ArticleJournal of the American Chemical Society2014
N-Boc amines to oxazolidinones via Pd(II)/bis-sulfoxide/Brønsted acid co-catalyzed allylic C-H oxidation.
Article in Journal of the American Chemical Society, 2014. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed, 98 citations in OpenAlex.
- Chiral Anthranyl Bis-sulfoxides with Modular Chiroptical Properties Controlled by an Ionic Stimulus.ACS omega · 2026Article
- C(spJournal of the American Chemical Society · 2025Article
- Stereoselective Synthesis of ChiralThe Journal of organic chemistry · 2024Article
- Palladium-catalyzed cross-coupling of alcohols with olefins by positional tuning of a counteranion.Science (New York, N.Y.) · 2024Article
- General Regio- and Diastereoselective Allylic C-H Oxygenation of Internal Alkenes.Journal of the American Chemical Society · 2024Article
- Palladium/Norbornene-Catalyzed Direct Vicinal Di-Carbo-Functionalization of Indoles: Reaction Development and Mechanistic Study.Angewandte Chemie (International ed. in English) · 2023Article
- Diastereoconvergent synthesis ofChemical science · 2022Article
- Allylic C-H amination cross-coupling furnishes tertiary amines by electrophilic metal catalysis.Science (New York, N.Y.) · 2022Article
- Regiocontrol in the oxidative Heck reaction of indole by ligand-enabled switch of the regioselectivity-determining step.Chemical science · 2020Article
- Synthesis of Functionalized Indoles via Palladium-Catalyzed Cyclization ofMolecules (Basel, Switzerland) · 2020Article
- Iridium-Catalyzed, β-Selective C(spJournal of the American Chemical Society · 2018Article
- Diastereoselective C-H carbonylative annulation of aliphatic amines: a rapid route to functionalized γ-lactams.Chemical science · 2018Article
- Arylative Intramolecular Allylation of Ketones with 1,3-Enynes Enabled by Catalytic Alkenyl-to-Allyl 1,4-Rhodium(I) Migration.Angewandte Chemie (International ed. in English) · 2017Article
- Review
- Iron-Catalyzed Oxyfunctionalization of Aliphatic Amines at Remote Benzylic C-H Sites.Organic letters · 2016Article
- Enantioselective Allylic C-H Oxidation of Terminal Olefins to Isochromans by Palladium(II)/Chiral Sulfoxide Catalysis.Angewandte Chemie (International ed. in English) · 2016Article
- Collaborative Total Synthesis: Routes to (±)-Hippolachnin A Enabled by Quadricyclane Cycloaddition and Late-Stage C-H Oxidation.Journal of the American Chemical Society · 2016Article
- Aerobic Linear Allylic C-H Amination: Overcoming Benzoquinone Inhibition.Journal of the American Chemical Society · 2016Article
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Authors and funding
2 authors at 1 institution in 1 country.
Funding
Abstract
A Pd(II)/bis-sulfoxide/Brønsted acid catalyzed allylic C-H oxidation reaction for the synthesis of oxazolidinones from simple N-Boc amines is reported. A range of oxazolidinones are furnished in good yields (avg 63%) and excellent diastereoselectivities (avg 15:1) to furnish products regioisomeric from those previously obtained using allylic C-H amination reactions. Mechanistic studies suggest the role of the phosphoric acid is to furnish a Pd(II)bis-sulfoxide phosphate catalyst that promotes allylic C-H cleavage and π-allylPd functionalization with a weak, aprotic oxygen nucleophile and to assist in catalyst regeneration.
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