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可见光诱导的3,4-二氢喹喔啉-2(1)-酮与二苯基氧化膦的无金属和光敏剂的C(sp)-H磷酸化反应

Visible-Light-Induced Metal- and Photosensitizer-Free C(sp)-H Phosphorylation of 3,4-Dihydroquinoxalin-2(1)-ones with Diphenylphosphine Oxide.

作者信息

Jia Li, Lu Yanan, Chen Ying, Zhong Yu, Zhao Fen, Zhou Yongyun

机构信息

Yunnan Key Laboratory of Chiral Functional Substance Research and Application, Yunnan Minzu University, Kunming, Yunnan 650500, China.

Department School of Chemistry and Environment, Yunnan Minzu University, Kunming, Yunnan 650500, China.

出版信息

J Org Chem. 2024 Aug 16;89(16):11659-11664. doi: 10.1021/acs.joc.4c01376. Epub 2024 Aug 1.

Abstract

Herein, we report a direct phosphorylation of the C(sp)-H bond of 3,4-dihydroquinoxalin-2(1)-ones using oxygen as a green oxidant under visible light at room temperature. This transformation was readily accomplished in the absence of metal and photosensitizer to construct new C(sp)-P bonds and provide a series of phosphonylated dihydroquinoxalin-2-ones in good to excellent yields. This approach opens straightforward and environmentally friendly access to 3-phosphoryl quinoxalin-2-ones derivatives.

摘要

在此,我们报道了在室温可见光下,以氧气作为绿色氧化剂,对3,4-二氢喹喔啉-2(1)-酮的C(sp)-H键进行直接磷酸化反应。该转化在无金属和光敏剂的情况下即可轻松完成,用于构建新的C(sp)-P键,并以良好至优异的产率提供一系列膦酰化二氢喹喔啉-2-酮。这种方法为3-磷酰基喹喔啉-2-酮衍生物提供了直接且环境友好的合成途径。

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