Room Temperature Construction of Vicinal Amino Alcohols via Electroreductive Cross-Coupling of N-Heteroarenes and Carbonyls,Journal of the American Chemical Society

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Room Temperature Construction of Vicinal Amino Alcohols via Electroreductive Cross-Coupling of N-Heteroarenes and Carbonyls
Journal of the American Chemical Society ( IF 14.4 ) Pub Date : 2023-04-19 , DOI: 10.1021/jacs.3c02776
Maorui Wang ₁ , Chengqian Zhang ₁ , Chenggang Ci ₂ , Huanfeng Jiang ₁ , Pierre H Dixneuf ₃ , Min Zhang ₁

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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 H₂ 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.

中文翻译：

N-杂芳烃和羰基的电还原交叉偶联室温构建邻氨基醇

尽管 α-羟烷基环胺具有广泛的应用，但迄今为止，直接和多样化地获取此类独特的邻位氨基醇仍然是一个挑战。在这里，通过用酮或富电子芳醛对非活性 N-杂芳烃进行电还原 α-羟烷基化的策略，我们描述了一种用于直接构建 α-羟烷基环胺的室温方法，该方法具有广泛的底物范围、操作简单、高化学选择性，无需加压 H ₂气体和过渡金属催化剂。阳极氧化产生的锌离子通过降低它们的还原电位在两种反应物的活化中起着至关重要的作用。在这项工作中，电还原策略与路易斯酸的底物激活相结合，有望开发出更有用的转化。

更新日期：2023-04-19

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