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

---

see article for more reactions

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.

see article for more examples

proposed mechanism

---

---

Key Words

cleavage of amides, N-fluorobenzenesulfonimide

---

ID: J54-Y2020