Rhodium(II)‐Catalyzed Oxo‐Amination of Aryl Cyclopropanes

A rhodium(II)‐catalyzed method is described for synthesizing β‐amino ketones from aryl cyclopropanes, utilizing water as an oxygen source and N ‐fluorobis(benzenesulfonamide) as a commercially available nitrogen source. This approach offers good substrate tolerance under mild conditions, providing a novel and practical route for β‐amino ketone synthesis. Mechanistic studies reveal a sequential cascade pathway initiated by single‐electron transfer facilitated by the rhodium(II) catalyst, followed by hydrogen atom transfer and radical polar crossover steps. These insights underscore the potential of rhodium(II) in driving radical amination reactions, enhancing the synthesis of β‐amino ketones from simple precursors.

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Publication Details

Journal
European Journal of Organic Chemistry
Published
2025-04-08
DOI
https://doi.org/10.1002/ejoc.202500235
Citations
1
Primary Topic
Cyclopropane Reaction Mechanisms
Type
article
Field-Weighted Citation Impact
0.94

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article

Rhodium(II)‐Catalyzed Oxo‐Amination of Aryl Cyclopropanes

Yuanhua Wang, Nengde Liang, Zhiying Fan
1 citations
European Journal of Organic Chemistry
Cyclopropane Reaction Mechanisms
0.94
article

Rhodium(II)‐Catalyzed Oxo‐Amination of Aryl Cyclopropanes

Yuanhua Wang, Nengde Liang, Zhiying Fan
article en
1 citations

Abstract

A rhodium(II)‐catalyzed method is described for synthesizing β‐amino ketones from aryl cyclopropanes, utilizing water as an oxygen source and N ‐fluorobis(benzenesulfonamide) as a commercially available nitrogen source. This approach offers good substrate tolerance under mild conditions, providing a novel and practical route for β‐amino ketone synthesis. Mechanistic studies reveal a sequential cascade pathway initiated by single‐electron transfer facilitated by the rhodium(II) catalyst, followed by hydrogen atom transfer and radical polar crossover steps. These insights underscore the potential of rhodium(II) in driving radical amination reactions, enhancing the synthesis of β‐amino ketones from simple precursors.

European Journal of Organic ChemistryVol. 28(23)
Xihua University (CN), Sichuan University (CN)
National Science Foundation, National Natural Science Foundation of China
Openalex Percentile: Top 27%
Cyclopropane Reaction Mechanisms
0.94
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Rhodium(II)‐Catalyzed Oxo‐Amination of Aryl Cyclopropanes — Yuanhua Wang, Nengde Liang, et al. · European Journal of Organic Chemistry (2025) | TGRS Research Map | TGRS