ArticleJournal of the American Chemical Society2017
Copper-Catalyzed Alkene Aminoazidation as a Rapid Entry to 1,2-Diamines and Installation of an Azide Reporter onto Azahetereocycles.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 19 papers.
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Who cites it
19 citing papers in PubMed.
- Copper-Catalyzed 1,2-Diazidation and 1,2-Azidooxygenation of 1,3-Dienes: Three Divergent Protocols Using Zhdankin's Reagent.The Journal of organic chemistry · 2025Article
- TetheredTetrahedron · 2025Article
- Transformation of Linear AlkenylChemistry (Basel, Switzerland) · 2025Article
- Rh(III)-Catalyzed AlkeneACS catalysis · 2024Article
- Enantioselective copper-catalyzed azidation/click cascade reaction for access to chiral 1,2,3-triazoles.Nature communications · 2024Article
- Ring Opening of Aziridines by Pendant Sulfamates Allows for Regioselective and Stereospecific Preparation of Vicinal Diamines.The Journal of organic chemistry · 2023Article
- Modular and practical diamination of allenes.Nature communications · 2023Article
- The advent of electrophilic hydroxylamine-derived reagents for the direct preparation of unprotected amines.Chemical communications (Cambridge, England) · 2022Review
- Practical Synthesis of 2-Iodosobenzoic Acid (IBA) without Contamination by Hazardous 2-Iodoxybenzoic Acid (IBX) under Mild Conditions.Molecules (Basel, Switzerland) · 2021Article
- Preparation of cyclic imides from alkene-tethered amides: application of homogeneous Cu(ii) catalytic systems.RSC advances · 2020Article
- Copper-Promoted Functionalization of Organic Molecules: from Biologically Relevant Cu/OChemical reviews · 2019Review
- Aminoxyl-Catalyzed Electrochemical Diazidation of Alkenes Mediated by a Metastable Charge-Transfer Complex.Journal of the American Chemical Society · 2019Article
- Copper-Catalyzed Modular Amino Oxygenation of Alkenes: Access to Diverse 1,2-Amino Oxygen-Containing Skeletons.The Journal of organic chemistry · 2019Article
- 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
- Pd-Catalyzed Alkene Diamination Reactions of Nitrogen Electrophiles: Synthesis of Cyclic Guanidines and Ureas Bearing Dialkylaminomethyl Groups.Organic letters · 2018Article
- Iron-Catalyzed Direct Olefin Diazidation via Peroxyester Activation Promoted by Nitrogen-Based Ligands.ACS catalysis · 2018Article
- Regiodivergent Iridium(III)-Catalyzed Diamination of Alkenyl Amides with Secondary Amines: Complementary Access to γ- or δ-Lactams.Journal of the American Chemical Society · 2018Article
- Copper-catalyzed aminoalkynylation of alkenes with hypervalent iodine reagents.Chemical science · 2017Article
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Abstract
A copper-catalyzed aminoazidation of unactivated alkenes is achieved for the synthesis of versatile unsymmetrical 1,2-diamine derivatives. This transformation offers an effective approach to installing an amide and an azide from two diffenent amino precursors onto both terminal and internal alkenes, with remarkable regio- and stereoselectivity. Mechanistic studies show that this diamination reaction proceeds via a nucleophilic amino cyclization followed by an intermolecular C-N bond formation using electrophilic azidoiodinane. This pathway differs from previous azidoiodinane-initiated alkene functionalization, suggesting new reactivity of azidoiodinane. Furthermore, this aminoazidation reaction provides an efficient strategy to introduce azide, one of the most useful chemical reporters, onto a broad range of bioactive azaheterocycles, offering new opportunities in bioorthogonal chemistry and biological studies. Rapid syntheses of 5-HT
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