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Nickel-Catalyzed NO Group Transfer Coupled with NO Conversion
Sudakar Padmanaban1, Jonghoon Choi1, Hugo Vazquez-Lima2
1Department of Chemistry, Seoul National University, Seoul 08826, Republic of Korea.
Researchers developed a novel nickel catalyst for converting nitrogen oxide (NO) into valuable products. This synthetic approach achieves efficient deoxygenation and C-N coupling under mild conditions, producing oximes from benzyl halides.
Area of Science:
- Catalysis
- Organometallic Chemistry
- Green Chemistry
Background:
- Nitrogen oxide (NO) conversion is crucial for the global nitrogen cycle.
- Biological NO transformation is well-studied, but synthetic approaches are needed for value-added products.
Purpose of the Study:
- To devise a synthetic, bifunctional metal catalyst for NO conversion.
- To develop a novel nickel pincer system for efficient NO deoxygenation and C-N coupling.
Main Methods:
- Utilized a Ni pincer catalyst for NO deoxygenation using CO(g).
- Investigated the transfer of the nitroso group to organic substrates via nucleophilic reaction.
- Employed experimental and theoretical methods to evaluate the catalytic activation of alkyl halides.
Main Results:
- Successfully converted NO to Ni-NO and then to Ni-NO via deoxygenation.
- Achieved catalytic production of oximes from benzyl halides with a turnover number >200.
- Demonstrated a nickel(I)-NO species effectively activates alkyl halides.
Conclusions:
- The developed nickel catalyst is bifunctional, performing both NO deoxygenation and C-N coupling.
- This novel catalytic system offers a synthetic route to valuable products from NO under mild conditions.
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