Ruthenium-Catalyzed Decarboxylative Direct 2-Pyridination of α,β-Unsaturated Carboxylic Acids

We report a ruthenium-catalyzed decarboxylative direct mono-2-pyridination of α,β-unsaturated carboxylic acids, offering a selective method for synthesizing 2-(1-arylalkenyl)pyridines. Under redox-neutral conditions, the reaction demonstrates broad substrate scope, high functional group tolerance, and significant potential for further derivatization. Mechanistic studies reveal that selective activation of the allylic C(sp<sup>3</sup>)-H bond, directed by the pyridine group, underpins the observed mono-2-pyridination. This work provides an efficient and selective strategy for the catalytic decarboxylative transformation of α,β-unsaturated carboxylic acids, expanding the toolbox for functionalizing pyridine derivatives.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-05-19
DOI
https://doi.org/10.1021/acs.joc.5c00375
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

Ruthenium-Catalyzed Decarboxylative Direct 2-Pyridination of α,β-Unsaturated Carboxylic Acids

Ying Zhu, Jing Zhang, Jiaojiao Guo
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Ruthenium-Catalyzed Decarboxylative Direct 2-Pyridination of α,β-Unsaturated Carboxylic Acids

Ying Zhu, Jing Zhang, Jiaojiao Guo
article en

Abstract

We report a ruthenium-catalyzed decarboxylative direct mono-2-pyridination of α,β-unsaturated carboxylic acids, offering a selective method for synthesizing 2-(1-arylalkenyl)pyridines. Under redox-neutral conditions, the reaction demonstrates broad substrate scope, high functional group tolerance, and significant potential for further derivatization. Mechanistic studies reveal that selective activation of the allylic C(sp<sup>3</sup>)-H bond, directed by the pyridine group, underpins the observed mono-2-pyridination. This work provides an efficient and selective strategy for the catalytic decarboxylative transformation of α,β-unsaturated carboxylic acids, expanding the toolbox for functionalizing pyridine derivatives.

The Journal of Organic ChemistryVol. 90(21)
Wuhan University (CN)
National Natural Science Foundation of China, Wuhan University, Fundamental Research Funds for the Central Universities
Openalex Percentile: Top 92%
Catalytic C–H Functionalization Methods
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