通过可见光光催化和路易斯酸催化协同作用实现无还原剂对映体选择性氮杂-变形反应

IF 16.1 1区 化学 Q1 CHEMISTRY, MULTIDISCIPLINARY
Mingyi Jiang, Zengcheng Yu, Linhan Yang, Fei Wang, Weidi Cao, Xiaohua Liu, Xiaoming Feng
{"title":"通过可见光光催化和路易斯酸催化协同作用实现无还原剂对映体选择性氮杂-变形反应","authors":"Mingyi Jiang, Zengcheng Yu, Linhan Yang, Fei Wang, Weidi Cao, Xiaohua Liu, Xiaoming Feng","doi":"10.1002/anie.202500756","DOIUrl":null,"url":null,"abstract":"Classical aza-Reformatsky reaction generally involves excess reductants. Herein, we developed a visible light-induced catalytic asymmetric aza-Reformatsky reaction via a chiral Lewis acid-assisted direct excitation of imines without additional reductants, enabling the carbon–iodine bond cleavage of iododifluoromethyl ketones and the subsequent enantioselective radical coupling. This protocol provided an ingenious access to chiral β-amino ketones containing a gem-difluorine moiety. The mechanistic studies including radical trapping experiment, electron paramagnetic resonance experiment, cyclic voltammetry experiment and spectroscopic analysis rationalized the reaction process.","PeriodicalId":125,"journal":{"name":"Angewandte Chemie International Edition","volume":"10 1","pages":""},"PeriodicalIF":16.1000,"publicationDate":"2025-02-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Reductant-Free Enantioselective Aza-Reformatsky Reaction Enabled by Synergistic Visible Light Photocatalysis and Lewis Acid Catalysis\",\"authors\":\"Mingyi Jiang, Zengcheng Yu, Linhan Yang, Fei Wang, Weidi Cao, Xiaohua Liu, Xiaoming Feng\",\"doi\":\"10.1002/anie.202500756\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"Classical aza-Reformatsky reaction generally involves excess reductants. Herein, we developed a visible light-induced catalytic asymmetric aza-Reformatsky reaction via a chiral Lewis acid-assisted direct excitation of imines without additional reductants, enabling the carbon–iodine bond cleavage of iododifluoromethyl ketones and the subsequent enantioselective radical coupling. This protocol provided an ingenious access to chiral β-amino ketones containing a gem-difluorine moiety. The mechanistic studies including radical trapping experiment, electron paramagnetic resonance experiment, cyclic voltammetry experiment and spectroscopic analysis rationalized the reaction process.\",\"PeriodicalId\":125,\"journal\":{\"name\":\"Angewandte Chemie International Edition\",\"volume\":\"10 1\",\"pages\":\"\"},\"PeriodicalIF\":16.1000,\"publicationDate\":\"2025-02-18\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Angewandte Chemie International Edition\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1002/anie.202500756\",\"RegionNum\":1,\"RegionCategory\":\"化学\",\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"Q1\",\"JCRName\":\"CHEMISTRY, MULTIDISCIPLINARY\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Angewandte Chemie International Edition","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1002/anie.202500756","RegionNum":1,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q1","JCRName":"CHEMISTRY, MULTIDISCIPLINARY","Score":null,"Total":0}
引用次数: 0

摘要

本文章由计算机程序翻译,如有差异,请以英文原文为准。
Reductant-Free Enantioselective Aza-Reformatsky Reaction Enabled by Synergistic Visible Light Photocatalysis and Lewis Acid Catalysis
Classical aza-Reformatsky reaction generally involves excess reductants. Herein, we developed a visible light-induced catalytic asymmetric aza-Reformatsky reaction via a chiral Lewis acid-assisted direct excitation of imines without additional reductants, enabling the carbon–iodine bond cleavage of iododifluoromethyl ketones and the subsequent enantioselective radical coupling. This protocol provided an ingenious access to chiral β-amino ketones containing a gem-difluorine moiety. The mechanistic studies including radical trapping experiment, electron paramagnetic resonance experiment, cyclic voltammetry experiment and spectroscopic analysis rationalized the reaction process.
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
CiteScore
26.60
自引率
6.60%
发文量
3549
审稿时长
1.5 months
期刊介绍: Angewandte Chemie, a journal of the German Chemical Society (GDCh), maintains a leading position among scholarly journals in general chemistry with an impressive Impact Factor of 16.6 (2022 Journal Citation Reports, Clarivate, 2023). Published weekly in a reader-friendly format, it features new articles almost every day. Established in 1887, Angewandte Chemie is a prominent chemistry journal, offering a dynamic blend of Review-type articles, Highlights, Communications, and Research Articles on a weekly basis, making it unique in the field.
×
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