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Copper-Catalyzed Radical N-Demethylation of Amides Using N-Fluorobenzenesulfonimide as an Oxidant

Xuewen Yi, Siyu Lei, Wangsheng Liu, Fengrui Che, Chunzheng Yu, Xuesong Liu, Zonghua Wang*, Xin Zhou and Yuexia Zhang*

*College of Chemistry and Chemical Engineering, Qingdao University, 308 Ningxia Road, Qingdao 266071, China, Email: wangzonghuaqdu.edu.cn, zhangyxqdu.edu.cn

X. Yi, S. Lei, W. Liu, F. Che, C. Yu, X. Liu, Z. Wang, X. Zhou, Y. Zhang, Org. Lett., 2020, 22, 4583-4587.

DOI: 10.1021/acs.orglett.0c00863 (free Supporting Information)


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Abstract

Cu(acac)2 catalyzes an unprecedented N-demethylation of N-methyl amides in the presence of N-fluorobenzenesulfonimide as an oxidant. The reaction involves carbinolamines as intermediates, that spontaneously decompose to N-demethylated amides and formaldehyde, because of their inherent instability.


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proposed mechanism



Key Words

cleavage of amides, N-fluorobenzenesulfonimide


ID: J54-Y2020