通过氢原子转移,光氧化还原催化n -三氟乙基羟胺或羟酰胺中C(sp3)-H键烯丙基化。

IF 2.7 3区 化学 Q1 CHEMISTRY, ORGANIC
Jia-Yin Wang, Jin-Long Dai, Tao Wang, Ming-Xian Zhang, Hong-Kai Sha, Shenghu Yan
{"title":"通过氢原子转移,光氧化还原催化n -三氟乙基羟胺或羟酰胺中C(sp3)-H键烯丙基化。","authors":"Jia-Yin Wang, Jin-Long Dai, Tao Wang, Ming-Xian Zhang, Hong-Kai Sha, Shenghu Yan","doi":"10.1039/d5ob01288k","DOIUrl":null,"url":null,"abstract":"<p><p>Herein, we present an organophotoredox-catalyzed nitrogen-centered radical-triggered allylation reaction that enables the synthesis of trisubstituted alkenes from MBH adducts and <i>N</i>-trifluoroethylhydroxylamine reagents or hydroxamides <i>via</i> a hydrogen atom transfer (HAT) strategy. When <i>N</i>-trifluoroethylhydroxylamine reagents were employed as radical precursors, various homoallylic α-trifluoromethylamines were generated through 1,2-HAT of the <i>in situ</i>-generated <i>N</i>-trifluoroethyl radicals. Moreover, a series of hydroxamides (1,5-HAT reagents) could be tolerated by this catalytic system, affording the corresponding alkyl amides with excellent yields.</p>","PeriodicalId":96,"journal":{"name":"Organic & Biomolecular Chemistry","volume":" ","pages":""},"PeriodicalIF":2.7000,"publicationDate":"2025-09-26","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Photoredox-catalyzed allylation of C(sp<sup>3</sup>)-H bonds in <i>N</i>-trifluoroethyl hydroxylamines or hydroxamides <i>via</i> hydrogen atom transfer.\",\"authors\":\"Jia-Yin Wang, Jin-Long Dai, Tao Wang, Ming-Xian Zhang, Hong-Kai Sha, Shenghu Yan\",\"doi\":\"10.1039/d5ob01288k\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>Herein, we present an organophotoredox-catalyzed nitrogen-centered radical-triggered allylation reaction that enables the synthesis of trisubstituted alkenes from MBH adducts and <i>N</i>-trifluoroethylhydroxylamine reagents or hydroxamides <i>via</i> a hydrogen atom transfer (HAT) strategy. When <i>N</i>-trifluoroethylhydroxylamine reagents were employed as radical precursors, various homoallylic α-trifluoromethylamines were generated through 1,2-HAT of the <i>in situ</i>-generated <i>N</i>-trifluoroethyl radicals. Moreover, a series of hydroxamides (1,5-HAT reagents) could be tolerated by this catalytic system, affording the corresponding alkyl amides with excellent yields.</p>\",\"PeriodicalId\":96,\"journal\":{\"name\":\"Organic & Biomolecular Chemistry\",\"volume\":\" \",\"pages\":\"\"},\"PeriodicalIF\":2.7000,\"publicationDate\":\"2025-09-26\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic & Biomolecular Chemistry\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1039/d5ob01288k\",\"RegionNum\":3,\"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 & Biomolecular Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1039/d5ob01288k","RegionNum":3,"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

在此,我们提出了一个有机光氧化还原催化的氮中心自由基触发的烯丙化反应,该反应可以通过氢原子转移(HAT)策略从MBH加合物和n-三氟乙基羟胺试剂或羟酰胺合成三取代烯烃。当n -三氟乙基羟胺试剂作为自由基前体时,通过原位生成的n -三氟乙基自由基的1,2- hat生成各种同烯丙基α-三氟甲基胺。此外,该催化体系还能耐受一系列羟基酰胺(1,5- hat试剂),生成相应的烷基酰胺,产率高。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
Photoredox-catalyzed allylation of C(sp3)-H bonds in N-trifluoroethyl hydroxylamines or hydroxamides via hydrogen atom transfer.

Herein, we present an organophotoredox-catalyzed nitrogen-centered radical-triggered allylation reaction that enables the synthesis of trisubstituted alkenes from MBH adducts and N-trifluoroethylhydroxylamine reagents or hydroxamides via a hydrogen atom transfer (HAT) strategy. When N-trifluoroethylhydroxylamine reagents were employed as radical precursors, various homoallylic α-trifluoromethylamines were generated through 1,2-HAT of the in situ-generated N-trifluoroethyl radicals. Moreover, a series of hydroxamides (1,5-HAT reagents) could be tolerated by this catalytic system, affording the corresponding alkyl amides with excellent yields.

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 & Biomolecular Chemistry
Organic & Biomolecular Chemistry 化学-有机化学
CiteScore
5.50
自引率
9.40%
发文量
1056
审稿时长
1.3 months
期刊介绍: Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.
×
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