Nickel/biimidazole-catalyzed electrochemical enantioselective reductive cross-coupling of aryl aziridines with aryl iodides

Yun-Zhao Wang, Zhen-Hua Wang, Inbal L. Eshel, Bing Sun, Dong Liu, Yu-Cheng Gu, Anat Milo () and Tian-Sheng Mei ()
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Yun-Zhao Wang: University of Chinese Academy of Sciences, CAS
Zhen-Hua Wang: University of Chinese Academy of Sciences, CAS
Inbal L. Eshel: Ben-Gurion University of the Negev
Bing Sun: University of Chinese Academy of Sciences, CAS
Dong Liu: University of Chinese Academy of Sciences, CAS
Yu-Cheng Gu: Syngenta, Jealott’s Hill International Research Centre
Anat Milo: Ben-Gurion University of the Negev
Tian-Sheng Mei: University of Chinese Academy of Sciences, CAS

Nature Communications, 2023, vol. 14, issue 1, 1-10

Abstract: Abstract 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.

Date: 2023
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DOI: 10.1038/s41467-023-37965-0

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