Nature Communications ( IF 14.7 ) Pub Date : 2023-04-22 , DOI: 10.1038/s41467-023-37965-0 Yun-Zhao Wang 1 , Zhen-Hua Wang 1 , Inbal L Eshel 2 , Bing Sun 1 , Dong Liu 1 , Yu-Cheng Gu 3 , Anat Milo 2 , Tian-Sheng Mei 1
Here, we report an asymmetric electrochemical organonickel-catalyzed reductive cross-coupling of aryl aziridines with aryl iodides in an undivided cell, affording β-phenethylamines in good to excellent enantioselectivity with broad functional group tolerance. The combination of cyclic voltammetry analysis of the catalyst reduction potential as well as an electrode potential study provides a convenient route for reaction optimization. Overall, the high efficiency of this method is credited to the electroreduction-mediated turnover of the nickel catalyst instead of a metal reductant-mediated turnover. Mechanistic studies suggest a radical pathway is involved in the ring opening of aziridines. The statistical analysis serves to compare the different design requirements for photochemically and electrochemically mediated reactions under this type of mechanistic manifold.
中文翻译:
镍/联咪唑催化芳基氮丙啶与芳基碘化物的电化学对映选择性还原交叉偶联
在这里,我们报告了在未分隔的电池中芳基氮丙啶与芳基碘化物的不对称电化学有机镍催化的还原交叉偶联,提供β-苯乙胺具有良好到极佳的对映选择性,具有广泛的官能团耐受性。催化剂还原电位的循环伏安法分析与电极电位研究相结合,为反应优化提供了便利的途径。总的来说,这种方法的高效率归功于镍催化剂的电还原介导的周转,而不是金属还原剂介导的周转。机理研究表明氮丙啶的开环涉及自由基途径。统计分析用于比较这种类型的机械流形下光化学和电化学介导反应的不同设计要求。