C-H Trifluoromethylthiolation of aldehyde hydrazones.

IF 2.2 4区 化学 Q2 CHEMISTRY, ORGANIC
Beilstein Journal of Organic Chemistry Pub Date : 2024-11-12 eCollection Date: 2024-01-01 DOI:10.3762/bjoc.20.242
Victor Levet, Balu Ramesh, Congyang Wang, Tatiana Besset
{"title":"C-H Trifluoromethylthiolation of aldehyde hydrazones.","authors":"Victor Levet, Balu Ramesh, Congyang Wang, Tatiana Besset","doi":"10.3762/bjoc.20.242","DOIUrl":null,"url":null,"abstract":"<p><p>The selective C-H trifluoromethylthiolation of aldehyde hydrazones afforded interesting fluorinated building blocks, which could be used as a synthetic platform. Starting from readily available (hetero)aromatic and aliphatic hydrazones, the formation of a C-SCF<sub>3</sub> bond was achieved under oxidative and mild reaction conditions in the presence of the readily available AgSCF<sub>3</sub> salt via a one-pot sequential process (28 examples, up to 91% yield). Mechanistic investigations revealed that AgSCF<sub>3</sub> was the active species in the transformation.</p>","PeriodicalId":8756,"journal":{"name":"Beilstein Journal of Organic Chemistry","volume":"20 ","pages":"2883-2890"},"PeriodicalIF":2.2000,"publicationDate":"2024-11-12","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"https://www.ncbi.nlm.nih.gov/pmc/articles/PMC11571951/pdf/","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Beilstein Journal of Organic Chemistry","FirstCategoryId":"92","ListUrlMain":"https://doi.org/10.3762/bjoc.20.242","RegionNum":4,"RegionCategory":"化学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"2024/1/1 0:00:00","PubModel":"eCollection","JCR":"Q2","JCRName":"CHEMISTRY, ORGANIC","Score":null,"Total":0}
引用次数: 0

Abstract

The selective C-H trifluoromethylthiolation of aldehyde hydrazones afforded interesting fluorinated building blocks, which could be used as a synthetic platform. Starting from readily available (hetero)aromatic and aliphatic hydrazones, the formation of a C-SCF3 bond was achieved under oxidative and mild reaction conditions in the presence of the readily available AgSCF3 salt via a one-pot sequential process (28 examples, up to 91% yield). Mechanistic investigations revealed that AgSCF3 was the active species in the transformation.

醛肼的 C-H 三氟甲基硫代反应。
醛肼的选择性 C-H 三氟甲基硫代反应产生了有趣的含氟构筑基块,可用作合成平台。从现成的(杂)芳香族和脂肪族酰肼开始,在氧化和温和的反应条件下,在现成的 AgSCF3 盐存在下,通过一锅顺序过程实现了 C-SCF3 键的形成(28 个实例,收率高达 91%)。机理研究表明,AgSCF3 是转化过程中的活性物种。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 求助全文
来源期刊
CiteScore
4.90
自引率
3.70%
发文量
167
审稿时长
1.4 months
期刊介绍: The Beilstein Journal of Organic Chemistry is an international, peer-reviewed, Open Access journal. It provides a unique platform for rapid publication without any charges (free for author and reader) – Platinum Open Access. The content is freely accessible 365 days a year to any user worldwide. Articles are available online immediately upon publication and are publicly archived in all major repositories. In addition, it provides a platform for publishing thematic issues (theme-based collections of articles) on topical issues in organic chemistry. The journal publishes high quality research and reviews in all areas of organic chemistry, including organic synthesis, organic reactions, natural product chemistry, structural investigations, supramolecular chemistry and chemical biology.
×
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