Electrochemical Synthesis of Polysubstituted Oxazoles from Ketones and Acetonitrile

Herein we report an electrochemical strategy for the construction of polysubstituted oxazoles from easily available ketones and acetonitrile under room temperature. The method shows high efficiency, a broad substrate scope, and requires no external chemical oxidant. Mechanistic investigations sugges...

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Bibliographic Details
Published in:Organic letters 2022-08, Vol.24 (31), p.5762-5766
Main Authors: Bao, Liang, Liu, Chen, Li, Wenyi, Yu, Jiage, Wang, Min, Zhang, Yunfei
Format: Article
Language:English
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Summary:Herein we report an electrochemical strategy for the construction of polysubstituted oxazoles from easily available ketones and acetonitrile under room temperature. The method shows high efficiency, a broad substrate scope, and requires no external chemical oxidant. Mechanistic investigations suggest that the reaction proceeds through a Ritter-type reaction/oxidative cyclization using acetonitrile as the reactant and solvent. X-ray crystallographic analysis reveals that the reaction involves the attack of acetonitrile on the carbonyl carbon instead of the α-carbon.
ISSN:1523-7060
1523-7052
DOI:10.1021/acs.orglett.2c02252