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Access to Carbonyl Azides via Iodine(III)-Mediated Cross-Coupling.
1School of Chemistry and Materials Science, Jiangsu Key Laboratory of Green Synthesis for Functional Materials, Jiangsu Normal University, Xuzhou, Jiangsu 221116, China.
Organic Letters
|October 17, 2024
Summary
This study introduces a metal-free C-N cross-coupling method using an iodine(III) promoter. The process efficiently synthesizes carbamoyl- and ketoazides from isocyanides or silyl enol ethers and trimethylsilyl azide.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
- Catalysis
Background:
- Metal-free cross-coupling reactions are crucial for sustainable synthesis.
- Azide-containing compounds are valuable synthetic intermediates.
- Efficient methods for synthesizing carbamoyl- and ketoazides are needed.
Purpose of the Study:
- To develop a novel metal-free C-N cross-coupling platform.
- To enable the synthesis of carbamoyl- and ketoazides.
- To utilize trimethylsilyl azide (TMSN3) for azide incorporation.
Main Methods:
- Employing an iodine(III) promoter for C-N cross-coupling.
- Reacting isocyanides or silyl enol ethers with trimethylsilyl azide (TMSN3).
- Metal-free reaction conditions.
Main Results:
- Successful synthesis of carbamoyl- and ketoazides.
- Excellent substrate scope and good to excellent yields achieved.
- Demonstrated efficient incorporation of the azide fragment using TMSN3 without N2 loss.
Conclusions:
- The developed platform provides a rapid and efficient route to azide-decorated fragments.
- This metal-free approach offers a valuable tool for synthetic chemists.
- Highlights the utility of TMSN3 in C-N cross-coupling reactions.
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