Catalytic Aldehyde–Alkyne Couplings Triggered by Ketyl Radicals

A general and flexible platform for catalytic aldehyde-alkyne couplings triggered by ketyl radicals is described. This open-shell strategy necessitates only a catalytic quantity of a photoredox catalyst, along with Hünig's base (DIPEA) as a halogen atom transfer reagent. The reaction proceeds through sequential steps involving activation, halogen atom transfer, and radical addition. This carbonyl-alkyne coupling exhibits a wide substrate scope and functional group compatibility and has been successfully applied to the late-stage modification of complex architectures.

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Publication Details

Journal
Organic Letters
Published
2024-11-08
DOI
https://doi.org/10.1021/acs.orglett.4c03802
Citations
4
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
1.00

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article

Catalytic Aldehyde–Alkyne Couplings Triggered by Ketyl Radicals

Huan‐Ming Huang, Zhi-Xi Xing, Shu-sheng Chen
4 citations
Organic Letters
Radical Photochemical Reactions
1.00
article

Catalytic Aldehyde–Alkyne Couplings Triggered by Ketyl Radicals

Huan‐Ming Huang, Zhi-Xi Xing, Shu-sheng Chen
article en
4 citations

Abstract

A general and flexible platform for catalytic aldehyde-alkyne couplings triggered by ketyl radicals is described. This open-shell strategy necessitates only a catalytic quantity of a photoredox catalyst, along with Hünig's base (DIPEA) as a halogen atom transfer reagent. The reaction proceeds through sequential steps involving activation, halogen atom transfer, and radical addition. This carbonyl-alkyne coupling exhibits a wide substrate scope and functional group compatibility and has been successfully applied to the late-stage modification of complex architectures.

Organic LettersVol. 26(46)
ShanghaiTech University (CN)
National Natural Science Foundation of China, ShanghaiTech University
Openalex Percentile: Top 26%
Radical Photochemical Reactions
1.00
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