Photoexcited Nitroarene-Mediated Oxidation Enables the Total Synthesis of (−)-Securingine G

In general, dehydrogenation of piperideine and piperidine to pyridine requires precious transition-metal catalysts or harsh oxidative conditions. In this study, we show that photoexcited triplet-state nitroarenes act as effective dehydrogenation agents for a one-step anaerobic aromatization of these cyclic amines. The utility of this transformation is demonstrated in the second-generation total synthesis of securingine G.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-01-02
DOI
https://doi.org/10.1021/acs.joc.5c02257
Citations
1
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
22.95
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article

Photoexcited Nitroarene-Mediated Oxidation Enables the Total Synthesis of (−)-Securingine G

Sunkyu Han, Valeriia Zvereva
1 citations
The Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
22.95
article

Photoexcited Nitroarene-Mediated Oxidation Enables the Total Synthesis of (−)-Securingine G

Sunkyu Han, Valeriia Zvereva
article en
1 citations

Abstract

In general, dehydrogenation of piperideine and piperidine to pyridine requires precious transition-metal catalysts or harsh oxidative conditions. In this study, we show that photoexcited triplet-state nitroarenes act as effective dehydrogenation agents for a one-step anaerobic aromatization of these cyclic amines. The utility of this transformation is demonstrated in the second-generation total synthesis of securingine G.

The Journal of Organic ChemistryVol. 91(2)
Korea Advanced Institute of Science and Technology (KR)
Openalex Percentile: Top 3%
Catalytic C–H Functionalization Methods
22.95
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