Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510641, China.
Key Laboratory of Computational Catalytic Chemistry of Guizhou Province, Department of Chemistry and Chemical Engineering, Qiannan Normal University for Nationalities, Duyun 558000, China.
J Am Chem Soc. 2023 May 24;145(20):10967-10973. doi: 10.1021/jacs.3c02776. Epub 2023 Apr 19.
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 -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 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.
尽管 α-羟烷基环胺有广泛的应用，但直接和多样化地获得此类独特的偕氨基醇仍然是一个挑战。在这里，我们通过酮或富电子芳醛与惰性杂芳烃的电还原 α-羟烷基化反应策略，描述了一种在室温下直接构建 α-羟烷基环胺的方法，该方法具有广泛的底物范围、操作简单、高化学选择性，并且不需要加压 H2 气体和过渡金属催化剂。阳极氧化产生的锌离子通过降低反应物的还原电位，在两种反应物的活化中起着关键作用。这项工作中，电还原策略与路易斯酸对底物的活化相结合，有望开发出更有用的转化。
