ArticleChemistry (Weinheim an der Bergstrasse, Germany)2012
Evidence for alkene cis-aminocupration, an aminooxygenation case study: kinetics, EPR spectroscopy, and DFT calculations.
Article in Chemistry (Weinheim an der Bergstrasse, Germany), 2012. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 25 papers.
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25 citing papers in PubMed, 71 citations in OpenAlex.
- Recent advances in copper-catalyzed direct hydroamination of alkenes with (hetero)aromatic amines.Beilstein journal of organic chemistry · 2026Review
- Incorporating azaheterocycle functionality in intramolecular aerobic, copper-catalyzed aminooxygenation of alkenes.RSC advances · 2024Article
- Copper-catalyzed generation of nitrogen-centered radicals and reactions thereof.ARKIVOC : free online journal of organic chemistry · 2024Article
- Copper-Catalyzed Hydroamination: Enantioselective Addition of Pyrazoles to Cyclopropenes.Journal of the American Chemical Society · 2023Article
- Copper-Catalyzed Enantioselective Aerobic Alkene Aminooxygenation and Dioxygenation: Access to 2-Formyl Saturated Heterocycles and Unnatural Proline Derivatives.Journal of the American Chemical Society · 2023Article
- Alkynoates as Versatile and Powerful Chemical Tools for the Rapid Assembly of Diverse Heterocycles under Transition-Metal Catalysis: Recent Developments and Challenges.Topics in current chemistry (Cham) · 2021Review
- Preparation of cyclic imides from alkene-tethered amides: application of homogeneous Cu(ii) catalytic systems.RSC advances · 2020Article
- Stereoselective and Regioselective Synthesis of Heterocycles via Copper-Catalyzed Additions of Amine Derivatives and Alcohols to Alkenes.The Journal of organic chemistry · 2017Article
- Direct Synthesis of 2-Formylpyrrolidines, 2-Pyrrolidinones and 2-Dihydrofuranones via Aerobic Copper-Catalyzed Aminooxygenation and Dioxygenation of 4-Pentenylsulfonamides and 4-Pentenylalcohols.Journal of the American Chemical Society · 2017Article
- Stereoselective Synthesis of Isoxazolidines via Copper-Catalyzed Alkene Diamination.ACS catalysis · 2017Article
- Catalytic, Stereoselective Dihalogenation of Alkenes: Challenges and Opportunities.Angewandte Chemie (International ed. in English) · 2015Review
- Copper(II)-Promoted Cyclization/Difunctionalization of Allenols and Allenylsulfonamides: Synthesis of Heterocycle-Functionalized Vinyl Carboxylate Esters.Organic letters · 2015Article
- Copper-catalyzed diamination of unactivated alkenes with hydroxylamines.Chemical science · 2015Article
- Copper-promoted synthesis of 1,4-benzodiazepinones via alkene diamination.Tetrahedron letters · 2015Article
- Copper-Catalyzed Alkene Diamination: Synthesis of Chiral 2-Aminomethyl Indolines and Pyrrolidines.Chemical science · 2014Article
- A computational study of the copper(II)-catalyzed enantioselective intramolecular aminooxygenation of alkenes.The Journal of organic chemistry · 2013Article
- Copper-catalyzed oxidative amination and allylic amination of alkenes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2013Article
- Copper-catalyzed oxidative Heck reactions between alkyltrifluoroborates and vinyl arenes.Organic letters · 2013Article
- Mechanistic analysis and optimization of the copper-catalyzed enantioselective intramolecular alkene aminooxygenation.The Journal of organic chemistry · 2013Article
- Kinetic and Spectroscopic Studies of Aerobic Copper(II)-Catalyzed Methoxylation of Arylboronic Esters and Insights into Aryl Transmetalation to Copper(II).Organometallics · 2012Article
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Authors and funding
6 authors at 2 institutions in 2 countries.
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Abstract
Alkene difunctionalization reactions are important in organic synthesis. We have recently shown that copper(II) complexes can promote and catalyze intramolecular alkene aminooxygenation, carboamination, and diamination reactions. In this contribution, we report a combined experimental and theoretical examination of the mechanism of the copper(II)-promoted olefin aminooxygenation reaction. Kinetics experiments revealed a mechanistic pathway involving an equilibrium reaction between a copper(II) carboxylate complex and the γ-alkenyl sulfonamide substrate and a rate-limiting intramolecular cis-addition of N-Cu across the olefin. Kinetic isotope effect studies support that the cis-aminocupration is the rate-determining step. UV/Vis spectra support a role for the base in the break-up of copper(II) carboxylate dimer to monomeric species. Electron paramagnetic resonance (EPR) spectra provide evidence for a kinetically competent N-Cu intermediate with a Cu(II) oxidation state. Due to the highly similar stereochemical and reactivity trends among the Cu(II)-promoted and catalyzed alkene difunctionalization reactions we have developed, the cis-aminocupration mechanism can reasonably be generalized across the reaction class. The methods and findings disclosed in this report should also prove valuable to the mechanism analysis and optimization of other copper(II) carboxylate promoted reactions, especially those that take place in aprotic organic solvents.
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