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• W2095652694 endingPage "1726" @default.
• W2095652694 startingPage "1711" @default.
• W2095652694 abstract "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." @default.
• W2095652694 created "2016-06-24" @default.
• W2095652694 creator A5018970120 @default.
• W2095652694 creator A5042658700 @default.
• W2095652694 creator A5047612654 @default.
• W2095652694 creator A5056637127 @default.
• W2095652694 creator A5061360791 @default.
• W2095652694 creator A5082759843 @default.
• W2095652694 date "2012-01-11" @default.
• W2095652694 modified "2023-10-18" @default.
• W2095652694 title "Evidence for Alkene cis-Aminocupration, an Aminooxygenation Case Study: Kinetics, EPR Spectroscopy, and DFT Calculations" @default.
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