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Updated: Aug 6, 2025
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Facile Preparation of 2Z,4E-Dienamides by the Olefination of Electron-deficient Alkenes with Allyl Acetate
Published on: June 21, 2017
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Iron-Catalyzed Intermolecular Oxyamination of Terminal Alkenes Promoted by HFIP Using Hydroxylamine Derivatives
Georgina Kirby1, Guillaume Prestat1, Farouk Berhal1
1Laboratoire de Chimie et de Biochimie Pharmacologiques et Toxicologiques, Université Paris Cité, CNRS, F-75006 Paris, France.
The Journal of Organic Chemistry
|March 20, 2023
Summary
This study introduces an efficient iron-catalyzed oxyamination of alkenes, inserting oxygen and nitrogen from hydroxylamine. The reaction shows high selectivity for terminal alkenes, yielding oxyaminated products effectively.
Area of Science:
- Organic Chemistry
- Catalysis
- Green Chemistry
Background:
- Oxyamination of alkenes is a crucial transformation for synthesizing valuable nitrogen- and oxygen-containing organic molecules.
- Developing atom-economical and selective catalytic methods remains a significant challenge in organic synthesis.
Purpose of the Study:
- To develop an atom-economical intermolecular iron-catalyzed oxyamination of alkenes.
- To investigate the regio- and chemo-selectivity of the reaction for terminal alkenes.
- To explore the role of the solvent in the catalytic process.
Main Methods:
- Iron-catalyzed intermolecular oxyamination reaction using hydroxylamine as the nitrogen and oxygen source.
- Optimization of reaction conditions, including catalyst loading, solvent, and temperature.
- Analysis of reaction products using standard organic chemistry techniques (e.g., NMR, Mass Spectrometry).
Main Results:
- Achieved atom-economical intermolecular iron-catalyzed oxyamination of alkenes.
- Demonstrated full regio- and chemo-selectivity for terminal alkenes, affording oxyaminated products in good yields.
- Identified a synergistic effect between the iron catalyst and HFIP solvent in promoting product formation.
Conclusions:
- The developed iron-catalyzed oxyamination provides an efficient and selective route to oxyaminated alkenes.
- The use of HFIP as a solvent enhances the catalytic activity and selectivity of the iron catalyst.
- Preliminary mechanistic studies suggest a pathway involving aziridination followed by ring-opening.
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