Photoinduced oxidation of benzylic boronic esters to ketones/aldehydes via α-borylalkyl radicals†

Zhijun Wang , Lanfeng Wei , Jichang Liu , Yu Wei , Liang Xu
{"title":"Photoinduced oxidation of benzylic boronic esters to ketones/aldehydes via α-borylalkyl radicals†","authors":"Zhijun Wang ,&nbsp;Lanfeng Wei ,&nbsp;Jichang Liu ,&nbsp;Yu Wei ,&nbsp;Liang Xu","doi":"10.1039/d2qo01457b","DOIUrl":null,"url":null,"abstract":"<div><p>A method for direct oxidation of boronic esters to the carbonyl groups has been established herein. Under the irradiation of visible light and O<sub>2</sub> atmosphere, ketones and aldehydes can be obtained in moderate to excellent yields. Using tetrabutylammonium tribromide (TBATB) as the catalyst, this procedure avoids using of metal-based (photo)catalysts. α-Borylalkyl radicals have been proposed as the key intermediates of this oxidation process.</p></div>","PeriodicalId":94379,"journal":{"name":"Organic chemistry frontiers : an international journal of organic chemistry","volume":"10 1","pages":"Pages 104-108"},"PeriodicalIF":0.0000,"publicationDate":"2023-01-01","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic chemistry frontiers : an international journal of organic chemistry","FirstCategoryId":"1085","ListUrlMain":"https://www.sciencedirect.com/org/science/article/pii/S2052411023003279","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0

Abstract

A method for direct oxidation of boronic esters to the carbonyl groups has been established herein. Under the irradiation of visible light and O2 atmosphere, ketones and aldehydes can be obtained in moderate to excellent yields. Using tetrabutylammonium tribromide (TBATB) as the catalyst, this procedure avoids using of metal-based (photo)catalysts. α-Borylalkyl radicals have been proposed as the key intermediates of this oxidation process.

Abstract Image

通过α-硼基自由基†光诱导苯硼酯氧化生成酮/醛
本文建立了一种硼酯直接氧化羰基的方法。在可见光和O2气氛的照射下,可以得到中高收率的酮类和醛类化合物。采用四丁基三溴化铵(TBATB)作为催化剂,避免了金属基(光)催化剂的使用。α-硼烷基自由基被认为是该氧化过程的关键中间体。
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
7.80
自引率
0.00%
发文量
0
×
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