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

作者：Wang, Maorui; Zhang, Chengqian; Ci, Chenggang^*; Jiang, Huanfeng; Dixneuf, Pierre. H.; Zhang, Min^*

来源：Journal of the American Chemical Society, 2023, 145(20): 10967-10973.

DOI：10.1021/jacs.3c02776

• C-H ACTIVATION
• AMINOHYDROXYLATION
• ELECTROCHEMISTRY
• ALKENES
• OLEFINS

Despitethe widespread applications of alpha-hydroxyalkyl cyclicamines, direct and diverse access to such a class of unique vicinalamino alcohols still remains, to date, a challenge. Here, througha strategy of electroreductive alpha-hydroxyalkylation of inactive N-heteroarenes with ketones or electron-rich arylaldehydes,we describe a room temperature approach for the direct constructionof alpha-hydroxyalkyl cyclic amines, which features a broad substratescope, operational simplicity, high chemoselectivity, and no needfor pressurized H-2 gas and transition metal catalysts.The zinc ion generated from anode oxidation plays a crucial role inthe activation of both reactants by decreasing their reduction potentials.The strategy of electroreduction in combination with substrate activationby Lewis acids in this work is anticipated to develop more usefultransformations.