N-亚磺酰基丙烯酰胺与溴二氟乙酰胺的光氧化自由基 Truce-Smiles 重排反应

IF 4.9 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-12-18 DOI:10.1021/acs.orglett.4c04484
Lin Tian, Pu Chen, Xiaochen Ji, Guo-Jun Deng, Huawen Huang
{"title":"N-亚磺酰基丙烯酰胺与溴二氟乙酰胺的光氧化自由基 Truce-Smiles 重排反应","authors":"Lin Tian, Pu Chen, Xiaochen Ji, Guo-Jun Deng, Huawen Huang","doi":"10.1021/acs.orglett.4c04484","DOIUrl":null,"url":null,"abstract":"We herein report a photochemical Truce–Smiles rearrangement reaction of <i>N</i>-sulfinyl acrylamides with bromodifluoroacetamides resulting in the synthesis of a series of aryl difluoroglutaramides in moderate to good yields. The asymmetric synthesis using chiral sulfinamides produced quaternary carbon<i>-</i>centered glutaramide products with a modest enantioselectivity. This protocol effectively complements previous Truce–Smiles rearrangement methods involving <i>N</i>-sulfonyl acrylamides.","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":"23 1","pages":""},"PeriodicalIF":4.9000,"publicationDate":"2024-12-18","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Photoredox Radical Truce–Smiles Rearrangement of N-Sulfinyl Acrylamides with Bromodifluoroacetamides\",\"authors\":\"Lin Tian, Pu Chen, Xiaochen Ji, Guo-Jun Deng, Huawen Huang\",\"doi\":\"10.1021/acs.orglett.4c04484\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"We herein report a photochemical Truce–Smiles rearrangement reaction of <i>N</i>-sulfinyl acrylamides with bromodifluoroacetamides resulting in the synthesis of a series of aryl difluoroglutaramides in moderate to good yields. The asymmetric synthesis using chiral sulfinamides produced quaternary carbon<i>-</i>centered glutaramide products with a modest enantioselectivity. This protocol effectively complements previous Truce–Smiles rearrangement methods involving <i>N</i>-sulfonyl acrylamides.\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":\"23 1\",\"pages\":\"\"},\"PeriodicalIF\":4.9000,\"publicationDate\":\"2024-12-18\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Organic Letters\",\"FirstCategoryId\":\"92\",\"ListUrlMain\":\"https://doi.org/10.1021/acs.orglett.4c04484\",\"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 Letters","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.1021/acs.orglett.4c04484","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

我们在此报告了 N-亚磺酰基丙烯酰胺与溴二氟乙酰胺的光化学 Truce-Smiles 重排反应,该反应导致一系列芳基二氟戊二酰胺的合成,产率为中等到良好。使用手性亚氨基甲酸酯进行的不对称合成产生了以碳为中心的季戊四酰胺产品,对映选择性适中。该方案有效地补充了以前涉及 N-磺酰基丙烯酰胺的 Truce-Smiles 重排方法。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

摘要图片

查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
Photoredox Radical Truce–Smiles Rearrangement of N-Sulfinyl Acrylamides with Bromodifluoroacetamides
We herein report a photochemical Truce–Smiles rearrangement reaction of N-sulfinyl acrylamides with bromodifluoroacetamides resulting in the synthesis of a series of aryl difluoroglutaramides in moderate to good yields. The asymmetric synthesis using chiral sulfinamides produced quaternary carbon-centered glutaramide products with a modest enantioselectivity. This protocol effectively complements previous Truce–Smiles rearrangement methods involving N-sulfonyl acrylamides.
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 Letters
Organic Letters 化学-有机化学
CiteScore
9.30
自引率
11.50%
发文量
1607
审稿时长
1.5 months
期刊介绍: Organic Letters invites original reports of fundamental research in all branches of the theory and practice of organic, physical organic, organometallic,medicinal, and bioorganic chemistry. Organic Letters provides rapid disclosure of the key elements of significant studies that are of interest to a large portion of the organic community. In selecting manuscripts for publication, the Editors place emphasis on the originality, quality and wide interest of the work. Authors should provide enough background information to place the new disclosure in context and to justify the rapid publication format. Back-to-back Letters will be considered. Full details should be reserved for an Article, which should appear in due course.
期刊最新文献
Photoinduced Pd-Catalyzed 1,4-Dicarbofunctionalization of 1,3-Butadienes via Aliphatic C–H Bond Elaboration Condition-Controlled Rh(III)-Catalyzed Chemodivergent Cyclization of 2-Arylpyridines with CF3-Imidoyl Sulfoxonium Ylides via Triple C–H Activation Visible-Light-Triggered Mn2(CO)10-Catalyzed Carbonylation of (Hetero)aryl Chlorides Pd(OAc)2-Catalyzed Approach to Phenanthridin-6(5H)-one Skeletons Fluorous-Phase- and Chiral-Axis-Enhanced Fluorescent Sensitivity and Chemoselectivity for Cysteine Recognition
×
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
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 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 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1