ArticleJournal of the American Chemical Society2014
Terminal olefins to chromans, isochromans, and pyrans via 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 14 papers.
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Who cites it
14 citing papers in PubMed.
- Allylic C-H oxygenation of unactivated internal olefins by the Cu/azodiformate catalyst system.Nature communications · 2025Article
- An Organometallic Umpolung Approach for Iron-Mediated Propargylic C-H Etherification.Angewandte Chemie (International ed. in English) · 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
- Synthesis of sulfonyl 2-aryl-5-methylenyltetrahydropyrans.RSC advances · 2023Article
- Selective radical cascade (4+2) annulation with olefins towards the synthesis of chroman derivativesChemical science · 2022Article
- Copper-catalyzed enantioselective alkene carboetherification for the synthesis of saturated six-membered cyclic ethers.Chemical communications (Cambridge, England) · 2021Article
- Enantioenriched α-Vinyl 1,4-Benzodiazepines and 1,4-Benzoxazepines via Enantioselective Rhodium-Catalyzed Hydrofunctionalizations of Alkynes and Allenes.The Journal of organic chemistry · 2021Article
- C-H Functionalization via Iron-Catalyzed Carbene-Transfer Reactions.Molecules (Basel, Switzerland) · 2020Review
- Dirhodium tetracarboxylates as catalysts for selective intermolecular C-H functionalization.Nature reviews. Chemistry · 2019Article
- Stereoselective Dynamic Cyclization of Allylic Azides: Synthesis of Tetralins, Chromanes, and Tetrahydroquinolines.Journal of the American Chemical Society · 2018Article
- Catalytic, Enantioselective, Intramolecular Sulfenofunctionalization of Alkenes with Phenols.The Journal of organic chemistry · 2017Article
- 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
Corrections and comments
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Authors and funding
3 authors.
Funding
Abstract
The synthesis of chroman, isochroman, and pyran motifs has been accomplished via a combination of Pd(II)/bis-sulfoxide C-H activation and Lewis acid co-catalysis. A wide range of alcohols are found to be competent nucleophiles for the transformation under uniform conditions (catalyst, solvent, temperature). Mechanistic studies suggest that the reaction proceeds via initial C-H activation followed by a novel inner-sphere functionalization pathway. Consistent with this, the reaction shows reactivity trends orthogonal to those of traditional Pd(0)-catalyzed allylic substitutions.
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