NHC/光氧化还原双催化引导n -甲基自由基偶联脱羧合成α- n -芳基氨基酮

IF 4.7 1区化学 Q1 CHEMISTRY, ORGANIC

Organic Chemistry Frontiers Pub Date : 2025-07-28 DOI:10.1039/d5qo00923e

Wenying Zhao, Weikun Zeng, Shilin Zhou, Jun Zhou, Yi Jin

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引用次数: 0

摘要

在本研究中，NHC/光氧化还原系统通过稳定的n -甲基自由基中间体合成α-芳胺酮，克服了竞争性二聚化。关键的创新包括碱基介导的n -甲基自由基生成和酰基偶氮中间体引导的交叉偶联，使反应性远离寄生途径。富电子NHCs（例如，mes取代）加速酰基唑中间体的形成，在温和条件下实现广泛的底物范围。机理研究证实了自由基中间体，而衍生化则强调了生物活性分子合成的实用性。这一策略将原子经济与可扩展的阶梯经济催化相结合。

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NHC/Photoredox Dual Catalysis Directs N-methyl Radical Coupling for Decarboxylative Synthesis of α-N-Aryl amino Ketones

Herein, a synergistic NHC/photoredox system enables α-arylamino ketone synthesis via stabilized N-methyl radical intermediates, overcoming competitive dimerization. Key innovations include base-mediated N-methyl radical generation and acyl azolium intermediate-guided cross-coupling, steering reactivity away from parasitic pathways. Electron-rich NHCs (e.g., Mes-substituted) accelerating acyl azolium intermediate formation, achieving broad substrate scope under mild conditions. Mechanistic studies confirm radical intermediates, while derivatization highlights utility in bioactive molecule synthesis. This strategy merges atom economy with scalable, step-economy catalysis.

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来源期刊

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.