Selective C–N coupling reaction of diaryliodonium salts and dinucleophiles?

New Journal of Chemistry Pub Date: 2017-03-07 DOI: 10.1039/C6NJ03964B

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
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