Cross-Coupling of Benzylic and Aldehydic C–H Bonds via Photocatalytic Tandem Radical–Radical Coupling and Acceptorless Alcohol Dehydrogenation,The Journal of Organic Chemistry

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Cross-Coupling of Benzylic and Aldehydic C–H Bonds via Photocatalytic Tandem Radical–Radical Coupling and Acceptorless Alcohol Dehydrogenation
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2024-01-16 , DOI: 10.1021/acs.joc.3c02427
Yunfei Guo ₁ , Jipeng Qi ₁ , Hongyu Guo ₁ , Rongfang Liu ₂ , Rong Zhou _{1,

3}

Affiliation

The construction of a C–C bond by cross-coupling of two different C–H bonds with the release of hydrogen gas represents an ideal yet challenging bond formation strategy. Herein, we report a photocatalytic metal-free cross-coupling of benzylic and aldehydic C–H bonds by synergistic catalysis of organophotocatalyst 4CzIPN and a thiol, which affords the corresponding α-aryl ketones in acceptable yields along with hydrogen evolution. The mechanistic investigation indicates a radical–radical coupling to give an intermediary alcohol, followed by an acceptorless alcohol dehydrogenation.

中文翻译：

通过光催化串联自由基-自由基偶联和无受体醇脱氢实现苄基和醛基 C-H 键的交叉偶联

通过两个不同的 C-H 键交叉偶联并释放氢气来构建 C-C 键代表了一种理想但具有挑战性的键形成策略。在此，我们报道了通过有机光催化剂4CzIPN和硫醇的协同催化，实现了苄基和醛基C-H键的光催化无金属交叉偶联，这以可接受的产率提供了相应的α-芳基酮，同时析出氢气。机理研究表明自由基-自由基偶联产生中间醇，然后进行无受体醇脱氢。

更新日期：2024-01-16

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