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A Microwave-Assisted Direct Heteroarylation of Ketones Using Transition Metal Catalysis
Published on: February 16, 2020
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Aryne Aminohalogenation Using Protic Amines Enabled by Halogen Transfer.
Joshua T Gavin1, Lars W Anderson1, Courtney C Roberts1
1Department of Chemistry, University of Minnesota─Twin Cities, Minneapolis, Minnesota 55455, United States.
Organic Letters
|August 28, 2024
Summary
This study introduces a new method for aryne difunctionalization using halogen transfer reagents and protic amines. This approach overcomes limitations of previous methods, enabling efficient aminohalogenation of N-heterocyclic scaffolds.
Area of Science:
- Organic Chemistry
- Synthetic Methodology
Background:
- Aryne difunctionalization is a key area in synthetic organic chemistry.
- A significant limitation in current aryne difunctionalization methods involves the requirement for nucleophiles with proton sources.
- Developing new strategies to overcome this limitation is crucial for expanding the scope of aryne chemistry.
Purpose of the Study:
- To develop a novel method for aryne aminohalogenation difunctionalization.
- To enable the use of protic amines in aryne difunctionalization reactions.
- To demonstrate the broad applicability of the developed method to various N-heterocyclic scaffolds.
Main Methods:
- Utilizing halogen transfer reagents in conjunction with protic amines and arynes.
- Employing a range of N-heterocyclic scaffolds for the difunctionalization reactions.
- Characterization of the synthesized products and demonstration of their synthetic utility through derivatization.
Main Results:
- Successfully achieved aryne aminohalogenation difunctionalization using protic amines.
- Obtained yields of up to 86% for the desired difunctionalized products.
- Demonstrated the method's effectiveness with diverse N-heterocyclic amine substrates.
Conclusions:
- The developed method effectively overcomes the limitation of proton sources in aryne difunctionalization.
- This new protocol provides a valuable tool for the synthesis of complex molecules containing N-heterocyclic motifs.
- The synthetic utility of the products is confirmed through subsequent derivatization reactions.
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