The Catalytic Synthesis of α-Bromo Aryl Acetic Acids by Late-Stage Bromination

IF 2.5 3区 化学 Q2 CHEMISTRY, ORGANIC
Junyu Wang, Xin Wu, Beining Wang, Xiangyang Yuan, Shengnan Yang, Haipeng Hu
{"title":"The Catalytic Synthesis of α-Bromo Aryl Acetic Acids by Late-Stage Bromination","authors":"Junyu Wang, Xin Wu, Beining Wang, Xiangyang Yuan, Shengnan Yang, Haipeng Hu","doi":"10.1002/ejoc.202400962","DOIUrl":null,"url":null,"abstract":"We report a catalytic late-stage bromination strategy for the α-C-H functionalization of aryl acetic acid. The aryl acetic acid was transformed into enediolate in the presence of an (AcO)4B2O with the combination of DBU, and consequently underwent an electrophilic bromination reaction with pyridinium tribromide. A wide range of α-bromo aryl acetic acids were isolated in yields of 19-65%. In addition, the reaction could be performed on a gram scale, and several transformations of the products were carried out.","PeriodicalId":167,"journal":{"name":"European Journal of Organic Chemistry","volume":null,"pages":null},"PeriodicalIF":2.5000,"publicationDate":"2024-11-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"European Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/ejoc.202400962","RegionNum":3,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

Abstract

We report a catalytic late-stage bromination strategy for the α-C-H functionalization of aryl acetic acid. The aryl acetic acid was transformed into enediolate in the presence of an (AcO)4B2O with the combination of DBU, and consequently underwent an electrophilic bromination reaction with pyridinium tribromide. A wide range of α-bromo aryl acetic acids were isolated in yields of 19-65%. In addition, the reaction could be performed on a gram scale, and several transformations of the products were carried out.
通过后期溴化催化合成α-溴芳基乙酸
我们报告了一种催化后期溴化策略,用于芳基乙酸的 α-C-H 功能化。芳基乙酸在 (AcO)4B2O 和 DBU 的作用下转化为烯二醇,然后与三溴化吡啶发生亲电溴化反应。分离出多种 α-溴芳基乙酸,产率为 19-65%。此外,该反应可在克级规模上进行,并对产物进行了多次转化。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
CiteScore
5.40
自引率
3.60%
发文量
752
审稿时长
1 months
期刊介绍: The European Journal of Organic Chemistry (2019 ISI Impact Factor 2.889) publishes Full Papers, Communications, and Minireviews from the entire spectrum of synthetic organic, bioorganic and physical-organic chemistry. It is published on behalf of Chemistry Europe, an association of 16 European chemical societies. The following journals have been merged to form two leading journals, the European Journal of Organic Chemistry and the European Journal of Inorganic Chemistry: Liebigs Annalen Bulletin des Sociétés Chimiques Belges Bulletin de la Société Chimique de France Gazzetta Chimica Italiana Recueil des Travaux Chimiques des Pays-Bas Anales de Química Chimika Chronika Revista Portuguesa de Química ACH—Models in Chemistry Polish Journal of Chemistry.
×
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