An Electrochemically Driven Oxidative Strecker Reaction via the Unique Hydroxymethyl Radical Intermediate

Alfa‐aminonitriles are versatile and valuable intermediates in pharmaceutical chemistry. Until now, the Strecker reaction has remained the most efficient tool for synthesizing these compounds. Nevertheless, it is only applicable to aldehyde/imine systems and generally needs metal catalysts and exter...

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Bibliographic Details
Published in:Advanced synthesis & catalysis 2024-05, Vol.366 (9), p.1983-1988
Main Authors: Chen, Cheng, Wang, Cen‐Xuan, Zhang, Guo‐Wei, Wu, Ming‐Yu, Feng, Shun
Format: Article
Language:English
Subjects:
Alcohols oxidation
Aldehydes
Alkylamines
Alkylation
Amines
Electrochemistry
Fuel cells
Functional groups
Reagents
Strecker reaction
α-Aminonitriles
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Summary:Alfa‐aminonitriles are versatile and valuable intermediates in pharmaceutical chemistry. Until now, the Strecker reaction has remained the most efficient tool for synthesizing these compounds. Nevertheless, it is only applicable to aldehyde/imine systems and generally needs metal catalysts and external additives. Herein, an electrochemically driven oxidative Strecker reaction strategy was designed and accomplished for the synthesis of α‐aminonitriles with alcohol as the alkylation reagent. The strategy is environmentally friendly, scalable, and compatible with a wide range of functional groups, encompassing aromatic primary amines, secondary amines, and even alkylamine. Utilizing the merits of electro‐organic synthesis, it can be readily magnified from milligram to gram scale by simply adjusting the electrochemical parameters. Emphasized, it testified that a unique intermediate CH2*OH well‐established in fuel cells was involved in the reaction.
ISSN:1615-4150
1615-4169
DOI:10.1002/adsc.202301465