Merging Paired Electrolysis and Copper Catalysis Enables Electrochemical Arylation of Aziridine for the Synthesis of 1,2-Amino Tertiary Alcohols

1,2-Amino alcohols are omnipresent in bioactive molecules. Conventional approaches to this motif require multistep reactions. Herein, we develop an electrochemical strategy for copper-catalyzed convergent paired electrolysis. By selectively cleaving the C-N bond of 2-aryl-1-tosylaziridines with electron-deficient aromatics as the aryl source, the 1,2-amino tertiary alcohol scaffold is rapidly constructed. This method features mild reaction conditions, large-scale preparation, and a lack of sacrificial electrodes. Experimental studies and DFT calculations indicate that this reaction tends toward radical cross-coupling.

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Journal
Organic Letters
Published
2025-05-26
DOI
https://doi.org/10.1021/acs.orglett.5c01417
Primary Topic
Radical Photochemical Reactions
Type
article
Field-Weighted Citation Impact
0.00

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article

Merging Paired Electrolysis and Copper Catalysis Enables Electrochemical Arylation of Aziridine for the Synthesis of 1,2-Amino Tertiary Alcohols

Li‐Li Liao, Cheng‐He Zhou, Yu‐Rong Yang, Gui‐Xin Cai et al.
Organic Letters
Radical Photochemical Reactions
article

Merging Paired Electrolysis and Copper Catalysis Enables Electrochemical Arylation of Aziridine for the Synthesis of 1,2-Amino Tertiary Alcohols

Li‐Li Liao, Cheng‐He Zhou, Yu‐Rong Yang, Gui‐Xin Cai, Zhong‐Lin Zang, Xin-Yu Zhang, Dexin Xie, Zhong-Shan Teng
article en

Abstract

1,2-Amino alcohols are omnipresent in bioactive molecules. Conventional approaches to this motif require multistep reactions. Herein, we develop an electrochemical strategy for copper-catalyzed convergent paired electrolysis. By selectively cleaving the C-N bond of 2-aryl-1-tosylaziridines with electron-deficient aromatics as the aryl source, the 1,2-amino tertiary alcohol scaffold is rapidly constructed. This method features mild reaction conditions, large-scale preparation, and a lack of sacrificial electrodes. Experimental studies and DFT calculations indicate that this reaction tends toward radical cross-coupling.

Organic LettersVol. 27(22)
Southwest University (CN), Sichuan University (CN)
National Natural Science Foundation of China, Southwest University
Clean water and sanitation
Openalex Percentile: Top 91%
Radical Photochemical Reactions
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