Photoexcited nitroarene-enabled carbon chain-elongated oxidation of alkenes via tandem oxidative cleavage and dipolar cycloaddition.
basic_science · Level V
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- Record sourced from PubMed, PMID 40374615.
- Also identified by DOI 10.1038/s41467-025-59274-4 and PMC identifier 12081768.
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Abstract
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.