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Selective C–N coupling reaction of diaryliodonium salts and dinucleophiles

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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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Publication details

The article was received on 16 Dec 2016, accepted on 06 Mar 2017, published on 07 Mar 2017 and first published online on 07 Mar 2017


Article type: Letter
DOI: 10.1039/C6NJ03964B
Citation: New J. Chem., 2017, Advance Article
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    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, Advance Article , DOI: 10.1039/C6NJ03964B

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