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Catalyst-Free Reductive Coupling of Aromatic and Aliphatic Nitro Compounds with Organohalides
Marian Rauser1, Raphael Eckert1, Max Gerbershagen1
1Institute of Organic Chemistry, RWTH Aachen, Landoltweg 1, 52072, Aachen, Germany.
Angewandte Chemie (International Ed. in English)
|March 13, 2019
Summary
A novel reductive coupling reaction efficiently converts nitro compounds and organohalides into monoalkylated amines. This catalyst-free method utilizes a nitrenoid intermediate, offering broad substrate scope for synthesizing valuable amine products.
Area of Science:
- Organic Chemistry
- Synthetic Chemistry
Background:
- Nitro compounds are versatile precursors in organic synthesis.
- Reductive coupling reactions are crucial for C-N bond formation.
- Existing methods for amine synthesis often require catalysts or specific conditions.
Purpose of the Study:
- To develop a new, efficient method for synthesizing monoalkylated amines.
- To explore the reductive coupling of nitro compounds with organohalides.
- To investigate a catalyst-free approach for amine synthesis.
Main Methods:
- Partial reduction of nitro compounds to generate a nitrenoid intermediate.
- Coupling of the nitrenoid intermediate with various organohalides.
- Utilizing both aromatic and aliphatic nitro compounds as substrates.
Main Results:
- Successful reductive coupling of nitro compounds with organohalides.
- Efficient transformation of nitro compounds into monoalkylated amines.
- Demonstrated high tolerance for aryl halide substituents.
- Catalyst-free reaction conditions achieved.
Conclusions:
- A rare and efficient reductive coupling of nitro compounds with organohalides has been achieved.
- The nitrenoid intermediate facilitates the formation of monoalkylated amines without a catalyst.
- This method provides a valuable new route for synthesizing diverse amines from readily available starting materials.
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