Palladium-Catalyzed Aminocarbonylation Using Nitroarenes under NMP-Mediated Photochemical Conditions

A photochemical approach enabling mild amide synthesis from aryl iodides, carbon monoxide, and nitroarenes at 25 °C under 1 atm of CO is disclosed. Under a PdCl<sub>2</sub>/Xantphos-FeCl<sub>3</sub> catalyst in <i>N</i>-methylpyrrolidone, broad functional group tolerance is observed. Mechanistic studies reveal that nitroarenes form a base-activated <i>N</i>-methylpyrrolidone-bound adduct, which generates an aniline-like intermediate that couples with the acyl-palladium complex to deliver the desired amides.

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Publication Details

Journal
Organic Letters
Published
2025-06-13
DOI
https://doi.org/10.1021/acs.orglett.5c01619
Citations
2
Primary Topic
Chemical Synthesis and Analysis
Type
article
Field-Weighted Citation Impact
1.61

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article

Palladium-Catalyzed Aminocarbonylation Using Nitroarenes under NMP-Mediated Photochemical Conditions

Sunwoo Lee, Minwoo Park, Karthik Rajan Rajamanickam
2 citations
Organic Letters
Chemical Synthesis and Analysis
1.61
article

Palladium-Catalyzed Aminocarbonylation Using Nitroarenes under NMP-Mediated Photochemical Conditions

Sunwoo Lee, Minwoo Park, Karthik Rajan Rajamanickam
article en
2 citations

Abstract

A photochemical approach enabling mild amide synthesis from aryl iodides, carbon monoxide, and nitroarenes at 25 °C under 1 atm of CO is disclosed. Under a PdCl<sub>2</sub>/Xantphos-FeCl<sub>3</sub> catalyst in <i>N</i>-methylpyrrolidone, broad functional group tolerance is observed. Mechanistic studies reveal that nitroarenes form a base-activated <i>N</i>-methylpyrrolidone-bound adduct, which generates an aniline-like intermediate that couples with the acyl-palladium complex to deliver the desired amides.

Organic LettersVol. 27(25)
Chonnam National University Hospital (KR)
National Research Foundation of Korea
Openalex Percentile: Top 17%
Chemical Synthesis and Analysis
1.61
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