Electrochemical dehydrogenative α-vinylation and α-allylation of cyclic β-ketoesters

Electrochemical dehydrogenative α-vinylation of cyclic β-ketoesters using 1,1-disubstituted alkenes is reported, producing a diverse range of α-vinyl cycloketones in good yields under oxidant-free conditions. When allylsilanes are used as alkene components, the reaction proceeds through a dual dehydrogenative and desilylative pathway, resulting in the formation of α-allyl cycloketones with good efficiency. This electrochemical strategy provides a unified approach for constructing all-carbon quaternary centers <i>via</i> two distinct α-functionalization processes.

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Publication Details

Journal
Chemical Communications
Published
2025-01-01
DOI
https://doi.org/10.1039/d5cc03082j
Primary Topic
Fluorine in Organic Chemistry
Type
article
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article

Electrochemical dehydrogenative α-vinylation and α-allylation of cyclic β-ketoesters

Ying-Pin Liu, Man‐Su Tu, Junyu Zhai, Jian‐Sheng Sun et al.
Chemical Communications
Fluorine in Organic Chemistry
article

Electrochemical dehydrogenative α-vinylation and α-allylation of cyclic β-ketoesters

Ying-Pin Liu, Man‐Su Tu, Junyu Zhai, Jian‐Sheng Sun, Hao Wu, Bo Jiang, Hao Wen
article en

Abstract

Electrochemical dehydrogenative α-vinylation of cyclic β-ketoesters using 1,1-disubstituted alkenes is reported, producing a diverse range of α-vinyl cycloketones in good yields under oxidant-free conditions. When allylsilanes are used as alkene components, the reaction proceeds through a dual dehydrogenative and desilylative pathway, resulting in the formation of α-allyl cycloketones with good efficiency. This electrochemical strategy provides a unified approach for constructing all-carbon quaternary centers <i>via</i> two distinct α-functionalization processes.

Chemical CommunicationsVol. 61(78)
Jiangsu Normal University (CN)
Openalex Percentile: Top 82%
Fluorine in Organic Chemistry
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