Photoexcited nitroarene-enabled carbon chain-elongated oxidation of alkenes via tandem oxidative cleavage and dipolar cycloaddition
Oxidation of alkenes with O<sub>3</sub> and photoexcited nitroarenes represents one of the most attractive organic chemical transformations for the synthesis of oxygen-enriched molecules. However, known achievements are mainly limited to carbon chain-shortened oxidation and carbon chain-retained oxidation of alkenes. Given that constructing higher molecular complexity is the core goal of modern synthesis, the development of chain-elongated oxidation of alkenes would be in high demand but still remains an elusive challenge so far. Herein, we report a photoexcited nitroarene-enabled highly regioselective chain-elongated oxidation of alkenes via tandem oxidative cleavage and dipolar cycloaddition, providing a broad range of synthetically-useful isoxazolidines in up to 92% yield from readily available enol ethers or styrene and derivatives under simple and mild conditions.
Authors
- Mengchun Ye (ORCID: https://orcid.org/0000-0002-2019-5365)
- Xiaoneng Cui (ORCID: https://orcid.org/0000-0001-5135-8406)
- Min Lu (ORCID: https://orcid.org/0000-0002-7818-8344)
- Weiwei Xu (ORCID: https://orcid.org/0000-0003-1047-5985)
- Qi‐Lin Zhou (ORCID: https://orcid.org/0000-0002-4700-3765)
- Xuqiang Guo
Institutions
- Nankai University (CN)
Publication Details
- Journal
- Nature Communications
- Published
- 2025-05-15
- DOI
- https://doi.org/10.1038/s41467-025-59274-4
- Citations
- 4
- Primary Topic
- Oxidative Organic Chemistry Reactions
- Type
- article
- Field-Weighted Citation Impact
- 3.74
Funders
- National Natural Science Foundation of China
- Nankai University
- Natural Science Foundation of Tianjin City
- Fundamental Research Funds for the Central Universities