Dicarbofunctionalization of Vinylarenes with Pyridine and Aldehydes via Photocatalytic Hydrogen Atom Transfer

We describe a metal-free and mild three-component reaction utilizing vinylarenes, alkyl aldehydes, and 4-cyanopyridine. In this reaction, the scope of vinylarenes and alkyl aldehydes includes over 40 examples, generating a variety of β-pyridinyl ketones. Moreover, potential applications of this method have been demonstrated by the functionalization of pharmaceutical molecules. An acyl radical is proposed to be produced via a polarity-matched hydrogen atom transfer between alkyl aldehydes and a triplet-state diradical from benzophenone.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2024-10-14
DOI
https://doi.org/10.1021/acs.joc.4c02016
Citations
6
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
1.50

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article

Dicarbofunctionalization of Vinylarenes with Pyridine and Aldehydes via Photocatalytic Hydrogen Atom Transfer

Yi Zhou, Bin Liu, Junhua Xu
6 citations
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
1.50
article

Dicarbofunctionalization of Vinylarenes with Pyridine and Aldehydes via Photocatalytic Hydrogen Atom Transfer

Yi Zhou, Bin Liu, Junhua Xu
article en
6 citations

Abstract

We describe a metal-free and mild three-component reaction utilizing vinylarenes, alkyl aldehydes, and 4-cyanopyridine. In this reaction, the scope of vinylarenes and alkyl aldehydes includes over 40 examples, generating a variety of β-pyridinyl ketones. Moreover, potential applications of this method have been demonstrated by the functionalization of pharmaceutical molecules. An acyl radical is proposed to be produced via a polarity-matched hydrogen atom transfer between alkyl aldehydes and a triplet-state diradical from benzophenone.

The Journal of Organic ChemistryVol. 89(21)
Nanchang University (CN)
Natural Science Foundation of Jiangxi Province, Nanchang University
Clean water and sanitation
Openalex Percentile: Top 19%
Catalytic C–H Functionalization Methods
1.50
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