{"title":"First Bromide‐Catalyzed Selenylation of 2‐Alkyn‐1‐one O‐Methyloximes Enabled the Synthesis of 4‐Selenylated Isoxazoles","authors":"Jinhui Cai, Zhouting Zeng","doi":"10.1002/adsc.202401477","DOIUrl":null,"url":null,"abstract":"A series of 3,5‐diaryl‐4‐selanylisoxazoles were synthesized in 56‐97% yields (most cases >80% yield), which was first accomplished via bromide‐catalyzed selenylation of 2‐alkyn‐1‐one O‐methyloximes using Se element 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.","PeriodicalId":118,"journal":{"name":"Advanced Synthesis & Catalysis","volume":"86 1","pages":""},"PeriodicalIF":4.4000,"publicationDate":"2025-01-11","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Advanced Synthesis & Catalysis","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/adsc.202401477","RegionNum":2,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, APPLIED","Score":null,"Total":0}
引用次数: 0
Abstract
A series of 3,5‐diaryl‐4‐selanylisoxazoles were synthesized in 56‐97% yields (most cases >80% yield), which was first accomplished via bromide‐catalyzed selenylation of 2‐alkyn‐1‐one O‐methyloximes using Se element 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.
期刊介绍：
Advanced Synthesis & Catalysis (ASC) is the leading primary journal in organic, organometallic, and applied chemistry.
The high impact of ASC can be attributed to the unique focus of the journal, which publishes exciting new results from academic and industrial labs on efficient, practical, and environmentally friendly organic synthesis. While homogeneous, heterogeneous, organic, and enzyme catalysis are key technologies to achieve green synthesis, significant contributions to the same goal by synthesis design, reaction techniques, flow chemistry, and continuous processing, multiphase catalysis, green solvents, catalyst immobilization, and recycling, separation science, and process development are also featured in ASC. The Aims and Scope can be found in the Notice to Authors or on the first page of the table of contents in every issue.
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