Aerobic C(sp3)–H oxidation and oxygenation of quaternarized quinolines and pyridines by visible-light-induced photocatalysis,Organic Chemistry Frontiers

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Aerobic C(sp3)–H oxidation and oxygenation of quaternarized quinolines and pyridines by visible-light-induced photocatalysis
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2020-05-28 , DOI: 10.1039/d0qo00233j
Tonghao Han _{1,

2,

3,

4,

5} , Yunqi Jiang _{1,

2,

3,

4,

5} , Xiaochen Ji _{1,

2,

3,

4,

5} , Guo-Jun Deng _{1,

2,

3,

4,

5} , Huawen Huang _{1,

2,

3,

4,

5}

Affiliation

Herein, we report on visible-light-induced photocatalysis that enables aerobic oxidation and oxygenation of quaternarized N-heterocycles. Complete oxidation of methyl group and partial oxidation of methylene have been selectively realized. Hence, two kinds of oxygenation products (>60 new products) including carboxylate inner salts and alcohols have been accessed under mild aerobic conditions. The broad compatibility of useful functional groups in this synthetic protocol has been established. Notably, in the case of alcohol isolation recrystallization was adopted to afford high yields of products. Mechanistic studies support an oxidation process initiated by singlet oxygen for both oxygenation reactions.

中文翻译：

可见光诱导的光催化有氧C（sp3）–H氧化和季铵化喹啉和吡啶的氧化

在此，我们报道了可见光诱导的光催化作用，该反应使季铵化N杂环有氧氧化和氧合成为可能。选择性地实现了甲基的完全氧化和亚甲基的部分氧化。因此，已经在温和的好氧条件下获得了两种含氧产物（> 60种新产物），包括羧酸盐内盐和醇类。已经建立了该合成方案中有用的官能团的广泛相容性。特别地，在醇分离的情况下，采用重结晶以提供高产率的产物。机理研究支持由单线态氧引发的两个氧化反应的氧化过程。

更新日期：2020-06-30

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