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通过光催化后期官能团化方案获得SCF取代的中氮茚。

Access to SCF-Substituted Indolizines via a Photocatalytic Late-Stage Functionalization Protocol.

作者信息

Stefanoni Kevin Klaus, Wilhelm René

机构信息

Institute of Organic Chemistry, Clausthal University of Technology, Leibnizstr. 6, 38678 Clausthal-Zellerfeld, Germany.

出版信息

Org Lett. 2025 Aug 8;27(31):8389-8393. doi: 10.1021/acs.orglett.5c02079. Epub 2025 Jul 21.

DOI:10.1021/acs.orglett.5c02079
PMID:40685993
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12340967/
Abstract

A mild, scalable, and highly chemoselective photocatalytic method was developed for direct indolizine functionalization with -((trifluoromethyl)thio)saccharin, yielding high amounts of desired products while tolerating various functional groups. The photoredox catalyst employed offers a straightforward and inexpensive alternative to commercially available catalysts. Additionally, a 3-SCF analogue of a histamine H3 receptor antagonist was synthesized with excellent yield, demonstrating the strategy's potential in developing biologically relevant molecules.

摘要

开发了一种温和、可扩展且具有高度化学选择性的光催化方法,用于用-((三氟甲基)硫代)糖精直接对中氮茚进行官能化,在容忍各种官能团的同时产生大量所需产物。所使用的光氧化还原催化剂为市售催化剂提供了一种直接且廉价的替代方案。此外,以优异的产率合成了一种组胺H3受体拮抗剂的3-SCF类似物,证明了该策略在开发具有生物学相关性的分子方面的潜力。

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本文引用的文献

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Bichromophoric Ruthenium Complexes for Photocatalyzed Late-Stage Synthesis of Trifluoromethylated Indolizines.用于光催化后期合成三氟甲基化中氮茚的双色钌配合物
J Org Chem. 2025 May 16;90(19):6491-6503. doi: 10.1021/acs.joc.5c00319. Epub 2025 May 5.
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Trifluoromethylthiolation of Tryptophan and Tyrosine Derivatives: A Tool for Enhancing the Local Hydrophobicity of Peptides.色氨酸和酪氨酸衍生物的三氟甲基化:增强肽局部疏水性的工具。
J Org Chem. 2023 Sep 15;88(18):13169-13177. doi: 10.1021/acs.joc.3c01373. Epub 2023 Sep 6.
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Diquat Based Dyes: A New Class of Photoredox Catalysts and Their Use in Aerobic Thiocyanation.
二氯二吡啶基阳离子类染料:一类新型光氧化还原催化剂及其在有氧条件下的硫氰化反应中的应用。
Chemistry. 2023 Apr 18;29(22):e202203541. doi: 10.1002/chem.202203541. Epub 2023 Mar 8.
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Combinatorial Anticancer Drug Screen Identifies Off-Target Effects of Epigenetic Chemical Probes.组合式抗癌药物筛选鉴定出表观遗传化学探针的脱靶效应。
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Decatungstate Catalyzed Synthesis of Trifluoromethylthioesters from Aldehydes via a Radical Process.Decatungstate 催化醛通过自由基过程合成三氟甲硫基酯。
J Org Chem. 2022 Jan 7;87(1):765-775. doi: 10.1021/acs.joc.1c02244. Epub 2021 Dec 9.
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Recent advances in the synthesis of indolizine and its derivatives by radical cyclization/cross-coupling.通过自由基环化/交叉偶联合成吲哚嗪及其衍生物的最新进展。
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