Photoexcited nitroarene-enabled carbon chain-elongated oxidation of alkenes via tandem oxidative cleavage and dipolar cycloaddition

Xuqiang Guo, Xinwen Cui, Mingzhen Lu, Qi-Lin Zhou, Weiwei Xu () and Mengchun Ye ()
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Xuqiang Guo: Nankai University
Xinwen Cui: Nankai University
Mingzhen Lu: Nankai University
Qi-Lin Zhou: Nankai University
Weiwei Xu: Nankai University
Mengchun Ye: Nankai University

Nature Communications, 2025, vol. 16, issue 1, 1-8

Abstract: Abstract Oxidation of alkenes with O3 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.

Date: 2025
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DOI: 10.1038/s41467-025-59274-4

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