联合光氧化还原和碳烯催化:通过持续自由基效应的烯烃硼羰基化

IF 4.7 1区 化学 Q1 CHEMISTRY, ORGANIC
Xiaochen Wang, Senhui Wu, Hongyu Zhang, Qingmin Wang, Shu-Rong Ban
{"title":"联合光氧化还原和碳烯催化:通过持续自由基效应的烯烃硼羰基化","authors":"Xiaochen Wang, Senhui Wu, Hongyu Zhang, Qingmin Wang, Shu-Rong Ban","doi":"10.1039/d5qo00819k","DOIUrl":null,"url":null,"abstract":"Herein, we report a mild and operationally simple dual-catalytic method for the synthesis of <em>β</em>-boryl carbonyl compounds via alkene difunctionalization. Specifically, combining <em>N</em>-heterocyclic carbene catalysis and photocatalysis enables a three-component radical cross-coupling reaction between a wide range of feedstock carboxylic acids, easily prepared NHC-boranes, and readily available alkenes to yield structurally diverse <em>β</em>-boryl carbonyl compounds. Longer lifetime ketyl radicals facilitate efficient boron participation in the coupling through the persistent radical effect. The method could be used to install acyl and borane groups on highly functionalized natural-product-derived compounds without pre–activation in one step and most products show good diastereoselectivity.","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":"51 1","pages":""},"PeriodicalIF":4.7000,"publicationDate":"2025-07-16","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Combined Photoredox and Carbene Catalysis: Alkene Borocarbonylation via the Persistent Radical Effect\",\"authors\":\"Xiaochen Wang, Senhui Wu, Hongyu Zhang, Qingmin Wang, Shu-Rong Ban\",\"doi\":\"10.1039/d5qo00819k\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Herein, we report a mild and operationally simple dual-catalytic method for the synthesis of <em>β</em>-boryl carbonyl compounds via alkene difunctionalization. Specifically, combining <em>N</em>-heterocyclic carbene catalysis and photocatalysis enables a three-component radical cross-coupling reaction between a wide range of feedstock carboxylic acids, easily prepared NHC-boranes, and readily available alkenes to yield structurally diverse <em>β</em>-boryl carbonyl compounds. Longer lifetime ketyl radicals facilitate efficient boron participation in the coupling through the persistent radical effect. The method could be used to install acyl and borane groups on highly functionalized natural-product-derived compounds without pre–activation in one step and most products show good diastereoselectivity.\",\"PeriodicalId\":97,\"journal\":{\"name\":\"Organic Chemistry Frontiers\",\"volume\":\"51 1\",\"pages\":\"\"},\"PeriodicalIF\":4.7000,\"publicationDate\":\"2025-07-16\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Chemistry Frontiers\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d5qo00819k\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, ORGANIC\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d5qo00819k","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

摘要

本文报道了一种温和、操作简单的双催化烯烃双官能化合成β-硼基羰基化合物的方法。具体而言,结合n -杂环羰基催化和光催化,可以在广泛的原料羧酸、易于制备的nhc -硼烷和易得的烯烃之间进行三组分自由基交叉偶联反应,生成结构多样的β-硼基羰基化合物。寿命较长的基自由基通过持续自由基效应促进硼有效参与偶联。该方法无需预活化即可在高功能化天然产物衍生化合物上安装酰基和硼烷基团,且大多数产物具有良好的非对映选择性。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Combined Photoredox and Carbene Catalysis: Alkene Borocarbonylation via the Persistent Radical Effect
Herein, we report a mild and operationally simple dual-catalytic method for the synthesis of β-boryl carbonyl compounds via alkene difunctionalization. Specifically, combining N-heterocyclic carbene catalysis and photocatalysis enables a three-component radical cross-coupling reaction between a wide range of feedstock carboxylic acids, easily prepared NHC-boranes, and readily available alkenes to yield structurally diverse β-boryl carbonyl compounds. Longer lifetime ketyl radicals facilitate efficient boron participation in the coupling through the persistent radical effect. The method could be used to install acyl and borane groups on highly functionalized natural-product-derived compounds without pre–activation in one step and most products show good diastereoselectivity.
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
Organic Chemistry Frontiers
Organic Chemistry Frontiers CHEMISTRY, ORGANIC-
CiteScore
7.90
自引率
11.10%
发文量
686
审稿时长
1 months
期刊介绍: Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic 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:604180095
Book学术官方微信