ortho‐Alkylation of Pyridine N‐Oxides with Alkynes by Photocatalysis: Pyridine N‐Oxide as a Redox Auxiliary,Chemistry - A European Journal

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ortho‐Alkylation of Pyridine N‐Oxides with Alkynes by Photocatalysis: Pyridine N‐Oxide as a Redox Auxiliary
Chemistry - A European Journal ( IF 3.9 ) Pub Date : 2019-04-17 , DOI: 10.1002/chem.201901065
Jonathan P. Markham ₁ , Ban Wang ₁ , Edwin D. Stevens ₁ , Stuart C. Burris ₁ , Yongming Deng ₁

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A photocatalyzed ortho‐alkylation of pyridine N‐oxide with ynamides and arylacetylenes has been developed, which yields a series of α‐(2‐pyridinyl) benzyl amides/ketones. Mechanistic studies, including electrochemical studies, radical‐trapping experiments, and Stern–Volmer fluorescence quenching studies demonstrate that pyridine N‐oxide serves as both a redox auxiliary and radical acceptor to achieve the mild photocatalytic single‐electron oxidation of carbon–carbon triple bonds with the generation of a cationic vinyl radical intermediate.

中文翻译：

吡啶N-氧化物与炔烃的邻烷基烷基化通过光催化：吡啶N-氧化物作为氧化还原助剂

已开发了使用酰胺和芳基乙炔进行光催化的吡啶N-氧化物的邻位烷基化反应，产生了一系列α-（2-吡啶基）苄基酰胺/酮。包括电化学研究，自由基捕获实验和Stern-Volmer荧光猝灭研究在内的机理研究表明，吡啶N-氧化物既可以用作氧化还原辅助剂，也可以用作自由基受体，以实现碳-碳三键的温和光催化单电子氧化阳离子乙烯基自由基中间体的产生。

更新日期：2019-04-17

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