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CuI/Oxalic Diamide Catalyzed Coupling Reaction of (Hetero)Aryl Chlorides and Amines

Wei Zhou, Mengyang Fan, Junli Yin, Yongwen Jiang and Dawei Ma*

*State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Lu, Shanghai 200032, China, Email:

W. Zhou, M. Fan, J. Yin, Y. Jiang, D. Ma, J. Am. Chem. Soc., 2015, 137, 11942-11945.

DOI: 10.1021/jacs.5b08411 (free Supporting Information)


Bis(N-aryl) substituted oxalamides are effective ligands for promoting CuI-catalyzed aryl amination with less reactive (hetero)aryl chlorides at 120 C with K3PO4 as the base in DMSO to afford a wide range of (hetero)aryl amines in good to excellent yields. Both the electronic nature and the steric property of the aromatic groups of the ligands are important for their efficiency.

see article for more examples

Copper-Catalyzed Diaryl Ether Formation from (Hetero)aryl Halides at Low Catalytic Loadings

Y. Zhai, X. Chen, W. Zhou, M. Fan, Y. Lai, D. Ma, J. Org. Chem., 2017, 82, 4964-4969.

CuI/DMPAO-Catalyzed N-Arylation of Acyclic Secondary Amines

Y. Zhang, X. Yang, Q. Yao, D. Ma, Org. Lett., 2012, 14, 3056-3059.

Key Words

aryl amines, Ullmann coupling

ID: J48-Y2015