Stereoselective Nitration of Olefins via Visible-Light-Induced Iron-Complex β-Homolysis

Herein, we develop a green and efficient method for the stereoselective synthesis of nitroolefins with ferric nitrate as the nitration reagent. With a visible-light-induced iron-complex β-homolysis pathway and I<sup>-</sup> as a crucial media for electron transfer and dehydrogenation, a broad scope of nitroolefins including some valuable biorelevant derivatives are achieved in high <i>E</i>-selectivity. The reaction is conveniently controlled by nitrate equivalences, and scale-up experiments in batch and flow indicate excellent practicability for this protocol.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-05-23
DOI
https://doi.org/10.1021/acs.joc.5c00908
Citations
5
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
4.68
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article

Stereoselective Nitration of Olefins via Visible-Light-Induced Iron-Complex β-Homolysis

Ran Xu, Ziyu Gan, Yunhe Jin, Shuyang Liu et al.
5 citations
The Journal of Organic Chemistry
Radical Photochemical Reactions
4.68
article

Stereoselective Nitration of Olefins via Visible-Light-Induced Iron-Complex β-Homolysis

Ran Xu, Ziyu Gan, Yunhe Jin, Shuyang Liu, Ziyang Chen, Ziyi Xu, Zhiyan Xue
article en
5 citations

Abstract

Herein, we develop a green and efficient method for the stereoselective synthesis of nitroolefins with ferric nitrate as the nitration reagent. With a visible-light-induced iron-complex β-homolysis pathway and I<sup>-</sup> as a crucial media for electron transfer and dehydrogenation, a broad scope of nitroolefins including some valuable biorelevant derivatives are achieved in high <i>E</i>-selectivity. The reaction is conveniently controlled by nitrate equivalences, and scale-up experiments in batch and flow indicate excellent practicability for this protocol.

The Journal of Organic ChemistryVol. 90(22)
Dalian University of Technology (CN)
Clean water and sanitation
Openalex Percentile: Top 6%
Radical Photochemical Reactions
4.68
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