Room Temperature Construction of Vicinal Amino Alcohols via Electroreductive Cross-Coupling of N-Heteroarenes and Carbonyls - Université de Rennes Accéder directement au contenu
Article Dans Une Revue Journal of the American Chemical Society Année : 2023

Room Temperature Construction of Vicinal Amino Alcohols via Electroreductive Cross-Coupling of N-Heteroarenes and Carbonyls

Résumé

Despite the widespread applications of α-hydroxyalkyl cyclic amines, direct and diverse access to such a class of unique vicinal amino alcohols still remains, to date, a challenge. Here, through a strategy of electroreductive α-hydroxyalkylation of inactive N-heteroarenes with ketones or electron-rich arylaldehydes, we describe a room temperature approach for the direct construction of α-hydroxyalkyl cyclic amines, which features a broad substrate scope, operational simplicity, high chemoselectivity, and no need for pressurized H(2) gas and transition metal catalysts. The zinc ion generated from anode oxidation plays a crucial role in the activation of both reactants by decreasing their reduction potentials. The strategy of electroreduction in combination with substrate activation by Lewis acids in this work is anticipated to develop more useful transformations.

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Chimie
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Dates et versions

hal-04088953 , version 1 (04-05-2023)

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Maorui Wang, Chengqian Zhang, Chenggang Ci, Huanfeng Jiang, Pierre H. Dixneuf, et al.. Room Temperature Construction of Vicinal Amino Alcohols via Electroreductive Cross-Coupling of N-Heteroarenes and Carbonyls. Journal of the American Chemical Society, 2023, ⟨10.1021/jacs.3c02776⟩. ⟨hal-04088953⟩
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