Assembly of Primary (Hetero)Arylamines via CuI/Oxalic Diamide-Catalyzed Coupling of Aryl Chlorides and Ammonia

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

*State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China, Email: madwmail.sioc.ac.cn

M. Fan, W. Zhou, Y. Jiang, D. Ma, Org. Lett., 2015, 17, 5934-5937.

DOI: 10.1021/acs.orglett.5b03230

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Abstract

A general and practical aryl amination of aryl chlorides with aqueous or gaseous ammonia, CuI as the catalyst, and bisaryl oxalic diamides as the ligands proceeds at 105-120 °C to provide a diverse set of primary (hetero)aryl amines in high yields with various functional groups.

see article for more examples

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CuI/4-Hydro-L-proline as a More Effective Catalytic System for Coupling of Aryl Bromides with N-Boc Hydrazine and Aqueous Ammonia

L. Jiang, X. Lu, H. Zhang, Y. Jiang, D. Ma, J. Org. Chem., 2009, 74, 4542-4546.

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Key Words

anilines

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ID: J54-Y2015