Utilizing Nitroarenes and HCHO to Directly Construct Functional N-Heterocycles by Supported Cobalt/Amino Acid Relay Catalysis - Organométalliques : Matériaux et Catalyse Accéder directement au contenu
Article Dans Une Revue Angewandte Chemie International Edition Année : 2023

Utilizing Nitroarenes and HCHO to Directly Construct Functional N-Heterocycles by Supported Cobalt/Amino Acid Relay Catalysis

Résumé

Due to the generation of multiple intermediates during the nitroarene reduction, precise interception of single one to develop tandem reactions involving both C-C and C-N bond formations still remains a significant challenge. Herein, the relay catalysis of a supported bifunctional cobalt catalyst with L-proline has been successfully applied to establish a bran-new reductive annulation reaction of nitroarenes and formaldehyde, which enables direct and diverse construction of both symmetrical and unsymmetrical 1,3-diaryl imidazolines. It proceeds with operational simplicity, good substrate and functionality compatibility, and excellent step and atom-efficiency. Mechanistic studies reveal that the Co-catalyst exhibits a synergistic effect on the formation of key N-hydroxy imine, and the L-proline subsequently facilitates the key C-C bond formation. The current work opens a door to develop useful transformations with nitroarenes by reduction-interrupted strategy.
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Dates et versions

hal-04061790 , version 1 (16-05-2023)

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Paternité - Pas d'utilisation commerciale

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Jialu Sun, Chenggang Ci, Huanfeng Jiang, Pierre H. Dixneuf, Min Zhang. Utilizing Nitroarenes and HCHO to Directly Construct Functional N-Heterocycles by Supported Cobalt/Amino Acid Relay Catalysis. Angewandte Chemie International Edition, 2023, 62 (22), pp.e202303007. ⟨10.1002/anie.202303007⟩. ⟨hal-04061790⟩
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