Visible-Light Photoredox-Catalyzed Alkylation/1,2-Aryl Migration of Allylic Alcohols with Malonic Esters Leading to δ-Keto Esters

A visible-light photoredox-catalyzed strategy has been developed for the synthesis of δ-keto esters through alkylation/1,2-aryl migration of allylic alcohols with malonic esters. This transformation could be undergone at room temperature in a step- and atom-economic manner by using Eosin Y and air as a metal-free photocatalyst and green oxidant, respectively. Preliminary mechanistic analysis suggested that 1,2-aryl migration proceeded through a radical process.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-12-23
DOI
https://doi.org/10.1021/acs.joc.5c02904
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Visible-Light Photoredox-Catalyzed Alkylation/1,2-Aryl Migration of Allylic Alcohols with Malonic Esters Leading to δ-Keto Esters

Wei Wu, Yimou Gong, Dong Yi, Zuli Wang et al.
The Journal of Organic Chemistry
Radical Photochemical Reactions
article

Visible-Light Photoredox-Catalyzed Alkylation/1,2-Aryl Migration of Allylic Alcohols with Malonic Esters Leading to δ-Keto Esters

Wei Wu, Yimou Gong, Dong Yi, Zuli Wang, Zi Yang, Huilan Yue, Zhuoming Ma, Huanhuan Cui
article en

Abstract

A visible-light photoredox-catalyzed strategy has been developed for the synthesis of δ-keto esters through alkylation/1,2-aryl migration of allylic alcohols with malonic esters. This transformation could be undergone at room temperature in a step- and atom-economic manner by using Eosin Y and air as a metal-free photocatalyst and green oxidant, respectively. Preliminary mechanistic analysis suggested that 1,2-aryl migration proceeded through a radical process.

The Journal of Organic ChemistryVol. 91(1)
Changsha Medical University (CN), Nanjing Forestry University (CN), Southwest Medical University (CN), Qinghai Tibetan Hospital (CN), Green Chemistry (PL), Zaozhuang University (CN), Northwest Institute of Plateau Biology
Openalex Percentile: Top 33%
Radical Photochemical Reactions
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Visible-Light Photoredox-Catalyzed Alkylation/1,2-Aryl Migration of Allylic Alcohols with Malonic Esters Leading to δ-Keto Esters — Wei Wu, Yimou Gong, et al. · The Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS