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

Guo, Xuqiang; Cui, Xinwen; Lu, Mingzhen; Zhou, Qi-Lin; Xu, Weiwei; Ye, Mengchun · Nat Commun · 2025

basic_science · Level V

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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.