Issue 8, 2017

Selective C–N coupling reaction of diaryliodonium salts and dinucleophiles

Abstract

N-Aryl-α-amino amides including their chiral isomers have demonstrated important applications as pharmaceutical drugs; however, to date, a one-step synthetic route for them still remains to be developed. Herein, an efficient ligand-free copper-catalyzed selective C–N coupling reaction of diaryliodonium salts and dinucleophiles under mild conditions was realized. Diaryliodonium salts prefer to react with dinucleophiles at the site of stronger alkalic amino groups. Thus, a general aliphatic amino-selective N-arylation of α-amino amides was disclosed. Additionally, copper-catalyzed N-arylation of diaryliodonium salts afforded the same products as obtained via palladium-catalyzed reactions of aryl halides.

Graphical abstract: Selective C–N coupling reaction of diaryliodonium salts and dinucleophiles

Supplementary files

Article information

Article type
Letter
Submitted
16 Dec 2016
Accepted
06 Mar 2017
First published
07 Mar 2017

New J. Chem., 2017,41, 2873-2877

Selective C–N coupling reaction of diaryliodonium salts and dinucleophiles

C. Ma, X. Wu, Q. Zeng, L. Zhou and Y. Huang, New J. Chem., 2017, 41, 2873 DOI: 10.1039/C6NJ03964B

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