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.
Authors
- Congcong Yin (ORCID: https://orcid.org/0000-0002-1533-8018)
- Di Wu (ORCID: https://orcid.org/0000-0003-1101-1170)
- Jun Jiang (ORCID: https://orcid.org/0000-0003-3401-792X)
- Kai Wang
- Xiangnan Hu
- Meilin Hu
Institutions
- China Three Gorges University (CN)
- Hubei University (CN)
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
- Field-Weighted Citation Impact
- 0.00