Organic Chemistry Portal



Selective Cleavage of Inert Aryl C-N Bonds in N-Aryl Amides

Zhiguo Zhang*, Dan Zheng, Yameng Wan, Guisheng Zhang*, Jingjing Bi, Qingfeng Liu, Tongxin Liu and Lei Shi

*School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China, Email:,

Z. Zhang, D. Zheng, Y. Wan, G. Zhang, J. Bi, Q. Liu, Q. Liu, T. Liu, L. Shi, J. Org. Chem., 2018, 84, 1369-1376.

DOI: 10.1021/acs.joc.7b02880

see article for more reactions


IBX promotes a highly selective oxidative cleavage of inert C(aryl)-N bonds on secondary amides while leaving the C(carbonyl)-N bond unchanged. This metal-free reaction proceeds under mild conditions and provides facile access to various useful primary amides.

see article for more examples

proposed mechanism

Key Words

IBX, cleavage of amides

ID: J42-Y2018