Visible Light-Induced Divergent Deoxygenation/Hydroxymethylation of Pyridine <i>N</i>-Oxides

This study explores the deoxygenation of pyridine <i>N</i>-oxides and presents a one-step photoredox method for the direct synthesis of 2-hydroxymethylated pyridines from pyridine <i>N</i>-oxides. Mechanism studies elucidate the role of the catalyst and provide evidence of the possible electron transfer process and the formation of key radicals. A range of pyridine derivatives, particularly 2-hydroxymethyl-substituted pyridines, which may be difficult to obtain, can be synthesized in a single step.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-01-10
DOI
https://doi.org/10.1021/acs.joc.4c02770
Citations
4
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
3.74

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article

Visible Light-Induced Divergent Deoxygenation/Hydroxymethylation of Pyridine N-Oxides

Changhao Feng, Hao Guo, Aishun Ding
4 citations
The Journal of Organic Chemistry
Radical Photochemical Reactions
3.74
article

Visible Light-Induced Divergent Deoxygenation/Hydroxymethylation of Pyridine N-Oxides

Changhao Feng, Hao Guo, Aishun Ding
article en
4 citations

Abstract

This study explores the deoxygenation of pyridine <i>N</i>-oxides and presents a one-step photoredox method for the direct synthesis of 2-hydroxymethylated pyridines from pyridine <i>N</i>-oxides. Mechanism studies elucidate the role of the catalyst and provide evidence of the possible electron transfer process and the formation of key radicals. A range of pyridine derivatives, particularly 2-hydroxymethyl-substituted pyridines, which may be difficult to obtain, can be synthesized in a single step.

The Journal of Organic ChemistryVol. 90(3)
Fudan University (CN)
Science and Technology Commission of Shanghai Municipality
Openalex Percentile: Top 9%
Radical Photochemical Reactions
3.74
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