ArticleChemistry (Weinheim an der Bergstrasse, Germany)2013
Copper-catalyzed oxidative amination and allylic amination of alkenes.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2013. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 13 papers.
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Who cites it
13 citing papers in PubMed.
- Copper-Catalyzed Allylic Amination of Alkenes UsingACS catalysis · 2025Article
- Copper-catalyzed generation of nitrogen-centered radicals and reactions thereof.ARKIVOC : free online journal of organic chemistry · 2024Article
- Copper-Catalyzed Intramolecular Olefinic C(spMolecules (Basel, Switzerland) · 2023Article
- Kinetic Resolution of β-Alkyl Phenylethylamine Derivatives through Palladium-Catalyzed, Nosylamide-Directed C-H Olefination.Molecules (Basel, Switzerland) · 2023Article
- Chemical Space Exploration of Oxetanes.International journal of molecular sciences · 2020Article
- Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes.The Journal of organic chemistry · 2017Article
- Stereoselective Synthesis of Isoxazolidines via Copper-Catalyzed Alkene Diamination.ACS catalysis · 2017Article
- Aryl amination using ligand-free Ni(II) salts and photoredox catalysis.Science (New York, N.Y.) · 2016Article
- Catalytic N-radical cascade reaction of hydrazones by oxidative deprotonation electron transfer and TEMPO mediation.Nature communications · 2016Article
- Recent advances in copper-catalyzed C-H bond amidation.Beilstein journal of organic chemistry · 2015Review
- Intermolecular addition reactions of N-alkyl-N-chlorosulfonamides to unsaturated compounds.Beilstein journal of organic chemistry · 2015Article
- Chemistry. Copper's contribution to amination catalysis.Science (New York, N.Y.) · 2013Article
- Copper-Catalyzed Synthesis ofSynlett : accounts and rapid communications in synthetic organic chemistryArticle
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2 authors.
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Abstract
Enamines and enamides are useful synthetic intermediates and common components of bioactive compounds. A new protocol for their direct synthesis by a net alkene C-H amination and allylic amination by using catalytic Cu(II) in the presence of MnO2 is reported. Reactions between N-aryl sulfonamides and vinyl arenes furnish enamides, allylic amines, indoles, benzothiazine dioxides, and dibenzazepines directly and efficiently. Control experiments further showed that MnO2 alone can promote the reaction in the absence of a copper salt, albeit with lower efficiency. Mechanistic probes support the involvement of nitrogen-radical intermediates. This method is ideal for the synthesis of enamides from 1,1-disubstituted vinyl arenes, which are uncommon substrates in existing oxidative amination protocols.
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