First Bromide‐Catalyzed Selenylation of 2‐Alkyn‐1‐One <i>O</i>‐Methyloximes Enabled the Synthesis of 4‐Selenylated Isoxazoles

Abstract A series of 3,5‐diaryl‐4‐selanylisoxazoles were synthesized in 56–97% yields (most cases&gt;80% yield), which was first accomplished via bromide‐catalyzed selenylation of 2‐alkyn‐1‐one O ‐methyloximes using element Se and boronic acids as the selenyl source. Compared to traditional strategies, this method proceeded under simple catalytic system. Broad substrate scope, good functional group compatibility, metal‐free conditions, and easy operation was showed in this protocol. Additionally, this method was easily amendable to gram‐scale reaction and synthetic transformations. Furthermore, preliminary mechanistic experiments demonstrated that a radical pathway was possibly involved in this work.

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Publication Details

Journal
Advanced Synthesis & Catalysis
Published
2025-01-10
DOI
https://doi.org/10.1002/adsc.202401477
Citations
12
Primary Topic
Organoselenium and organotellurium chemistry
Type
article
Field-Weighted Citation Impact
15.69
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article

First Bromide‐Catalyzed Selenylation of 2‐Alkyn‐1‐One O‐Methyloximes Enabled the Synthesis of 4‐Selenylated Isoxazoles

Jinhui Cai, Zhouting Zeng
12 citations
Advanced Synthesis & Catalysis
Organoselenium and organotellurium chemistry
15.69
article

First Bromide‐Catalyzed Selenylation of 2‐Alkyn‐1‐One O‐Methyloximes Enabled the Synthesis of 4‐Selenylated Isoxazoles

Jinhui Cai, Zhouting Zeng
article en
12 citations

Abstract

Abstract A series of 3,5‐diaryl‐4‐selanylisoxazoles were synthesized in 56–97% yields (most cases&gt;80% yield), which was first accomplished via bromide‐catalyzed selenylation of 2‐alkyn‐1‐one O ‐methyloximes using element Se and boronic acids as the selenyl source. Compared to traditional strategies, this method proceeded under simple catalytic system. Broad substrate scope, good functional group compatibility, metal‐free conditions, and easy operation was showed in this protocol. Additionally, this method was easily amendable to gram‐scale reaction and synthetic transformations. Furthermore, preliminary mechanistic experiments demonstrated that a radical pathway was possibly involved in this work.

Advanced Synthesis & CatalysisVol. 367(4)
University of South China (CN)
Openalex Percentile: Top 1%
Organoselenium and organotellurium chemistry
15.69
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