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通过脱羧和脱氰自由基-自由基偶联实现芳基甘氨酸与4-氰基吡啶的有机光催化吡啶化反应。

Organophotocatalytic pyridination of -arylglycines with 4-cyanopyridines by decarboxylative and decyanative radical-radical coupling.

作者信息

Pan Changduo, Xiang Chengli, Yu Jin-Tao

机构信息

School of Chemistry and Chemical Engineering, Jiangsu University of Technology, Changzhou 213001, P. R. China.

School of Petrochemical Engineering, Changzhou University, Changzhou 213164, P. R. China.

出版信息

Org Biomol Chem. 2024 Oct 2;22(38):7806-7810. doi: 10.1039/d4ob01257g.

Abstract

A photocatalytic decarboxylative aminoalkylation of 4-cyanopyridines with -arylglycines is achieved, providing 4-(aminomethyl)pyridine derivatives in moderate to good yields. This organic photocatalytic reaction undergoes a radical-radical cross-coupling process under redox-neutral conditions, featuring simple operation, readily available -arylglycines and a broad substrate scope. Mechanistic investigations indicated that a proton-coupled electron-transfer process was involved to enable the single electron transfer between the reduced photocatalyst and 4-cyanopyridine in the presence of -arylglycines.

摘要

实现了4-氰基吡啶与α-芳基甘氨酸的光催化脱羧氨基烷基化反应,以中等至良好的产率提供4-(氨基甲基)吡啶衍生物。这种有机光催化反应在氧化还原中性条件下经历自由基-自由基交叉偶联过程,具有操作简单、α-芳基甘氨酸易于获得且底物范围广的特点。机理研究表明,在α-芳基甘氨酸存在下,质子耦合电子转移过程参与其中,使还原的光催化剂与4-氰基吡啶之间能够发生单电子转移。

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