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Updated: Dec 21, 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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Arene dearomatization through a catalytic N-centered radical cascade reaction
Rory C McAtee1, Efrey A Noten1, Corey R J Stephenson2
1Willard Henry Dow Laboratory, Department of Chemistry, University of Michigan, 930 North University Ave., Ann Arbor, MI, 48109, USA.
Nature Communications
|May 21, 2020
Summary
This study introduces a new catalytic method for arene dearomatization, creating complex 3D molecules from simple aromatic building blocks using visible light. The process efficiently forms sultams through a carboamination/dearomatization cascade.
Area of Science:
- Organic Chemistry
- Synthetic Methodology
- Photocatalysis
Background:
- Arene dearomatization is crucial for synthesizing complex molecular structures.
- Developing efficient catalytic methods for dearomatization remains an active area of research.
Purpose of the Study:
- To develop a novel catalytic protocol for arene dearomatization via a carboamination/dearomatization cascade.
- To utilize native sulfonamide N-H bonds for generating transient sulfonamidyl radical intermediates.
Main Methods:
- Employing an iridium(III) photocatalyst and a dialkyl phosphate base.
- Utilizing visible light irradiation at room temperature.
- Investigating reaction optimization, substrate scope, and mechanistic pathways.
Main Results:
- Successful demonstration of a catalytic carboamination/dearomatization cascade.
- Formation of 1,4-cyclohexadiene-fused sultams from aromatic compounds.
- Generation of richly substituted, three-dimensional compounds.
Conclusions:
- This work presents a facile and efficient method for synthesizing complex 3D molecules from 2D aromatic precursors.
- The developed protocol offers a valuable tool for organic synthesis and drug discovery.
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