ArticleJournal of the American Chemical Society2013
Catalyst-controlled C-O versus C-N allylic functionalization of terminal olefins.
Article in Journal of the American Chemical Society, 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 16 papers.
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Who cites it
16 citing papers in PubMed, 119 citations in OpenAlex.
- Electrooxidative Divergent Halocyclizations of Ambident Amides.Angewandte Chemie (International ed. in English) · 2026Article
- Counterintuitive chemoselectivity in the reduction of carbonyl compounds.Nature reviews. Chemistry · 2024Review
- Strategies for AccessingMolecules (Basel, Switzerland) · 2024Review
- Chemoselectivity change in catalytic hydrogenolysis enabling urea-reduction to formamide/amine over more reactive carbonyl compounds.Nature communications · 2023Article
- Diastereoconvergent synthesis ofChemical science · 2022Article
- C-H Activation: Toward Sustainability and Applications.ACS central science · 2021Review
- Intramolecular C(spAngewandte Chemie (International ed. in English) · 2020Article
- Palladium-Catalyzed Oxidation of β-C(spJournal of the American Chemical Society · 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
- Enantioselective Organocatalytic Amine-Isocyanate Capture-Cyclization: Regioselective Alkene Iodoamination for the Synthesis of Chiral Cyclic Ureas.ACS catalysis · 2018Article
- Synthesis of N-H Bearing Imidazolidinones and Dihydroimidazolones Using Aza-Heck Cyclizations.Angewandte Chemie (International ed. in English) · 2018Article
- OPolyhedron · 2014Article
- Terminal olefins to chromans, isochromans, and pyrans via allylic C-H oxidation.Journal of the American Chemical Society · 2014Article
- N-Boc amines to oxazolidinones via Pd(II)/bis-sulfoxide/Brønsted acid co-catalyzed allylic C-H oxidation.Journal of the American Chemical Society · 2014Article
- General allylic C-H alkylation with tertiary nucleophiles.Journal of the American Chemical Society · 2014Article
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2 authors at 1 institution in 1 country.
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Abstract
The divergent synthesis of syn-1,2-aminoalcohol or syn-1,2-diamine precursors from a common terminal olefin has been accomplished using a combination of palladium(II) catalysis with Lewis acid cocatalysis. Palladium(II)/bis-sulfoxide catalysis with a silver triflate cocatalyst leads for the first time to anti-2-aminooxazolines (C-O) in good to excellent yields. Simple removal of the bis-sulfoxide ligand from this reaction results in a complete switch in reactivity to afford anti-imidazolidinone products (C-N) in good yields and excellent diastereoselectivities. Mechanistic studies suggest the divergent C-O versus C-N reactivity from a common ambident nucleophile arises due to a switch in mechanism from allylic C-H cleavage/functionalization to olefin isomerization/oxidative amination.
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