ArticleAngewandte Chemie (International ed. in English)2023
Wacker Oxidation of Methylenecyclobutanes: Scope and Selectivity in an Unusual Setting.
Article in Angewandte Chemie (International ed. in English), 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 10 papers.
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Who cites it
10 citing papers in PubMed.
- Article
- Advances in Ligand Development for Wacker-Type Oxidation.ACS omega · 2026Review
- Nickel-catalyzed ring-opening difunctionalization of methylenecyclobutanes via strain-release-enabled C-C activation.Nature communications · 2026Article
- Visible-Light-Induced Bond Homolysis in Titanacyclopentadienes for the Catalytic Cyclodimerization of Internal Alkynes.Journal of the American Chemical Society · 2025Article
- Wacker Oxidation of Trisubstituted Alkenes: Pd(II)-Catalyzed Oxidative Ring Expansion of Exocyclic α,β-Unsaturated Carbonyl to 2-Fluoro-1,3-Dicarbonyl Compounds.Angewandte Chemie (International ed. in English) · 2025Article
- Synthesis of Benzo-Fused Cycloheptanones from Cyclobutanol Derivatives by a C-C Cleavage/Cross-Coupling/Enolate Arylation Sequence.Synthesis · 2025Article
- Asymmetric Migratory Tsuji-Wacker Oxidation Enables the Enantioselective Synthesis of Hetero- and Isosteric Diarylmethanes.Journal of the American Chemical Society · 2024Article
- Covalent bidentate ligand-enabled regioselective Wacker-type oxidation of olefins.RSC advances · 2024Article
- Immobilization of Trifluoromethyl-Substituted Pyridine-Oxazoline Ligand and Its Application in Asymmetric Continuous Flow Synthesis of Benzosultams.The Journal of organic chemistry · 2023Article
- Wacker Oxidation of Methylenecyclobutanes: Scope and Selectivity in an Unusual Setting.Angewandte Chemie (International ed. in English) · 2023Article
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Authors and funding
3 authors.
Funding
Abstract
Methylenecyclobutanes are found to undergo Wacker oxidation via a semi-pinacol-type rearrangement. Key to a successful process is the use of tert-butyl nitrite as oxidant, which not only enables efficient catalyst turn-over but also ensures high Markovnikov-selectivity under mild conditions. Thus, cyclopentanones (26 examples) can be accessed in an overall good yield and excellent selectivity (up to 97 % yield, generally >99 : 1 ketone:aldehyde ratio). Stereochemical analysis of the reaction sequence reveals migration aptitudes in line with related 1,2-shifts. By introducing a pyox ligand to palladium, prochiral methylenecyclobutanes can be desymmetrized, thus realizing the first enantioselective Wacker oxidation.
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