Mild and Selective Oxidation of 4-Alkylpyridines to 4-Acylpyridines under an Oxygen Atmosphere

We report the exclusive conversion of 4-alkylpyridines to 4-acylpyridines. The reaction relies on the selective dearomatization of 4-alkylpyridines to the corresponding alkylidene dihydropyridines, which are oxidized under an oxygen atmosphere. This reaction avoids the use of metal catalysts and elevated temperatures and does not form ketones from 2- or 3-alkylpyridines or diactivated methylene.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-05-12
DOI
https://doi.org/10.1021/acs.joc.6c00173
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Mild and Selective Oxidation of 4-Alkylpyridines to 4-Acylpyridines under an Oxygen Atmosphere

Ekadashi Pradhan, Matthew Puzhitsky, Faizan Rasheed, Tao Zeng et al.
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Mild and Selective Oxidation of 4-Alkylpyridines to 4-Acylpyridines under an Oxygen Atmosphere

Ekadashi Pradhan, Matthew Puzhitsky, Faizan Rasheed, Tao Zeng, Andrei Nikolaev, Brian Doan, Arturo Orellana
article en

Abstract

We report the exclusive conversion of 4-alkylpyridines to 4-acylpyridines. The reaction relies on the selective dearomatization of 4-alkylpyridines to the corresponding alkylidene dihydropyridines, which are oxidized under an oxygen atmosphere. This reaction avoids the use of metal catalysts and elevated temperatures and does not form ketones from 2- or 3-alkylpyridines or diactivated methylene.

The Journal of Organic Chemistry
York University (CA)
Openalex Percentile: Top 9%
Catalytic C–H Functionalization Methods
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