α-Diazo-β-keto 磺酰胺的合成与反应活性

Synthesis Pub Date : 2024-08-08 DOI:10.1055/a-2348-5631
Evan R. Judge, Keith O’Shaughnessy, Simon E. Lawrence, Stuart G. Collins, Anita R. Maguire
{"title":"α-Diazo-β-keto 磺酰胺的合成与反应活性","authors":"Evan R. Judge, Keith O’Shaughnessy, Simon E. Lawrence, Stuart G. Collins, Anita R. Maguire","doi":"10.1055/a-2348-5631","DOIUrl":null,"url":null,"abstract":"<p>Copper-mediated reactions of α-diazo-β-keto sulfonamides led to a range of products, including alkynesulfonamides, enamines, and α-halosulfonamides, with no evidence for intramolecular C–H insertion in any of the reactions, in contrast to the reactivity of the comparable α-diazo-β-oxo sulfones. Use of copper(II) triflate (5 mol%) led to the isolation of a series of alkynesulfonamides (up to 12% yield) and enamines (up to 64% yield). Use of copper(II) chloride (5 mol%) led to the formation, in addition, of α-halosulfonamides; use of stoichiometric amounts of copper(II) chloride/bromide enabled facile halogenation of the β-keto sulfonamide to form α-halosulfonamides (up to 63% yield).</p> ","PeriodicalId":501298,"journal":{"name":"Synthesis","volume":"18 1","pages":""},"PeriodicalIF":0.0000,"publicationDate":"2024-08-08","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":"{\"title\":\"Synthesis and Reactivity of α-Diazo-β-keto Sulfonamides\",\"authors\":\"Evan R. Judge, Keith O’Shaughnessy, Simon E. Lawrence, Stuart G. Collins, Anita R. Maguire\",\"doi\":\"10.1055/a-2348-5631\",\"DOIUrl\":null,\"url\":null,\"abstract\":\"<p>Copper-mediated reactions of α-diazo-β-keto sulfonamides led to a range of products, including alkynesulfonamides, enamines, and α-halosulfonamides, with no evidence for intramolecular C–H insertion in any of the reactions, in contrast to the reactivity of the comparable α-diazo-β-oxo sulfones. Use of copper(II) triflate (5 mol%) led to the isolation of a series of alkynesulfonamides (up to 12% yield) and enamines (up to 64% yield). Use of copper(II) chloride (5 mol%) led to the formation, in addition, of α-halosulfonamides; use of stoichiometric amounts of copper(II) chloride/bromide enabled facile halogenation of the β-keto sulfonamide to form α-halosulfonamides (up to 63% yield).</p> \",\"PeriodicalId\":501298,\"journal\":{\"name\":\"Synthesis\",\"volume\":\"18 1\",\"pages\":\"\"},\"PeriodicalIF\":0.0000,\"publicationDate\":\"2024-08-08\",\"publicationTypes\":\"Journal Article\",\"fieldsOfStudy\":null,\"isOpenAccess\":false,\"openAccessPdf\":\"\",\"citationCount\":\"0\",\"resultStr\":null,\"platform\":\"Semanticscholar\",\"paperid\":null,\"PeriodicalName\":\"Synthesis\",\"FirstCategoryId\":\"1085\",\"ListUrlMain\":\"https://doi.org/10.1055/a-2348-5631\",\"RegionNum\":0,\"RegionCategory\":null,\"ArticlePicture\":[],\"TitleCN\":null,\"AbstractTextCN\":null,\"PMCID\":null,\"EPubDate\":\"\",\"PubModel\":\"\",\"JCR\":\"\",\"JCRName\":\"\",\"Score\":null,\"Total\":0}","platform":"Semanticscholar","paperid":null,"PeriodicalName":"Synthesis","FirstCategoryId":"1085","ListUrlMain":"https://doi.org/10.1055/a-2348-5631","RegionNum":0,"RegionCategory":null,"ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"","JCRName":"","Score":null,"Total":0}
引用次数: 0

摘要

铜介导的 α-偶氮-β-酮基磺酰胺反应产生了一系列产物,包括炔基磺酰胺、烯胺和 α-卤代磺酰胺,在任何反应中都没有证据表明分子内 C-H 插入,这与可比的 α-偶氮-β-氧代砜的反应活性形成鲜明对比。使用三酸铜(II)(5 摩尔%)可以分离出一系列炔磺酰胺(收率高达 12%)和烯胺(收率高达 64%)。使用氯化铜(II)(5 mol%)还可生成 α-卤代磺酰胺;使用等量的氯化铜/溴化物可使 β-酮基磺酰胺简单卤化,生成 α-卤代磺酰胺(收率高达 63%)。
本文章由计算机程序翻译,如有差异,请以英文原文为准。

Synthesis and Reactivity of α-Diazo-β-keto Sulfonamides

Synthesis and Reactivity of α-Diazo-β-keto Sulfonamides

Copper-mediated reactions of α-diazo-β-keto sulfonamides led to a range of products, including alkynesulfonamides, enamines, and α-halosulfonamides, with no evidence for intramolecular C–H insertion in any of the reactions, in contrast to the reactivity of the comparable α-diazo-β-oxo sulfones. Use of copper(II) triflate (5 mol%) led to the isolation of a series of alkynesulfonamides (up to 12% yield) and enamines (up to 64% yield). Use of copper(II) chloride (5 mol%) led to the formation, in addition, of α-halosulfonamides; use of stoichiometric amounts of copper(II) chloride/bromide enabled facile halogenation of the β-keto sulfonamide to form α-halosulfonamides (up to 63% yield).

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
自引率
0.00%
发文量
0
×
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