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光氧化还原/铜双催化通过自由基-极性交叉的苄基 C-H 酯化反应。

Photoredox/Copper Dual-Catalyzed Benzylic C-H Esterification via Radical-Polar Crossover.

机构信息

College of Medicine, Jiaxing University, 118 Jiahang Road, Jiaxing 314001, P. R. China.

Jiangsu Key Laboratory of Neuropsychiatric Diseases and College of Pharmaceutical Sciences, Soochow University, 199 Ren'ai Road, Suzhou, Jiangsu 215123, P. R. China.

出版信息

Org Lett. 2022 Apr 15;24(14):2679-2683. doi: 10.1021/acs.orglett.2c00763. Epub 2022 Mar 31.

Abstract

Herein, we report a distinctive photoredox/copper dual-catalyzed esterification of benzylic C-H bonds through the combination of photoredox-mediated hydrogen atom transfer and Cu(II)-mediated radical-polar crossover. This methodology demonstrates a high functional group tolerance (>40 examples) and moderate to good yields with structurally diverse benzylic C-H substrates. Notably, stoichiometric amounts of carboxylic acids are used as coupling partners, which allows the synthesis of structurally diverse benzylic esters and the late-stage functionalization of pharmaceuticals.

摘要

在此,我们报告了一种独特的光氧化还原/铜双催化苄基 C-H 键酯化反应,通过光氧化还原介导的氢原子转移和 Cu(II)介导的自由基-极性交叉的结合。该方法表现出高的官能团容忍性(>40 个实例)和中等至良好的产率,具有结构多样的苄基 C-H 底物。值得注意的是,使用化学计量量的羧酸作为偶联伙伴,这允许合成结构多样的苄基酯和药物的后期功能化。

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