pd催化富电子杂芳烃的CH(苯磺酰基)二氟甲基化

IF 1.5 4区 化学 Q3 CHEMISTRY, ORGANIC
Zi-En Liu , Tao Lin , Yue Zhao, Jun Cao
{"title":"pd催化富电子杂芳烃的CH(苯磺酰基)二氟甲基化","authors":"Zi-En Liu ,&nbsp;Tao Lin ,&nbsp;Yue Zhao,&nbsp;Jun Cao","doi":"10.1016/j.tetlet.2025.155486","DOIUrl":null,"url":null,"abstract":"<div><div>A novel Pd(0)-catalyzed C<img>H (phenylsulfonyl)difluoromethylation of electron-rich heteroarenes has been developed. The reaction utilizing PhSO<sub>2</sub>CF<sub>2</sub>I as a (phenylsulfonyl)difluoromethylation reagent proceeds efficiently. Mechanistic studies indicate that the C<img>H (phenylsulfonyl)difluoromethylation occurs <em>via</em> a radical pathway. This method demonstrates broad substrate compatibility, including a variety of heterocycles containing nitrogen, oxygen, and sulfur atoms, achieving excellent yields. This study provides an efficient and versatile approach for synthesizing (phenylsulfonyl)difluoromethylated heterocycles, which are valuable in pharmaceuticals, agrochemicals, and materials. The mild reaction conditions and high efficiency of this method make it a promising tool for expanding the scope of organofluorine chemistry applications.</div></div>","PeriodicalId":438,"journal":{"name":"Tetrahedron Letters","volume":"158 ","pages":"Article 155486"},"PeriodicalIF":1.5000,"publicationDate":"2025-02-05","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Pd-catalyzed CH (phenylsulfonyl)difluoromethylation of electron-rich heteroarenes\",\"authors\":\"Zi-En Liu ,&nbsp;Tao Lin ,&nbsp;Yue Zhao,&nbsp;Jun Cao\",\"doi\":\"10.1016/j.tetlet.2025.155486\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>A novel Pd(0)-catalyzed C<img>H (phenylsulfonyl)difluoromethylation of electron-rich heteroarenes has been developed. The reaction utilizing PhSO<sub>2</sub>CF<sub>2</sub>I as a (phenylsulfonyl)difluoromethylation reagent proceeds efficiently. Mechanistic studies indicate that the C<img>H (phenylsulfonyl)difluoromethylation occurs <em>via</em> a radical pathway. This method demonstrates broad substrate compatibility, including a variety of heterocycles containing nitrogen, oxygen, and sulfur atoms, achieving excellent yields. This study provides an efficient and versatile approach for synthesizing (phenylsulfonyl)difluoromethylated heterocycles, which are valuable in pharmaceuticals, agrochemicals, and materials. The mild reaction conditions and high efficiency of this method make it a promising tool for expanding the scope of organofluorine chemistry applications.</div></div>\",\"PeriodicalId\":438,\"journal\":{\"name\":\"Tetrahedron Letters\",\"volume\":\"158 \",\"pages\":\"Article 155486\"},\"PeriodicalIF\":1.5000,\"publicationDate\":\"2025-02-05\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S0040403925000358\",\"RegionNum\":4,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q3\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron Letters","FirstCategoryId":"92","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S0040403925000358","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q3","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

摘要

研究了一种新的Pd(0)催化富电子杂芳烃的苯磺酰二氟甲基化反应。利用PhSO2CF2I作为(苯基磺酰基)二氟甲基化试剂的反应进行得很有效。机理研究表明,CH(苯磺酰基)二氟甲基化是通过自由基途径发生的。该方法具有广泛的底物相容性,包括各种含氮、氧和硫原子的杂环,获得了优异的产率。本研究为合成(苯基磺酰基)二氟甲基化杂环提供了一种高效、通用的方法,在医药、农用化学品和材料等领域具有重要价值。该方法反应条件温和,效率高,是扩大有机氟化学应用范围的一种很有前途的工具。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Pd-catalyzed CH (phenylsulfonyl)difluoromethylation of electron-rich heteroarenes

Pd-catalyzed CH (phenylsulfonyl)difluoromethylation of electron-rich heteroarenes
A novel Pd(0)-catalyzed CH (phenylsulfonyl)difluoromethylation of electron-rich heteroarenes has been developed. The reaction utilizing PhSO2CF2I as a (phenylsulfonyl)difluoromethylation reagent proceeds efficiently. Mechanistic studies indicate that the CH (phenylsulfonyl)difluoromethylation occurs via a radical pathway. This method demonstrates broad substrate compatibility, including a variety of heterocycles containing nitrogen, oxygen, and sulfur atoms, achieving excellent yields. This study provides an efficient and versatile approach for synthesizing (phenylsulfonyl)difluoromethylated heterocycles, which are valuable in pharmaceuticals, agrochemicals, and materials. The mild reaction conditions and high efficiency of this method make it a promising tool for expanding the scope of organofluorine chemistry applications.
求助全文
通过发布文献求助,成功后即可免费获取论文全文。 去求助
来源期刊
Tetrahedron Letters
Tetrahedron Letters 化学-有机化学
CiteScore
3.50
自引率
5.60%
发文量
521
审稿时长
28 days
期刊介绍: Tetrahedron Letters provides maximum dissemination of outstanding developments in organic chemistry. The journal is published weekly and covers developments in techniques, structures, methods and conclusions in experimental and theoretical organic chemistry. Rapid publication of timely and significant research results enables researchers from all over the world to transmit quickly their new contributions to large, international audiences.
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
确定
请完成安全验证×
copy
已复制链接
快去分享给好友吧!
我知道了
右上角分享
点击右上角分享
0
联系我们:info@booksci.cn Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。 Copyright © 2023 布克学术 All rights reserved.
京ICP备2023020795号-1
ghs 京公网安备 11010802042870号
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术官方微信