Photoredox Catalytic Defluoroalkylation of gem-Difluoroalkenes with Secondary N-Alkylanilines via C–F/C–H Coupling

IF 5 1区 化学 Q1 CHEMISTRY, ORGANIC Organic Letters Pub Date : 2024-12-22 DOI:10.1021/acs.orglett.4c04432
Haiyang Hu, Baokai Yang, Yongcan Liu, Wengang Xu, Congjian Xia, Guoqiang Xu, Mingbo Wu
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Abstract

To provide fluorinated allylamines, a visible-light photocatalytic C–F/C–H coupling of easily accessible gem-difluoroalkenes and secondary N-alkylanilines was described. The protocol proceeded under mild conditions, with excellent functional group compatibility and a broad scope including complex natural product derivatives, thus providing a green method for the preparation of high-value functionalized monofluoroalkenes. Mechanistic studies elucidated a photoredox catalyzed radical–radical coupling pathway.

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通过C-F / C-H偶联催化宝石-二氟烯烃与仲n -烷基苯胺的光氧化还原脱氟烷基化
为了获得氟化烯丙胺,描述了易获得的宝石-二氟烯烃和仲n -烷基苯胺的可见光催化C-F / C-H偶联。该方案在温和的条件下进行,具有良好的官能团相容性和广泛的范围,包括复杂的天然产物衍生物,从而为高价值功能化单氟烯烃的制备提供了绿色方法。机理研究阐明了光氧化还原催化的自由基-自由基耦合途径。
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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.
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