Iron-Assisted and Cu-Mediated Direct Aminocarbonylation of Nitroarene with Boronic Acid

Herein, we have established the formation of diaryl amide by aminocarbonylation of nitrobenzene with boronic acids. The method works in the catalytic presence of economical and commercially available CuI salt, which was significantly promoted by the Fe<sub>3</sub>Se<sub>2</sub>(CO)<sub>9</sub> cluster. Mo(CO)<sub>6</sub> serves as a source of CO, and it also acts as a reductant with a combination of iron cluster. Moreover, all the reaction worked under the ligand-free system and produced the desired diaryl amide in a significant time of 10 h. Water, a green solvent, was used as a source of hydrogen for the reduction of nitrobenzene to aniline. The method depicts a suitable functional group tolerance and produces a wide range of substrates in good to excellent amounts. To the best of our knowledge, this is the first report for the direct aminocarbonylation mediated by highly economical CuI. Moreover, water as a source of hydrogen for the reduction of nitroarene is always appreciated.

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Journal
The Journal of Organic Chemistry
Published
2024-12-24
DOI
https://doi.org/10.1021/acs.joc.4c02232
Primary Topic
Asymmetric Hydrogenation and Catalysis
Type
article
Field-Weighted Citation Impact
0.00

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article

Iron-Assisted and Cu-Mediated Direct Aminocarbonylation of Nitroarene with Boronic Acid

Sangeeta Kumari, Raj K. Joshi, Charu Sharma, Deepak Sharma
The Journal of Organic Chemistry
Asymmetric Hydrogenation and Catalysis
article

Iron-Assisted and Cu-Mediated Direct Aminocarbonylation of Nitroarene with Boronic Acid

Sangeeta Kumari, Raj K. Joshi, Charu Sharma, Deepak Sharma
article en

Abstract

Herein, we have established the formation of diaryl amide by aminocarbonylation of nitrobenzene with boronic acids. The method works in the catalytic presence of economical and commercially available CuI salt, which was significantly promoted by the Fe<sub>3</sub>Se<sub>2</sub>(CO)<sub>9</sub> cluster. Mo(CO)<sub>6</sub> serves as a source of CO, and it also acts as a reductant with a combination of iron cluster. Moreover, all the reaction worked under the ligand-free system and produced the desired diaryl amide in a significant time of 10 h. Water, a green solvent, was used as a source of hydrogen for the reduction of nitrobenzene to aniline. The method depicts a suitable functional group tolerance and produces a wide range of substrates in good to excellent amounts. To the best of our knowledge, this is the first report for the direct aminocarbonylation mediated by highly economical CuI. Moreover, water as a source of hydrogen for the reduction of nitroarene is always appreciated.

The Journal of Organic ChemistryVol. 90(5)
Malaviya National Institute of Technology Jaipur (IN)
Council of Scientific and Industrial Research, India, University Grants Commission
Clean water and sanitation
Openalex Percentile: Top 81%
Asymmetric Hydrogenation and Catalysis
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Iron-Assisted and Cu-Mediated Direct Aminocarbonylation of Nitroarene with Boronic Acid — Sangeeta Kumari, Raj K. Joshi, et al. · The Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS