Phosphorothiolation of Benzylic C(sp <sup>3</sup> )–H via EnT-Mediated Radical–Radical Cross-Coupling

Direct phosphorothiolation of benzylic C(sp<sup>3</sup>)-H bonds remains underexplored. Herein, we report an energy transfer (EnT)-mediated method that achieves this via controlled radical-radical cross-coupling, using inexpensive K<sub>2</sub>S<sub>2</sub>O<sub>8</sub> as both an oxidant and a hydrogen atom transfer (HAT) reagent. This strategy eliminates prefunctionalization steps, demonstrates excellent chemoselectivity, and provides an atom- and step-economical route to diverse alkyl phosphorothioate compounds.

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Publication Details

Journal
Organic Letters
Published
2025-12-24
DOI
https://doi.org/10.1021/acs.orglett.5c04989
Citations
1
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.94
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article

Phosphorothiolation of Benzylic C(sp 3 )–H via EnT-Mediated Radical–Radical Cross-Coupling

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1 citations
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Radical Photochemical Reactions
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article

Phosphorothiolation of Benzylic C(sp 3 )–H via EnT-Mediated Radical–Radical Cross-Coupling

Longyu Wang, Xinyi Guo, Yan Gao, Mengke Yang, Pengbo Zhang
article en
1 citations

Abstract

Direct phosphorothiolation of benzylic C(sp<sup>3</sup>)-H bonds remains underexplored. Herein, we report an energy transfer (EnT)-mediated method that achieves this via controlled radical-radical cross-coupling, using inexpensive K<sub>2</sub>S<sub>2</sub>O<sub>8</sub> as both an oxidant and a hydrogen atom transfer (HAT) reagent. This strategy eliminates prefunctionalization steps, demonstrates excellent chemoselectivity, and provides an atom- and step-economical route to diverse alkyl phosphorothioate compounds.

Organic LettersVol. 28(1)
Chinese Academy of Sciences (CN), Fujian Institute of Research on the Structure of Matter (CN)
Affordable and clean energy
Openalex Percentile: Top 19%
Radical Photochemical Reactions
0.94
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