Blue Light-Induced Formal Insertion Reaction of α-Siloxy Carbene into C-H Bond of 1,3-Diketones

doi:10.6023/cjoc202405026

Chinese Journal of Organic Chemistry

ARTICLE

蓝光诱导的α-硅氧基卡宾与1,3-二酮C-H键的形式上插入反应

蒋馨雨^a, 张新科^a, 方曦^a, 徐新芳^b,*

^a中山大学药学院广东省广州市 510006;
^b浙江理工大学化学与化工学院浙江省杭州市 310018

收稿日期:2024-05-17 修回日期:2024-06-30
基金资助:
国家自然科学基金(No. 22371309)资助项目.

Blue Light-Induced Formal Insertion Reaction of α-Siloxy Carbene into C-H Bond of 1,3-Diketones

Jiang Xinyu^a, Zhang Xinke^a, Fang Xi^a, Xu Xinfang^b,*

^aSchool of Pharmaceutical Sciences, Sun Yat-sen University, Guangzhou, 510006;
^bSchool of Chemistry and Chemical Engineering, Zhejiang Sci-Tech University, Hangzhou, 310018

Received:2024-05-17 Revised:2024-06-30
Contact: *E-mail: xuxinfang@zstu.edu.cn
Supported by:
National Natural Science Foundation of China (No. 22371309)

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Abstract

A blue light-induced formal insertion reaction of α-siloxy carbene into the C-H bond of 1,3-diketones has been reported. Under the irradiation of blue light, acylsilane converted to α-siloxy carbene, which then undergoes formal C-H bond insertion reaction with the enol form of 1,3-diketone. This method using readily available and relative stable acylsilane as carbene precursor, which features a simple and metal-free approach under mild conditions. Moreover, the synthetic potential of this protocol has been demonstrated by performing the reaction on a gram scale with comparable high yield.

Key words: photoinduced, α-siloxy carbene, 1,3-diketone, C-H bond insertion reaction

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Jiang Xinyu, Zhang Xinke, Fang Xi, Xu Xinfang. Blue Light-Induced Formal Insertion Reaction of α-Siloxy Carbene into C-H Bond of 1,3-Diketones[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202405026.

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蓝光诱导的α-硅氧基卡宾与1,3-二酮C-H键的形式上插入反应

Blue Light-Induced Formal Insertion Reaction of α-Siloxy Carbene into C-H Bond of 1,3-Diketones

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