Access to All-Carbon Quaternary Centers by Photocatalytic Fluoroalkylation of α-Halo Carbonyl Compounds,Organic Letters

当前位置： X-MOL 学术 › Org. Lett. › 论文详情

Our official English website, www.x-mol.net, welcomes your feedback! (Note: you will need to create a separate account there.)

Access to All-Carbon Quaternary Centers by Photocatalytic Fluoroalkylation of α-Halo Carbonyl Compounds
Organic Letters ( IF 4.9 ) Pub Date : 2024-02-27 , DOI: 10.1021/acs.orglett.4c00041
Gang Liu _{1,

2} , Haigen Shen _{2,

3} , Zhaobin Wang _{2,

3}

Affiliation

Perfluoroalkyl groups have become significantly important in pharmaceutical and agrochemical applications. In this study, we present a visible light-mediated photoredox neutral strategy for the fluoroalkylation of tertiary alkyl chlorides under transition-metal-free conditions. This method allows for the facile synthesis of fluoroalkylated all-carbon quaternary centers, exhibiting excellent functional group compatibility. Mechanistic studies reveal the involvement of two reactive radical intermediates and the in situ formation of metal enolates in a radical-polar crossover manner. The versatility of this methodology is demonstrated through synthetic transformations based on the carbonyl group, showcasing its potential for the rapid assembly of diverse organic molecules bearing fluoroalkyl all-carbon quaternary centers.

中文翻译：

通过 α-卤代羰基化合物的光催化氟烷基化获得全碳四元中心

全氟烷基在医药和农用化学品应用中变得非常重要。在这项研究中，我们提出了一种可见光介导的光氧化还原中性策略，用于在无过渡金属的条件下进行叔烷基氯的氟烷基化。该方法可以轻松合成氟烷基化的全碳四元中心，并表现出优异的官能团相容性。机理研究揭示了两种反应性自由基中间体的参与以及以自由基-极性交叉方式原位形成金属烯醇化物。该方法的多功能性通过基于羰基的合成转化得到证明，展示了其快速组装带有氟烷基全碳四元中心的多种有机分子的潜力。

更新日期：2024-02-27

点击分享查看原文

点击收藏

阅读更多本刊新发论文本刊介绍/投稿指南