A Route to the Mild Synthesis of α-Selenomethylketones via Vinyl Azides

Organic selenium compounds are important molecules with a wide range of applications in pharmaceuticals, organic materials, catalysis, and other fields. Herein, we report the synthesis of α-selenomethylketones through the reaction of vinyl azides with arylselenols and benzylselenol. This protocol has the advantages of releasing only nitrogen as a benign byproduct, using air as an environmentally friendly initiator, a very short duration, mild reaction conditions, and broad substrate compatibility. The results of exploratory studies show that oxygen in the air is used as the initiator to promote this radical cascade reaction.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2025-03-27
DOI
https://doi.org/10.1021/acs.joc.4c03085
Citations
2
Primary Topic
Organoselenium and organotellurium chemistry
Type
article
Field-Weighted Citation Impact
2.61

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article

A Route to the Mild Synthesis of α-Selenomethylketones via Vinyl Azides

Limin Ma, Zhichuan Shi, Fei Yang, Xiaoxiao Li et al.
2 citations
The Journal of Organic Chemistry
Organoselenium and organotellurium chemistry
2.61
article

A Route to the Mild Synthesis of α-Selenomethylketones via Vinyl Azides

Limin Ma, Zhichuan Shi, Fei Yang, Xiaoxiao Li, Shuting Zhang, Wen Gu, Zhigang Zhao
article en
2 citations

Abstract

Organic selenium compounds are important molecules with a wide range of applications in pharmaceuticals, organic materials, catalysis, and other fields. Herein, we report the synthesis of α-selenomethylketones through the reaction of vinyl azides with arylselenols and benzylselenol. This protocol has the advantages of releasing only nitrogen as a benign byproduct, using air as an environmentally friendly initiator, a very short duration, mild reaction conditions, and broad substrate compatibility. The results of exploratory studies show that oxygen in the air is used as the initiator to promote this radical cascade reaction.

The Journal of Organic ChemistryVol. 90(14)
State Ethnic Affairs Commission (CN), Southwest Minzu University (CN)
Southwest Minzu University
Openalex Percentile: Top 13%
Organoselenium and organotellurium chemistry
2.61
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