Free-Radical-Promoted β-C-H Functionalization of Simple Aliphatic Ketones, Esters, and Acids with Quinones

Aliphatic ketones, esters, and acids are fundamental chemical raw materials in organic synthesis. The direct site-selective functionalization of such chemicals is attractive but challenging. Herein, we report a free-radical-promoted β-C-H dehydrogenative coupling reaction of simple aliphatic ketones, esters, and acids with quinones. This protocol provides a new method for the β-C-H functionalization of simple aliphatic carbonyl compounds without the assistance of exogenous directing groups and transition metals, which is different from those observed in traditional methods. In addition, the reaction realizes the challenging β-C-C bond formation of aliphatic ketones, esters, and acids, offering a promising strategy for selective alkylation of quinones.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-03-24
DOI
https://doi.org/10.1021/acs.joc.5c03182
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
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article

Free-Radical-Promoted β-C-H Functionalization of Simple Aliphatic Ketones, Esters, and Acids with Quinones

The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Free-Radical-Promoted β-C-H Functionalization of Simple Aliphatic Ketones, Esters, and Acids with Quinones

article en

Abstract

Aliphatic ketones, esters, and acids are fundamental chemical raw materials in organic synthesis. The direct site-selective functionalization of such chemicals is attractive but challenging. Herein, we report a free-radical-promoted β-C-H dehydrogenative coupling reaction of simple aliphatic ketones, esters, and acids with quinones. This protocol provides a new method for the β-C-H functionalization of simple aliphatic carbonyl compounds without the assistance of exogenous directing groups and transition metals, which is different from those observed in traditional methods. In addition, the reaction realizes the challenging β-C-C bond formation of aliphatic ketones, esters, and acids, offering a promising strategy for selective alkylation of quinones.

The Journal of Organic Chemistry
Shandong University of Technology (CN)
Openalex Percentile: Top 10%
Catalytic C–H Functionalization Methods
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