通过 Ylide 形成和 1,4-磺酰基重排对碳化铑进行氨磺酰化。

IF 4.9 1区 化学 Q1 CHEMISTRY, ORGANIC
Jiahui Su, Meirong Huang, Zichun Yan, Shengbiao Tang, Xinhao Zhang, Jiangtao Sun
{"title":"通过 Ylide 形成和 1,4-磺酰基重排对碳化铑进行氨磺酰化。","authors":"Jiahui Su, Meirong Huang, Zichun Yan, Shengbiao Tang, Xinhao Zhang, Jiangtao Sun","doi":"10.1021/acs.orglett.4c03733","DOIUrl":null,"url":null,"abstract":"<p><p>We report here the use of pyridin-2-yl benzenesulfonates as sulfonylation reagents in a difunctionalization reaction based on oxy-pyridinium ylide chemistry, providing an effective protocol for the installation of both a sulfonyl group and a pyridone moiety into one molecule. Density functional theory (DFT) calculations disclose that the reaction process might proceed through sequential metal-bound ylide formation, keto-enol tautomerism, and the migratory rearrangement of the sulfonyl group.</p>","PeriodicalId":54,"journal":{"name":"Organic Letters","volume":null,"pages":null},"PeriodicalIF":4.9000,"publicationDate":"2024-10-29","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Aminosulfonylation of Rhodium Carbene via Ylide Formation and 1,4-Sulfonyl Rearrangement.\",\"authors\":\"Jiahui Su, Meirong Huang, Zichun Yan, Shengbiao Tang, Xinhao Zhang, Jiangtao Sun\",\"doi\":\"10.1021/acs.orglett.4c03733\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p><p>We report here the use of pyridin-2-yl benzenesulfonates as sulfonylation reagents in a difunctionalization reaction based on oxy-pyridinium ylide chemistry, providing an effective protocol for the installation of both a sulfonyl group and a pyridone moiety into one molecule. Density functional theory (DFT) calculations disclose that the reaction process might proceed through sequential metal-bound ylide formation, keto-enol tautomerism, and the migratory rearrangement of the sulfonyl group.</p>\",\"PeriodicalId\":54,\"journal\":{\"name\":\"Organic Letters\",\"volume\":null,\"pages\":null},\"PeriodicalIF\":4.9000,\"publicationDate\":\"2024-10-29\",\"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.4c03733\",\"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.4c03733","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

我们在此报告了在基于氧-吡啶鎓酰亚胺化学的双官能化反应中使用吡啶-2-基苯磺酸盐作为磺化试剂的情况,为在一个分子中同时安装磺酰基和吡啶酮分子提供了有效的方案。密度泛函理论(DFT)计算显示,该反应过程可能是通过依次形成金属结合的醯胺、酮烯醇同分异构以及磺酰基的迁移重排进行的。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Aminosulfonylation of Rhodium Carbene via Ylide Formation and 1,4-Sulfonyl Rearrangement.

Aminosulfonylation of Rhodium Carbene via Ylide Formation and 1,4-Sulfonyl Rearrangement.

We report here the use of pyridin-2-yl benzenesulfonates as sulfonylation reagents in a difunctionalization reaction based on oxy-pyridinium ylide chemistry, providing an effective protocol for the installation of both a sulfonyl group and a pyridone moiety into one molecule. Density functional theory (DFT) calculations disclose that the reaction process might proceed through sequential metal-bound ylide formation, keto-enol tautomerism, and the migratory rearrangement of the sulfonyl group.

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.
×
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