烯丙基醚的电化学二溴乙酰氧基化和三卤化反应

Yong Jiang , Fumei Ke , Chen Zhu , Daixi Li , Tao Shen
{"title":"烯丙基醚的电化学二溴乙酰氧基化和三卤化反应","authors":"Yong Jiang ,&nbsp;Fumei Ke ,&nbsp;Chen Zhu ,&nbsp;Daixi Li ,&nbsp;Tao Shen","doi":"10.1016/j.tchem.2024.100106","DOIUrl":null,"url":null,"abstract":"<div><div>Trifunctionalization serves as an efficient method for rapidly enhancing molecular complexity by incorporating three functional groups from simple, readily available raw materials. Herein, we describe an electrochemical trifunctionalization protocol for allylarenes that enables the synthesis of a diverse range of dibromoacetoxylated and trihalogenated products. Further gram-scale synthesis and divergent transformation of products demonstrate potential application in the pharmaceutical industry. Mechanistic studies reveal the process involves a cascade oxidative difunctionalization of C<img>C bond and oxidative functionalization of benzylic C–H bond.</div></div>","PeriodicalId":74918,"journal":{"name":"Tetrahedron chem","volume":"12 ","pages":"Article 100106"},"PeriodicalIF":0.0000,"publicationDate":"2024-10-28","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Electrochemical dibromoacetoxylation and trihalogenation of allylarenes\",\"authors\":\"Yong Jiang ,&nbsp;Fumei Ke ,&nbsp;Chen Zhu ,&nbsp;Daixi Li ,&nbsp;Tao Shen\",\"doi\":\"10.1016/j.tchem.2024.100106\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<div><div>Trifunctionalization serves as an efficient method for rapidly enhancing molecular complexity by incorporating three functional groups from simple, readily available raw materials. Herein, we describe an electrochemical trifunctionalization protocol for allylarenes that enables the synthesis of a diverse range of dibromoacetoxylated and trihalogenated products. Further gram-scale synthesis and divergent transformation of products demonstrate potential application in the pharmaceutical industry. Mechanistic studies reveal the process involves a cascade oxidative difunctionalization of C<img>C bond and oxidative functionalization of benzylic C–H bond.</div></div>\",\"PeriodicalId\":74918,\"journal\":{\"name\":\"Tetrahedron chem\",\"volume\":\"12 \",\"pages\":\"Article 100106\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-10-28\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Tetrahedron chem\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://www.sciencedirect.com/science/article/pii/S2666951X24000457\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Tetrahedron chem","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/science/article/pii/S2666951X24000457","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0

摘要

三官能化是一种有效的方法,可通过从简单易得的原材料中加入三个官能团来快速提高分子的复杂性。在此,我们介绍了一种烯丙基醚的电化学三官能化方案,该方案可合成多种二溴乙酰氧基化和三卤化产品。进一步的克级合成和不同产品的转化证明了其在制药行业的潜在应用。机理研究表明,该过程涉及 CC 键的级联氧化双官能化和苄基 C-H 键的氧化官能化。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Electrochemical dibromoacetoxylation and trihalogenation of allylarenes

Electrochemical dibromoacetoxylation and trihalogenation of allylarenes
Trifunctionalization serves as an efficient method for rapidly enhancing molecular complexity by incorporating three functional groups from simple, readily available raw materials. Herein, we describe an electrochemical trifunctionalization protocol for allylarenes that enables the synthesis of a diverse range of dibromoacetoxylated and trihalogenated products. Further gram-scale synthesis and divergent transformation of products demonstrate potential application in the pharmaceutical industry. Mechanistic studies reveal the process involves a cascade oxidative difunctionalization of CC bond and oxidative functionalization of benzylic C–H bond.
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 chem
Tetrahedron chem Organic Chemistry
CiteScore
3.60
自引率
0.00%
发文量
0
审稿时长
27 days
×
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