ArticleChemical science2023
Oxidative cleavage of ketoximes to ketones using photoexcited nitroarenes.
Article in Chemical science, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 8 papers.
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Who cites it
8 citing papers in PubMed.
- Article
- Skeletal Editing of Alkenes with Nitroarenes via Photoinduced Rearrangement of N─O═C Dipoles Forms Lactams and Amides.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2026Article
- Photoinduced Cleavage of Alkenyl Fluorides for Nucleophilic Acyl Substitution via In Situ Generated Acyl Fluorides.Organic letters · 2025Article
- Photochromic Oxime Directing Groups for Spatially Controlled Pd-Catalyzed C-H Difunctionalization with Tandem Electrophiles.ACS catalysis · 2025Article
- Total Synthesis of the Nominal Structure of (+)-Talaromyolide D.Journal of the American Chemical Society · 2025Article
- Photoexcited nitroarene-enabled carbon chain-elongated oxidation of alkenes via tandem oxidative cleavage and dipolar cycloaddition.Nature communications · 2025Article
- Merging Photoexcited Nitroarenes with Lewis Acid Catalysis for the Anti-Markovnikov Oxidation of Alkenes.Organic letters · 2025Article
- Recent Advances in Photoinduced Oxidative Cleavage of Alkenes.Synthesis · 2024Article
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
The methoxime group has emerged as a versatile directing group for a variety of C-H functionalizations. Despite its importance as a powerful functional handle, conversion of methoximes to the parent ketone, which is often desired, usually requires harsh and functional group intolerant reaction conditions. Therefore, the application of methoximes and their subsequent conversion to the corresponding ketone in a late-stage context can be problematic. Here, we present an alternative set of conditions to achieve mild and functional group tolerant conversion of methoximes to the parent ketones using photoexcited nitroarenes. The utility of this methodology is showcased in its application in the total synthesis of cephanolide D. Furthermore, mechanistic insight into this transformation obtained using isotope labeling studies as well as the analysis of reaction byproducts is provided.
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Registered trials
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