 , DOI: 10.1016/j.tetlet.2020.151772
Jonathan Wong , Zhihai Ke , Ying-Yeung Yeung

A mild and efficient mono-selective bromination of 1,3-dicarbonyl compounds has been developed using lipophilic indole catalysts. Inexpensive and commercially available N-bromosuccinimide (NBS) was used as the brominating reagent. The selectivity was further enhanced when using stoichiometric amount of 3-bromoindole species. Mechanistic studies reveal that the indole catalyst has dual functions in the mono-bromination process.



中文翻译:

亲脂吲哚介导的1,3-二羰基化合物的化学选择性α-单溴化

已经使用亲脂性吲哚催化剂开发了温和而有效的1,3-二羰基化合物的单选择溴化反应。廉价且可商购的N-溴琥珀酰亚胺(NBS)用作溴化试剂。当使用化学计量的3-溴吲哚类时,选择性进一步提高。机理研究表明,吲哚催化剂在单溴化过程中具有双重功能。

更新日期:2020-02-23
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