Visible-Light-Catalyzed Phosphorylation of Alkenes Enabled by Oxime Ether Reagents

Existing photocatalytic alkene phosphorylation relies on oxime ester-based phosphorus radical precursors, while conventional oxime ethers are severely limited by their inert N-O bond cleavage under photochemical conditions, restricting their synthetic utility. To overcome this bottleneck, we rationally designed and synthesized a novel class of photocleavable oxime ether phosphorylating reagents by incorporating a labile C-Br bond as an exogenous radical initiation site. This tailored molecular design successfully circumvents the intrinsic photoinertness of classic oxime ethers and enables efficient visible-light-driven generation of key phosphoryl radicals. The mild protocol affords structurally diversified alkenyl phosphates with broad substrate tolerance, scalable synthetic capability, and excellent functional group compatibility. This work establishes a distinctive radical phosphorylation strategy and greatly expands the applicability of oxime ether scaffolds in photoredox catalysis and organophosphorus synthesis.

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Publication Details

Journal
The Journal of Organic Chemistry
Published
2026-11-11
DOI
https://doi.org/10.1021/acs.joc.6c02212
Primary Topic
Radical Photochemical Reactions
Type
article
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article

Visible-Light-Catalyzed Phosphorylation of Alkenes Enabled by Oxime Ether Reagents

Congcong Yin, Di Wu, Jun Jiang, Kai Wang et al.
The Journal of Organic Chemistry
Radical Photochemical Reactions
article

Visible-Light-Catalyzed Phosphorylation of Alkenes Enabled by Oxime Ether Reagents

Congcong Yin, Di Wu, Jun Jiang, Kai Wang, Xiangnan Hu, Meilin Hu
article en

Abstract

Existing photocatalytic alkene phosphorylation relies on oxime ester-based phosphorus radical precursors, while conventional oxime ethers are severely limited by their inert N-O bond cleavage under photochemical conditions, restricting their synthetic utility. To overcome this bottleneck, we rationally designed and synthesized a novel class of photocleavable oxime ether phosphorylating reagents by incorporating a labile C-Br bond as an exogenous radical initiation site. This tailored molecular design successfully circumvents the intrinsic photoinertness of classic oxime ethers and enables efficient visible-light-driven generation of key phosphoryl radicals. The mild protocol affords structurally diversified alkenyl phosphates with broad substrate tolerance, scalable synthetic capability, and excellent functional group compatibility. This work establishes a distinctive radical phosphorylation strategy and greatly expands the applicability of oxime ether scaffolds in photoredox catalysis and organophosphorus synthesis.

The Journal of Organic Chemistry
China Three Gorges University (CN), Hubei University (CN)
Radical Photochemical Reactions
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