Photo-Induced, Phenylhydrazine-Promoted Transition-Metal-Free Dehalogenation of Aryl Fluorides, Chlorides, Bromides, and Iodides

In this study, we present a straightforward and highly effective photo-triggered hydrogenation method for aryl halides, devoid of transition-metal catalysts. Through the synergistic utilization of light, PhNHNH2, and a base, we have successfully initiated the desired radical-mediated hydrogenation p...

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Bibliographic Details
Published inMolecules (Basel, Switzerland) Vol. 28; no. 19; p. 6915
Main Authors Zhu, Yiwei, Wu, Zhimin, Sun, Hongcai, Ding, Junjun
Format Journal Article
LanguageEnglish
Published Basel MDPI AG 01.10.2023
MDPI
Subjects
aryl halides
Chlorides
Chromatography
Communication
Dichloropropane
Electrolysis
Experiments
Fluorides
Heterocyclic compounds
Hydrazine
Hydrogenation
Light
NMR
Nuclear magnetic resonance
photo-induced hydrogenation
Pressure vessels
radical-mediated hydrogenation
Solvents
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Summary:In this study, we present a straightforward and highly effective photo-triggered hydrogenation method for aryl halides, devoid of transition-metal catalysts. Through the synergistic utilization of light, PhNHNH2, and a base, we have successfully initiated the desired radical-mediated hydrogenation process. Remarkably, utilizing mild reaction conditions, a wide range of aryl halides, including fluorides, chlorides, bromides, and iodides, can be selectively transformed into their corresponding (hetero)arene counterparts, with exceptional yields. Additionally, this approach demonstrates a remarkable compatibility with diverse functional groups and heterocyclic compounds, highlighting its versatility and potential for use in various chemical transformations.
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28196915