ArticleJournal of the American Chemical Society2016
Ligand-Enabled γ-C(sp(3))-H Olefination of Amines: En Route to Pyrrolidines.
Article in Journal of the American Chemical Society, 2016. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 33 papers.
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Who cites it
33 citing papers in PubMed, 138 citations in OpenAlex.
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- Tunable [3+2] and [4+2] annulations for pyrrolidine and piperidine synthesis.Chemical communications (Cambridge, England) · 2023Article
- Facile Synthesis of Functionalized Phenoxy Quinolines: Antibacterial Activities against ESBL ProducingMolecules (Basel, Switzerland) · 2022Article
- Transition-Metal-Catalyzed Annulations Involving the Activation of C(spAngewandte Chemie (International ed. in English) · 2022Review
- Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(spChemical reviews · 2021Review
- Assembly of Tetrahydroquinolines and 2-Benzazepines by Pd-Catalyzed Cycloadditions Involving the Activation of C(spOrganic letters · 2021Article
- Recent development in transition metal-catalysed C-H olefination.Chemical science · 2021Review
- Metal-free C(spChemical science · 2021Article
- Tailored quinones support high-turnover Pd catalysts for oxidative C-H arylation with OScience (New York, N.Y.) · 2020Article
- Diverse strategies for transition metal catalyzed distal C(spChemical science · 2020Review
- Distal γ-C(spAngewandte Chemie (International ed. in English) · 2020Article
- Pd(II)-Catalyzed Enantioselective γ-C(spJournal of the American Chemical Society · 2020Article
- Photoinduced site-selective alkenylation of alkanes and aldehydes with aryl alkenes.Nature communications · 2020Article
- A General Acid-Mediated Hydroaminomethylation of Unactivated Alkenes and Alkynes.Angewandte Chemie (International ed. in English) · 2019Article
- Hemilabile Benzyl Ether Enables γ-C(spJournal of the American Chemical Society · 2019Article
- Utilizing Carbonyl Coordination of Native Amides for Palladium-Catalyzed C(spAngewandte Chemie (International ed. in English) · 2019Article
- Aliphatic Radical Relay Heck Reaction at Unactivated C(spAngewandte Chemie (International ed. in English) · 2019Article
- Copper-Catalyzed Coupling of Thioamides and Donor/Acceptor-Substituted Carbenoids: Synthesis of Enamino Esters and Enaminones.ACS omega · 2019Article
Corrections and comments
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Authors and funding
4 authors at 1 institution in 1 country.
Funding
Abstract
Pd(II)-catalyzed olefination of γ-C(sp(3))-H bonds of triflyl (Tf) and 4-nitrobenzenesulfonyl (Ns) protected amines is achieved. Subsequent aza-Wacker oxidative cyclization or conjugate addition of the olefinated intermediates provides a variety of C-2 alkylated pyrrolidines. Three pyridine- and quinoline-based ligands are developed to match different classes of amine substrates, demonstrating a rare example of ligand-enabled C(sp(3))-H olefination reactions. The use of Ns protecting group to direct C(sp(3))-H activation of alkyl amines is also a significant step toward practical C-H functionalizations of alkyl amines.
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Registered trials
Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.