2022
DOI: 10.1021/jacs.2c05648
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Photoinduced Oxygen Transfer Using Nitroarenes for the Anaerobic Cleavage of Alkenes

Abstract: Herein we report the anaerobic cleavage of alkenes into carbonyl compounds using nitroarenes as oxygen transfer reagents under visible light. This approach serves as a safe and practical alternative to mainstream oxidative cleavage protocols, such as ozonolysis and the Lemieux−Johnson reaction. A wide range of alkenes possessing oxidatively sensitive functionalities underwent anaerobic cleavage to generate carbonyl derivatives with high efficiency and regioselectivity. Mechanistic studies support that the tran… Show more

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Cited by 74 publications
(63 citation statements)
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“…Based on the above mechanistic experiments and previous reports, 19,20,34 the plausible mechanisms were proposed (Scheme 7). If ground-state nitroarene ( 1a ) is exposed to appropriate irradiation, it could be photoexcited to the long-lived triplet state (T), which has a biradical character.…”
Section: Resultsmentioning
confidence: 77%
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“…Based on the above mechanistic experiments and previous reports, 19,20,34 the plausible mechanisms were proposed (Scheme 7). If ground-state nitroarene ( 1a ) is exposed to appropriate irradiation, it could be photoexcited to the long-lived triplet state (T), which has a biradical character.…”
Section: Resultsmentioning
confidence: 77%
“…According to the previous reports concerning the reduction of nitroarenes to nitroso compounds, 19,19 a ,20 we assume that nitroso and carbonyl might be the outcomes of the d -HAA process. Therefore, we designed the less fast intermolecular HAA reaction to verify this hypothesis and try to detect the active nitroso species.…”
Section: Resultsmentioning
confidence: 99%
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“…The recent independent reports by the research groups of Parasram and Leonori have now addressed this longstanding problem by exploring the excited state reactivities of nitroarenes with alkenes under mild purple light photosensitization conditions. [9,10] Unlike powerful mercury lamps, mild photosensitization conditions allowed formation of the "N-doped" ozonide and a controlled cleavage of the alkenyl CÀ C bond to generate the corresponding carbonyl compounds in high yields (Scheme 2C). Parasram and co-workers identified 4-cyanonitrobenzene as an effective one step oxygen transfer agent for styrenes at room temperature.…”
mentioning
confidence: 99%