Visible-light-induced dehydrogenative β-trifluoromethylthiolation of tertiary amines and direct β-trifluoromethylthiolation of enamides†

IF 4.6 1区 化学 Q1 CHEMISTRY, ORGANIC
Yaqi Song, Zhongling Jiang, Yi Zhu, Tian-Yu Sun, Xiao-Feng Xia and Dawei Wang
{"title":"Visible-light-induced dehydrogenative β-trifluoromethylthiolation of tertiary amines and direct β-trifluoromethylthiolation of enamides†","authors":"Yaqi Song, Zhongling Jiang, Yi Zhu, Tian-Yu Sun, Xiao-Feng Xia and Dawei Wang","doi":"10.1039/D3QO01231J","DOIUrl":null,"url":null,"abstract":"<p >Facilitated by electron donor–acceptor complexes, an efficient dehydrogenative β-trifluoromethylthiolation of tertiary amines with <em>N</em>-trifluoromethylthiophthalimide is presented under transition-metal-free, external oxidant-free, photocatalyst-free and mild reaction conditions. This protocol accommodates a range of substituted piperidines, as well as seven- and eight-membered saturated heterocycles. Additionally, employing this photocatalyst-free approach, direct β-trifluoromethylthiolation of electron-rich enamides was also achieved through the involvement of a photoactive electron donor–acceptor (EDA) complex.</p>","PeriodicalId":97,"journal":{"name":"Organic Chemistry Frontiers","volume":" 20","pages":" 5284-5290"},"PeriodicalIF":4.6000,"publicationDate":"2023-09-14","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Organic Chemistry Frontiers","FirstCategoryId":"92","ListUrlMain":"https://pubs.rsc.org/en/content/articlelanding/2023/qo/d3qo01231j","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

Abstract

Facilitated by electron donor–acceptor complexes, an efficient dehydrogenative β-trifluoromethylthiolation of tertiary amines with N-trifluoromethylthiophthalimide is presented under transition-metal-free, external oxidant-free, photocatalyst-free and mild reaction conditions. This protocol accommodates a range of substituted piperidines, as well as seven- and eight-membered saturated heterocycles. Additionally, employing this photocatalyst-free approach, direct β-trifluoromethylthiolation of electron-rich enamides was also achieved through the involvement of a photoactive electron donor–acceptor (EDA) complex.

Abstract Image

可见光诱导叔胺的脱氢β-三氟甲硫基化和烯酰胺的直接β-三氟甲硫基化度†
在电子供体-受体配合物的促进下,在无过渡金属、无外部氧化剂、无光催化剂和温和的反应条件下,叔胺与N-三氟甲硫基邻苯二甲酰亚胺发生了高效的脱氢β-三氟甲硫基化反应。该方案适用于一系列取代的哌啶,以及七元和八元饱和杂环。此外,采用这种无光催化剂的方法,还通过光活性电子供体-受体(EDA)复合物实现了富电子烯酰胺的直接β-三氟甲硫基化。
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
Organic Chemistry Frontiers
Organic Chemistry Frontiers CHEMISTRY, ORGANIC-
CiteScore
7.90
自引率
11.10%
发文量
686
审稿时长
1 months
期刊介绍: Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.
×
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