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

Autor: Jia‐Lu Sun, Chenggang Ci, Huanfeng Jiang, Pierre H. Dixneuf, Min Zhang
Přispěvatelé: South China University of Technology [Guangzhou] (SCUT), Qiannan Normal College for Nationalities [Duyun] (QNCN), Institut des Sciences Chimiques de Rennes (ISCR), Université de Rennes (UR)-Institut National des Sciences Appliquées - Rennes (INSA Rennes), Institut National des Sciences Appliquées (INSA)-Institut National des Sciences Appliquées (INSA)-Ecole Nationale Supérieure de Chimie de Rennes (ENSCR)-Institut de Chimie du CNRS (INC)-Centre National de la Recherche Scientifique (CNRS), The authors are grateful to the financial support of State Key Laboratoryof Pulp and Paper Engineering (2022C03), the National Natural Science Foundation of China (21971071, 22163007), the Natural Science Foundation of Guangdong Province (2023A1515012318 and2021A1515010155), and Guizhou Province Science Foundation ([2020]1Y050).
Jazyk: angličtina
Rok vydání: 2023
Předmět:
Zdroj: Angewandte Chemie International Edition
Angewandte Chemie International Edition, 2023, 62 (22), pp.e202303007. ⟨10.1002/anie.202303007⟩
ISSN: 1433-7851
1521-3773
DOI: 10.1002/anie.202303007⟩
Popis: International audience; 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.
Databáze: OpenAIRE
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