Oxidative rearrangement of indoles mediated by 2-bromoethanol and hydrogen peroxide to access spirooxindoles

Oxidative rearrangement of indoles into a series of spirooxindoles has been accomplished by using an exclusive reagent system containing 2-bromoethanol and hydrogen peroxide. This alternative metal-free approach features utilization of HOBr, generated <i>in situ</i> from the reaction of 2-bromoethanol and hydrogen peroxide <i>via</i> a radical pathway, as an electrophilic species to enable the spirolization to occur.

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Publication Details

Journal
Organic & Biomolecular Chemistry
Published
2025-01-01
DOI
https://doi.org/10.1039/d5ob01126d
Primary Topic
Oxidative Organic Chemistry Reactions
Type
article
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article

Oxidative rearrangement of indoles mediated by 2-bromoethanol and hydrogen peroxide to access spirooxindoles

Dongxue Yin, Haofeng Shi, Dan Xiao, Kaiyue Yang et al.
Organic & Biomolecular Chemistry
Oxidative Organic Chemistry Reactions
article

Oxidative rearrangement of indoles mediated by 2-bromoethanol and hydrogen peroxide to access spirooxindoles

Dongxue Yin, Haofeng Shi, Dan Xiao, Kaiyue Yang, Zhijian Wang, Jiaxin He, Yunfei Du, Yingjie Gao
article en

Abstract

Oxidative rearrangement of indoles into a series of spirooxindoles has been accomplished by using an exclusive reagent system containing 2-bromoethanol and hydrogen peroxide. This alternative metal-free approach features utilization of HOBr, generated <i>in situ</i> from the reaction of 2-bromoethanol and hydrogen peroxide <i>via</i> a radical pathway, as an electrophilic species to enable the spirolization to occur.

Organic & Biomolecular ChemistryVol. 23(37)
Tianjin University (CN), Tianjin Institute of Pharmaceutical Research (China) (CN)
Openalex Percentile: Top 83%
Oxidative Organic Chemistry Reactions
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