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Discovery of N-(Naphthalen-1-yl)-N'-alkyl Oxalamide Ligands Enables Cu-Catalyzed Aryl Amination with High Turnovers

Jie Gao, Subhajit Bhunia, Kailiang Wang, Lu Gan, Shanghua Xia and Dawei Ma*

*Interdisciplinary Center on Biology and Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 26 Qiuyue Lu, Shanghai 201210, China, Email: madwsioc.ac.cn

J. Gao, S. Bhunia, K. Wang, L. Gan, S. Xia, D. Ma, Org. Lett., 2017, 19, 2809-2812.

DOI: 10.1021/acs.orglett.7b00901 (free Supporting Information)


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Abstract

A class of N-(naphthalen-1-yl)-N'-alkyl oxalamides are powerful ligands in Cu-catalyzed coupling reactions of (hetero)aryl iodides and bromides with primary amines or ammonia. A wide range of coupling partners work well under these conditions.

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

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

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

Ullmann reaction, amination


ID: J54-Y2017