Cooperative NHC and Photoredox Catalysis for the Synthesis of 1,4-Dicarbonyl Compounds via Diacylation of Alkenes,Organic Letters

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Cooperative NHC and Photoredox Catalysis for the Synthesis of 1,4-Dicarbonyl Compounds via Diacylation of Alkenes
Organic Letters ( IF 4.9 ) Pub Date : 2022-08-03 , DOI: 10.1021/acs.orglett.2c02108
Shihao Li ₁ , Haojun Shu ₁ , Sheng Wang ₁ , Wenqing Yang ₁ , Fei Tang ₁ , Xiao-Xuan Li _{1,

2} , Shilu Fan _{1,

2} , Yi-Si Feng _{1,

2}

Affiliation

An intermolecular 1,2-diacylation of alkenes is disclosed via cooperative N-heterocyclic carbene and photoredox catalysis under the mediation of PPh₃ and Cs₂CO₃. This protocol provides a practical approach for construction of 1,4-dicarbonyl compounds toward novel diketone and pharmaceutical derivatives. Furthermore, the regioselective dicarbonyl compounds can be synthesized by adding acyl azolium salt. Mechanistic investigations suggest that the process was a critical radical/radical cross coupling of ketyl radicals with benzylic C-radicals.

中文翻译：

NHC 和光氧化还原协同催化烯烃二酰化合成 1,4-二羰基化合物

_{在PPh 3}和Cs ₂ CO ₃的介导下，通过协同的N-杂环卡宾和光氧化还原催化烯烃的分子间1,2-二酰化被公开。该协议为向新型二酮和药物衍生物构建 1,4-二羰基化合物提供了一种实用的方法。此外，区域选择性二羰基化合物可以通过添加酰基唑鎓盐来合成。机理研究表明，该过程是酮基自由基与苄基 C-自由基的关键自由基/自由基交叉偶联。

更新日期：2022-08-03

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