Photogeneration of β-Borylsilyl Radical via Decarboxylation of <i>N</i>-Hydroxyphthalimide Esters

<i>Gem</i>-borylsilylalkanes are versatile intermediates in organic synthesis, and the traditional synthesis methods have mainly focused on metal reagents, the insertion reactions of diazo compounds, and hydrosilylation/hydroborylation reactions of unsaturated bonds. Herein, a novel, efficient <i>gem</i>-borylsilylalkanes synthesis via a radical approach is reported. This method introduced a β-<i>gem</i>-borylsilyl NHPI ester as the precursor of the β-borylsilyl radical that, coupling with radical acceptors under photo conditions, and the corresponding <i>gem</i>-borylsilylalkanes bearing unsaturated bonds, facilitate subsequent transformations.

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Publication Details

Journal
Organic Letters
Published
2024-10-16
DOI
https://doi.org/10.1021/acs.orglett.4c03393
Citations
3
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.75

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article

Photogeneration of β-Borylsilyl Radical via Decarboxylation of N-Hydroxyphthalimide Esters

Guotao Lin, Jian Xu, Qingqing Xuan, Qiuling Song et al.
3 citations
Organic Letters
Radical Photochemical Reactions
0.75
article

Photogeneration of β-Borylsilyl Radical via Decarboxylation of N-Hydroxyphthalimide Esters

Guotao Lin, Jian Xu, Qingqing Xuan, Qiuling Song, Yu Guo, Mengjie Zhang
article en
3 citations

Abstract

<i>Gem</i>-borylsilylalkanes are versatile intermediates in organic synthesis, and the traditional synthesis methods have mainly focused on metal reagents, the insertion reactions of diazo compounds, and hydrosilylation/hydroborylation reactions of unsaturated bonds. Herein, a novel, efficient <i>gem</i>-borylsilylalkanes synthesis via a radical approach is reported. This method introduced a β-<i>gem</i>-borylsilyl NHPI ester as the precursor of the β-borylsilyl radical that, coupling with radical acceptors under photo conditions, and the corresponding <i>gem</i>-borylsilylalkanes bearing unsaturated bonds, facilitate subsequent transformations.

Organic LettersVol. 26(42)
Huaqiao University (CN), Henan Normal University (CN), Fuzhou University (CN)
Henan Normal University, National Natural Science Foundation of China, Natural Science Foundation of Fujian Province
Clean water and sanitation
Openalex Percentile: Top 32%
Radical Photochemical Reactions
0.75
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