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Condition-Controlled O-Acylation and N-O Bond Reduction of Hydroximic Acids with Thioacetic Acid

Risong Wang, Yifei Chen, Binjie Fei, Jiahao Hu, Jianhui Chen*, Yanshu Luo and Yuanzhi Xia*

*College of Chemistry and Materials Engineering, Wenzhou University, Wenzhou 325035, China, Email: cjhwzu.edu.cn, xyzwzu.edu.cn

R. Wang, Y. Chen, B. Fei, J. Hu, J. Chen, Y. Luo, Y. Xia, Org. Lett., 2023, 25, 2964-2969.

DOI: 10.1021/acs.orglett.3c00735


Abstract

The use of NH4HCO3 in ethanol as solvent enables an efficient N-O bond cleavage of hydroxamic acids in the presence of thioacetic acid to afford primary amides with high functional group compatibility, while O-acylation occurs when NEt3 as base and H2O as solvent were used. These facile transformations could be scaled up to the gram level smoothly.


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proposed mechanism



Key Words

reduction of hydroximic acids, thioacetic acid


ID: J54-Y2023